AU5977200A - Substituted ureas - Google Patents

Substituted ureas Download PDF

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Publication number
AU5977200A
AU5977200A AU59772/00A AU5977200A AU5977200A AU 5977200 A AU5977200 A AU 5977200A AU 59772/00 A AU59772/00 A AU 59772/00A AU 5977200 A AU5977200 A AU 5977200A AU 5977200 A AU5977200 A AU 5977200A
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AU
Australia
Prior art keywords
alkyl
alkoxy
haloalkyl
hydrogen
carbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
AU59772/00A
Inventor
Klaus Grossmann
Gerhard Hamprecht
Olaf Menke
Martina Otten
Michael Puhl
Robert Reinhard
Ingo Sagasser
Helmut Walter
Karl-Otto Westphalen
Cyrill Zagar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of AU5977200A publication Critical patent/AU5977200A/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines

Description

1 Substituted ureas The present invention relates to substituted ureas having a 5 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. 10 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. 15 J5 [sic] 9082-372 describes herbicidally active tetrahydropyridazinecarboxylic acid derivatives and processes for their preparation. 20 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 25 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 30 undesirable vegetation using the compounds I. Accordingly, the present invention relates to substituted ureas of the formula Ia and Ib 35 xx (RA)m N NZ C-NH N (RA)m> R 40 la Ib in which the variables X, Z, m, R and RA are as defined below: 45 X is S or 0; 2 Z is 0, S, S=0 or S02; m has the value 0, 1, 2 or 3; 5 R is hydrogen, C(O)OR 10 , C(O)SR 1 0, C(S)OR 10 , C(S)SR 1 0, CO 2 H, CHO, cyano, C(O)NR 11
R
12 , C(S)NR 11
R
12 , C(O)NHC(O)Cl,
C(O)NHS(O)
2 Cl, C(O)NHC(O)OR 12 ', C(O)NHS(O) 2
R
12 ',
C(O)NHS(O)
2 OR1 2 ', C(O)R 2 , P(O)R(ORI), P(O)(ORI) 2 , S(O)nR 2 where n = 0, 1 or 2, or SO 2
NHR
1 ; 10 RA is hydroxyl, C0 2
R
1 , halogen, cyano, C(O)N(RI) 2 , where the radicals R 1 are, if appropriate, different from one another, is OR 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
3
-C
6 -alkenyl, C 3
-C
6 -alkynyl, COR 1 , S(O)nRI where n = 0, 1 15 or 2, or is C(O)SR1; Q is one of the radicals 01 to 06: 3 3 3 20 20/\ R4 R4 R4 Rs Y N N Y
UR
6
UR
6 25 0-1 0-2 0-3 3 3 3 30 Y Y R4 N N Y' O0
TR
7
TR
7 35 R R 9 0-4 0-5 0-6 in which 40 Y and Y' independently of one another are 0 or S; T is a chemical bond or 0; 45 U is a chemical bond, C1-C 4 -alkylene, 0, S, SO or SO 2
;
3 and the radicals RI to R 3 0 are as defined below:
R
1 is hydrogen, C 1
-C
6 -alkyl, C 1
-C
6 -haloalkyl,
CI-C
3 -alkoxy-Ci-C 3 -alkyl, C 3
-C
6 -alkenyl or C 3
-C
6 -alkynyl; 5
R
2 is Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, Ci-C 6 -haloalkyl, CI-C 6 -alkoxy-Ci-C 6 -alkyl, hydroxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, 10 Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfinyl-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl-Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl,
C
3
-C
6 -cycloalkyl-Ci-C 6 -alkyl,
C
3
-C
6 -alkenyloxycarbonyl-Ci-C 6 -alkyl, 15 C 3
-C
6 -alkynyloxycarbonyl-Ci-C 6 -alkyl,
C
3
-C
6 -cycloalkoxy-Ci-C 6 -alkyl,
C
3
-C
6 -alkenyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -alkynyloxy-C 1
-C
6 -alkyl, Ci-C 6 -haloalkoxy-Ci-C 6 -alkyl, 20 C 3
-C
6 -haloalkenyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -haloalkynyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -cycloalkyl-Ci-C 6 -thioalkyl,
C
3
-C
6 -alkenylthio-Ci-C 6 -alkyl,
C
3
-C
6 -alkynylthio-C 1
-C
6 -alkyl, cyano-Ci-C 6 -alkyl, 25 C 3
-C
6 -halocyclo-Ci-C 6 -alkyl [sic], halo-C 2
-C
6 -alkenyl, Ci-C 6 -alkoxy-C 3
-C
6 -alkenyl,
C
1
-C
6 -haloalkoxy-C 3
-C
6 -alkenyl,
C
1
-C
6 -alkylthio-C 3
-C
6 -alkenyl, C 3
-C
6 -haloalkynyl,
C
1
-C
6 -alkoxy-C 3
-C
6 -alkynyl, 30 Ci-C6-haloalkoxy-C 3
-C
6 -alkynyl,
CI-C
6 -alkylthio-C 3
-C
6 -alkynyl, Ci-C 6 -alkylcarbonyl,
CHRICOR
7 , CHRIP(O)(OR 7
)
2 , P(O)(OR 7
)
2 , CHRIP(S)(OR 7
)
2 , CHRIC(O)NRilR 12 , CHRIC(O)NH 2 , phenoxy-Ci-C 6 -alkyl or benzyloxy-Ci-C 6 -alkyl, where the benzene rings of the two 35 last-mentioned groups may for their part be substituted by halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl; is benzyl which may be substituted by halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl or is phenyl or pyridyl, each of which may be substituted by halogen, Ci-C 4 -alkyl, 40 Ci-C 4 -haloalkyl or Ci-C 4 -alkoxy;
R
3 is hydrogen or halogen;
R
4 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OCH 3 , SCH 3 , OCHF 2 , 45 halogen, cyano or NO 2
;
4
R
5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, Ci-C 6 -alkyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkynyl, Ci-C 6 -haloalkyl, C 1
-C
6 -haloalkoxy, Ci-C 6 -haloalkylthio, Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)carbonyl, 5 Ci-C 6 -alkylthio-(Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkyl)iminooxycarbonyl, C 1
-C
6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxyamino-CI-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkylamino-Ci-C 6 -alkyl, 10 is C 1
-C
6 -alkoxy, Ci-C 6 -alkylthio, C 3
-C
6 -cycloalkoxy,
C
3
-C
6 -cycloalkylthio, C 2
-C
6 -alkenyloxy, C 2
-C
6 -alkenylthio,
C
2
-C
6 -alkynyloxy, C 2
-C
6 -alkynylthio, (Ci-C 6 -alkyl)carbonyloxy, (C 1
-C
6 -alkyl)carbonylthio, (Ci-C 6 -alkoxy)carbonyloxy, (C 2
-C
6 -alkenyl)carbonyloxy, 15 (C 2
-C
6 -alkenyl)carbonylthio, (C 2
-C
6 -alkynyl)carbonyloxy,
(C
2
-C
6 -alkynyl)carbonylthio, Ci-C 6 -alkylsulfonyloxy or
C
1
-C
6 -alkylsulfonyl, where each of the 17 last-mentioned radicals may, if desired, carry one, two or three substituents selected from the group consisting of: 20 - halogen, nitro, cyano, hydroxyl, C 3
-C
6 -cycloalkyl, Ci-C 6 -alkoxy, C 3
-C
6 -cycloalkoxy, C 3
-C
6 -alkenyloxy,
C
3
-C
6 -alkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, C1-C 6 -alkylsulfinyl, 25 C 1
-C
6 -alkylsulfonyl, Ci-C 6 -alkylideneaminooxy, oxo, =N-OR13; - phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned groups may carry one, two or three 30 substituents selected from the group consisting of halogen, nitro, cyano, C 1
-C
6 -alkyl, C 1
-C
6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; - -CO-R 14 , -CO-OR 1 4 , -CO-SR 1 4 , -CO-N(R1 4
)-R
1 5 , -OCO-R 1 4 , 35 -OCO-OR 1 4 ', -OCO-SR 1 4 ', -OCO-N(R 1 4 )-R1 5 , -N(R 1 4
)-R
1 5 , and -C(R 1 6
)=N-OR
1 3 ; C(Zl)-R 1 7 , -C(=NR1 8
)R
1 7 , C(R 1 7
)(Z
2 R1 9
)(Z
3
R
2 0 ),
C(R
1 7
)=C(R
2 1 )-CN, C(R 1 7
)=C(R
2 1
)-CO-R
2 2 , 40 -CH(R 1 7
)-CH(R
2 1
)-COR
2 2 , -C(R1 7
)=C(R
2 1
)-CH
2
-CO-R
2 2 ,
-C(R
1 7
)=C(R
2 1
)-C(R
2 3
)=C(R
2 4
)-CO-R
2 2 , -C(R1 7
)=C(R
2 1
)-CH
2
-CH(R
2 5
)-CO-R
2 2 , -CO-OR 2 6 , -CO-SR 2 6 ,
-CON(R
2 6
)-OR
1 3 , -C-C-CO-NHOR 1 3 , -CsC-CO-N(R 2 6
)-OR
1 3 , -CaC-CS-NH-OR 1 3 , -C-C-CS-N(R 2 6
)-OR
1 3 , 45 -C(R 1 7
)=C(R
2 1
)-CO-NHOR
1 3 , -C(R 1 7
)=C(R
2 1
)-CO-N(R
2 6
)-OR
1 3 ,
-C(R
1 7
)=C(R
2 1
)-CS-NHOR
1 3 , -C(R 1 7
)=C(R
2 1
)-CS-N(R
2 6
)-OR
1 3 ,
-C(R
1 7
)=C(R
2 1
)-C(R
1 6
)=N-OR
1 3 , C(R 1 6
)=N-OR
1 3
,
5
-C=C-C(R
1 6 )=NORi 3 , C(Z 2
R
1 9
)(Z
3
R
2 0
)-OR
2 6 ,
-C(Z
2
R
1 9
)(Z
2
R
2 0
)SR
2 6 , C(Z 2
R
1 9
)(Z
3
R
2 0
)-N(R
2 7
)R
2 8 , -N(R 2 7
)-R
2 8 , -CO-N(R27)-R28 or -C(R1 7
)=C(R
2 1
)CO-N(R
2 7
)R
2 8 ; where Zl, Z 2 ,
Z
3 independently of one another are oxygen or sulfur; 5
R
6 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 3 -alkoxy-Ci-C 3 -alkyl, C 3
-C
6 -alkenyl, Ci-C 3 -alkoxy-C 3
-C
6 -alkenyl, C 3
-C
6 -haloalkenyl,
C
3
-C
6 -alkynyl, Ci-C 3 -alkoxy-C 3
-C
6 -alkynyl, 10 C 3
-C
6 -haloalkynyl, C 3
-C
7 -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 15 substitutents, selected from the group consisting of cyano, nitro, amino, hydroxyl, halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -cyanoalkyl, Ci-C 4 -hydroxyalkyl, Ci-C 4 -aminoalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, 20 Ci-C 4 -alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, (Ci-C 4 -alkoxy)carbonyl, (Ci-C 4 -alkyl)carbonyl, (Ci-C 4 -haloalkyl)carbonyl, (Ci-C 4 -alkyl)carbonyloxy, (Ci-C4-haloalkyl)carbonyloxy, di(Ci-C 4 -alkyl)amino,
C
3
-C
6 -alkenyl, C 3
-C
6 -alkynyl, C 3
-C
4 -alkenyloxy, 25 C 3
-C
4 -alkenylthio, C 3
-C
4 -alkynyloxy and C 3
-C
4 -alkynylthio;
R
7 is hydrogen, Ci-C 6 -alkyl, CI-C 6 -haloalkyl, Ci-C 3 -alkoxy-Ci-C 3 -alkyl, C 2
-C
6 -cyanoalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl; 30
R
8 is hydrogen, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl or halogen;
R
9 is hydrogen, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl; or 35 R 8 and R 9 together are C=O;
R
10 is Ci-C 15 -alkyl, C 3
-C
8 -cycloalkyl, C 2
-C
1 0 -alkenyl,
C
3
-C
1 0 -alkynyl, CI-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, 40 Ci-C 6 -alkylsulfinyl-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl-Ci-C 6 -alkyl, Ci-C3-alkoxy-Cl-C 3 -alkoxy-Ci-C 3 -alkyl,
C
3
-C
6 -cycloalkyl-Ci-C 6 -alkyl, carboxyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, 45 Ci-C 6 -alkoxycarbonyl-C 2
-C
6 -alkenyl,
C
3
-C
6 -alkenyloxycarbonyl-Ci-C 6 -alkyl,
C
3
-C
6 -alkynyloxycarbonyl-Ci-C 6 -alkyl, 6
C
3
-C
8 -cycloalkoxy-Ci-C 6 -alkyl,
C
3
-C
6 -alkenyloxy-C 1
-C
6 -alkyl,
C
3
-C
6 -alkynyloxy-C 1
-C
6 -alkyl, Ci-C 6 -haloalkoxy-Ci-C6 -alkyl, 5 C 3
-C
6 -haloalkenyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -haloalkynyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -cycloalkyl-Ci-C 6 -thioalkyl,
C
3
-C
6 -alkenylthio-Ci-C 6 -alkyl,
C
3
-C
6 -alkynylthio-C 1
-C
6 -alkyl, cyano-Ci-C 6 -alkyl, 10 C 3
-C
6 -halocyclo-Ci-C 6 -alkyl, halo-C 3
-C
6 -alkenyl,
C
1
-C
6 -alkoxy-C 3
-C
6 -alkenyl,
CI-C
6 -haloalkoxy-C 3
-C
6 -alkenyl, Ci-C 6 -alkylthio-C 3
-C
6 -alkenyl, C 3
-C
6 -haloalkynyl,
C
1
-C
6 -alkoxy-C 3
-C
6 -alkynyl, 15 Ci-C 6 -haloalkoxy-C 3
-C
6 -alkynyl,
CI-C
6 -alkylthio-C 3
-C
6 -alkynyl, CHRICOR 7 , CHR 1
P(O)(OR
7 )2,
P(O)(OR
7
)
2 , CHRP(S)(OR 7
)
2 , CHR 1
C(O)NR
1 1 R1 2 , CHRIC(O)NH 2 , Ci-C 6 -alkyl, which is substituted by phenoxy or benzyloxy, where the benzene rings of the two 20 last-mentioned groups may for their part be substituted by halogen, C 1
-C
4 -alkyl or Ci-C 4 -haloalkyl; is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 25 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzthiazolyl, benzyl, which may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which 30 may in each case be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, amino, Ci-C 4 -monoalkylamino, Ci-C 4 -dialkylamino,
C
3
-C
6 -cycloalkyl, Ci-C 4 -alkoxycarbonyl, 35 Ci-C 4 -alkoxycarbonyl-Ci-C 4 -alkyl, hydroxyl, nitro or cyano;
R
11 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy; 40 R 12 is hydrogen, Ci-C 6 -alkyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkynyl,
C
3
-C
6 -cycloalkyl, C-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C6 -alkyl, Ci-C 6 -alkoxycarbonyl-C 2
-C
6 -alkenyl, where the alkenyl 45 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, 7 difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, 5 Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, amino, Ci-C 4 -monoalkylamino, Ci-C 4 -dialkylamino,
C
3
-C
6 -cycloalkyl, Ci-C 4 -alkoxycarbonyl, Ci-C4-alkoxycarbonyl-Cl-C 4 -alkyl, hydroxyl, nitro or cyano 10 or
R
11 and R 12 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 15 desired, contain one of the following members: -0-, -S-, -N=, -NH- or N-(Ci-C 6 -alkyl)-;
R
12 ' is as defined for R 12 , but excluding hydrogen; 20 R 13 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl, C 3
-C
6 -alkynyl, hydroxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkyl, 25 (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-C 2
-C
6 -alkenyl, (Ci-C6-alkyl)carbonyloxy-Ci-C 6 -alkyl or phenyl-Ci-C 6 -alkyl, in which the phenyl ring may, if desired, carry one, two or three substituents selected 30 from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl;
R
14 is hydrogen, Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl, 35 C 3
-C
6 -alkynyl, C 1
-C
6 -alkoxy-C 1
-C
6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, (C3-C6-alkenyloxy)carbonyl-Ci-C 6 -alkyl, phenyl or phenyl-Ci-C 6 -alkyl, where the phenyl ring of the two last-mentioned groups may be unsubstituted or may carry 40 one, two or three radicals selected from the group consisting of halogen, nitro, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkyl)carbonyl;
R
14 ' is as defined for R 14 , but excluding hydrogen; 45 8
R
1 5 is hydrogen, hydroxyl, Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Cl-C 6 -alkoxy,
C
3
-C
6 -alkenyl or C 3
-C
6 -alkenyloxy; 5 R 16 is hydrogen, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3
-C
6 -alkenyloxy,
C
3
-C
6 -alkynyloxy, Ci-C 6 -alkylthio, Ci-C 6 -haloalkylthio, (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -haloalkyl)carbonyloxy, Ci-C 6 -alkylsulfonyloxy or Ci-C 6 -haloalkylsulfonyloxy, 10 where the 12 last-mentioned radicals may carry one of the following substituents: hydroxyl, cyano, hydroxycarbonyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkyl)aminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, (Ci-C 6 -alkyl)carbonyloxy, 15 Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)aminocarbonyl; is (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -haloalkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkoxy)carbonyloxy, (Ci-C 6 -alkyl)carbonylthio, (Ci-C 6 -haloalkyl)carbonylthio, 20 (Ci-C 6 -alkoxy)carbonylthio, C 2
-C
6 -alkenyl,
(C
2
-C
6 -alkenyl)carbonyloxy, C 2
-C
6 -alkenylthio,
C
3
-C
6 -alkynyl, C 3
-C
6 -alkynyloxy, C 3
-C
6 -alkynylthio,
(C
2
-C
6 -alkynyl)carbonyloxy, C3-C 6 -alkynylsulfonyloxy,
C
3
-C
6 -cycloalkyl, C 3
-C
6 -cycloalkyloxy, 25 C 3
-C
6 -cycloalkylthio, (C 3
-C
6 -cycloalkyl)carbonyloxy,
C
3
-C
6 -cycloalkylsulfonyloxy; is phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-Ci-C 6 -alkyl, 30 phenyl-Ci-C 6 -alkoxy, phenyl-Ci-C 6 -alkylthio, phenyl-(Ci-C 6 -alkyl)carbonyloxy or phenyl-(Ci-C 6 -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 35 each case selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl;
R
1 7 is hydrogen, cyano, CI-C 6 -alkyl, Ci-C 6 -haloalkyl, 40 C 2
-C
6 -alkenyl, C 2
-C
6 -alkynyl, C 3
-C
6 -cycloalkyl,
C
1
-C
6 -alkoxy-Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl;
R
18 is hydrogen, hydroxyl, C 1
-C
6 -alkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, C 3
-C
6 -cycloalkyl, Ci-C 6 -haloalkyl, 45 Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3
-C
6 -alkenyloxy,
C
3
-C
6 -alkynyloxy, C 3
-C
6 -cycloalkoxy,
C
5
-C
7 -cycloalkenyloxy, Ci-C 6 -haloalkoxy, 9
C
3
-C
6 -haloalkenyloxy, hydroxy-Ci-C 6 -alkoxy, cyano-Ci-C 6 -alkoxy, C3-C 6 -cycloalkyl-Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C6-alkoxy-C 3
-C
6 -alkenyloxy, (Ci-C 6 -alkyl)carbonyloxy, (Ci-C6-haloalkyl)carbonyloxy, 5 (Ci-C 6 -alkyl)carbamoyloxy, (Ci-C6-haloalkyl)carbamoyloxy, (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkoxy, 10 Ci-C 6 -alkylthio-Ci-C 6 -alkoxy, di(Ci-C 6 -alkyl)amino-Ci-C 6 -alkoxy, -N(R 9
)R
30 [sic], phenyl which for its part may carry one, two or three substituents, in each case selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, 15 Ci-C 6 -haloalkyl, C 2
-C
6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; is phenyl-C 1
-C
6 -alkoxy, phenyl-(Ci-C 6 -alkyl), phenyl-C 3
-C
6 -alkenyloxy or phenyl-C 3
-C
6 -alkynyloxy, where 20 in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -0-, -S- or -N(Ci-C 6 -alkyl)- and where the phenyl rings in the four last-mentioned groups may be unsubstituted or may for their part carry one to three 25 substituents, selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
2
-C
6 -alkenyl, CI-C 6 -alkoxy and (Ci-C6-alkoxy)carbonyl; is C 3
-C
7 -heterocyclyl, C3-C7-heterocyclyl-Ci-C 6 -alkyl, 30 C3-C 7 -heterocyclyl-Ci-C 6 -alkoxy, C3-C7-heterocyclyl-C 3
-C
6 -alkenyloxy or C3-C7-heterocyclyl-C 3
-C
6 -alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -0-, -S- or 35 -N(Ci-C 6 -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, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, 40 C 2
-C
6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl;
R
19 , R 2 0 independently of one another are Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl, C3-C6-alkynyl, Ci-C 6 -alkoxy-CI-C 6 -alkyl or together are a saturated or 45 unsaturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a member of this chain which is not adjacent co the variables Z 2 and Z 3 may be replaced 10 by -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)- and where the carbon chain may carry one to three substituents selected from the group consisting of cyano, nitro, amino, halogen, Ci-C 6 -alkyl, C 2
-C
6 -alkenyl, Ci-C 6 -alkoxy, 5 C 2
-C
6 -alkenyloxy, C 2
-C
6 -alkynyloxy, Ci-C 6 -haloalkyl, cyano-Ci-C 6 -alkyl, hydroxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, C 3
-C
6 -alkenyloxy-Ci-C 6 -alkyl,
C
3
-C
6 -alkynyloxy-C 1
-C
6 -alkyl, C 3
-C
6 -cycloalkyl,
C
3
-C
6 -cycloalkoxy, carboxyl, (Ci-C 6 -alkoxy)carbonyl, 10 (Ci-C 6 -alkyl)carbonyloxy-Ci-C 6 -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 15 group consisting of oxygen, sulfur, nitrogen and Cl-C 6 -alkyl-substituted nitrogen and which may for its part, if desired, carry one or two of the following substituents: cyano, CI-C 6 -alkyl, C 2
-C
6 -alkenyl, Ci-C 6 -alkoxy, cyano-Ci-C 6 -alkyl, Ci-C 6 -haloalkyl and 20 (Ci-C 6 -alkoxy)carbonyl;
R
21 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkyl)carbonyl or (Ci-C 6 -alkoxy)carbonyl; 25
R
22 is hydrogen, O-R 3 1 , S-R 3 1 , Ci-C 6 -alkyl which may carry one or two Ci-C 6 -alkoxy substituents, is C 2
-C
6 -alkenyl,
C
2
-C
6 -alkynyl, Ci-C 6 -haloalkyl, C 3
-C
6 -cycloalkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkyliminooxy, 30 -N(R 2 7
)R
2 8 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, Ci-C 6 -alkyl, C 2
-C
6 -alkenyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; 35
R
23 is hydrogen, cyano, halogen, CI-C 6 -alkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, -N(R 2 7
)R
2 8 or phenyl which for its part may carry one to three 40 substituents selected from the group consisting of cyano, nitro, halogen, CI-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
3
-C
6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl;
R
24 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, 45 Ci-C 6 -haloalkyl, (Ci-C 6 -alkyl)carbonyl or (Ci-C 6 -alkoxy)carbonyl; 11
R
25 is hydrogen, cyano, Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl;
R
26 , R 31 independently of one another are hydrogen,
CI-C
6 -alkyl, Ci-C 6 -haloalkyl, C 2
-C
6 -alkenyl or 5 C 2
-C
6 -alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkyl)carbonyloxy, 10 (C 3
-C
6 -alkenyloxy)carbonyl; are (Ci-C 6 -haloalkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, Ci-C 6 -alkyloximino-Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl; 15 are phenyl or phenyl-Ci-C 6 -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, Ci-C 6 -alkyl, 20 Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl;
R
27 , R 2 8 , R 29 , R 3 0 independently of one another are hydrogen, Ci-C 6 -alkyl, C 3
-C
6 -alkenyl, C 2
-C
6 -alkynyl,
C
3
-C
6 -cycloalkyl, Ci-C 6 -haloalkyl, 25 Ci-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, are (Ci-C 6 -alkoxy)carbonyl-C 2
-C
6 -alkenyl, where the 30 alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are Ci-C 6 -alkylsulfonyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkylsulfonyl, phenyl or phenylsulfonyl, where the phenyl rings of the two last-mentioned radicals may be unsubstituted or may for 35 their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, CI-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl,
CI-C
6 -alkoxy and (Cl-C 6 -alkoxy)carbonyl; or 40 R 27 and R 2 8 and/or
R
29 and R 30 together with the respective common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, 45 may, if desired, contain one of the following members: -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)-; 12 and the agriculturally useful salts of the compounds Ia and Ib. Such compounds are provided by the present invention, except for 5 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 Ql in which R 3 = fluorine and R 4 = chlorine, and R 5 is selected from the group consisting of isopropoxy, propargyloxy, allyloxy, benzyloxy and isopropoxycarbonyl, hydroxyiminomethyl, 10 methoxyiminomethyl,
CH=NOCH
2
CO
2
CH
3 , -CH=N-0-C(CH 3
)
2
-CO
2
CH
3 , propargyloxyiminomethyl, -CH=C(Cl)-CO 2
CH
3 , -CH=C(Cl)C0 2
C
2
H
5 , -CH=C(Cl)-C0 2
-CH
2
-CO
2
CH
3 , -CH=C(Cl)-C0 2
-CH(CH
3
)CO
2
CH
3 , -CH=C(Cl)-C0 2
-CH
2
-CO
2 -tert-butyl, -CH=C(Cl)-CO 2 H, -CH=C(Cl)-CONHOCH 3 , -CH=C(Cl)-CONHOC 2
H
5 or -CH=N-0-CH(CH 3
)-CO
2
CH
3 ; 15 or Q is a radical of the formula Ql where R 3 = R 5 [sic] = hydrogen and R 5 = chlorine, or Q is a radical of the formula Ql where R 3 = R4 = chlorine and R5 = H, methoxyiminomethyl, -CH=C(Cl)CO 2 H or -CH=C(Cl)-CO 2
C(CH
3
)
3 ; furthermore excluding compounds of the formula Ia in which Z is 20 oxygen and X is sulfur, m has the value 0, R is hydrogen and Q is a radical of the formula Q4 where R 3 = fluorine, Y = oxygen and
T-R
7 = propargyl, allyl or 3-(ethoxycarbonyl)prop-2-yl or Q is a radical [lacuna] Q1 where R 3 = R4 = chlorine and R 5 = hydrogen; 25 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. 30 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 35 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 40 transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which may, if desired, carry one to four Ci-C 4 -alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore 45 phosphonium ions, sulfonium ions, preferably 13 tri(Ci-C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C 4 -alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, 5 bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by 10 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 R 1 15 to R 2 , R 4 to R 3 1 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. 20 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. 25 Examples of other meanings are: - Ci-C 4 -alkyl: CH 3 , C 2
H
5 , n-propyl, CH(CH 3
)
2 , n-butyl,
CH(CH
3
)-C
2
H
5 , 2-methylpropyl or C(CH 3
)
3 , in particular CH 3 , 30 C 2
H
5 or CH(CH 3
)
2 ; - Ci-C 4 -haloalkyl: a CI-C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, CH 2 F, 35 CHF 2 , CF 3 , CH 2 Cl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 40 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C 2
F
5 , 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, 45 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1L-(chloromethy-l)-2-ch loru.oethI-yl, 1-(bromomethyl)-2-bromnoeth~yl, 14 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular CH 2 F, CHF 2 , CF 3 , CH 2 Cl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl; 5 - Ci-C 6 -alkyl: Ci-C 4 -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, 10 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 CH 3 , C 2
H
5 , n-propyl, 15 CH(CH 3
)
2 , n-butyl, C(CH 3
)
3 , n-pentyl or n-hexyl; - Ci-C 1 5 -alkyl: C 1
-C
6 -alkyl as mentioned above, and also, for example, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 20 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, 25 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, 30 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, 35 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, 40 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, 1,1-dimethylundecyl, n-tetradecyl, 1-methyltridecyl, 1-ethyldodecyl, 45 1,1-dimethyldodecyl, n-pentadecyl, 1-methyltetradecyl, 1-ethyltridecyl, 1,1-dimethyltridecyl, in particular CH 3 , - C 2H51' n-propyl, CH(CH3)2, i-uy,(C33 -pentyl, ni-Iexyl, 15 n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl; - CI-C 6 -haloalkyl: Ci-C 6 -alkyl as mentioned above which is 5 partially or fully substituted by fluorine, chlorine, bromine and/ [sic] iodine, i.e., for example, one of the radicals mentioned under Ci-C 4 -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-l-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl; 15 - hydroxy-Ci-C 6 -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, 20 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-Ci-C 6 -alkyl: for example cyanomethyl, 1-cyanoeth-1-yl, 25 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, 30 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or 2-cyanomethylprop-2-yl, in particular cyanomethyl or 2-cyanoethyl; - phenyl-Ci-C 6 -alkyl: for example benzyl, 1-phenylethyl, 35 2-phenylethyl, 1-phenylprop-1-yl, 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 40 or 1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl; - phenyl-(Ci-C 6 -alkyl)carbonyloxy: for example benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 45 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy, 1-phenylisut-1-ylcarbonyloxy, 2-phenylbut-i-ylearbonyloxy,- 16 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, 5 1-(phenylmethyl)-1-(methyl)eth-1-ylcarbonyloxy or 1-(phenylmethyl)prop-1-ylcarbonyloxy, in particular benzylcarbonyloxy or 2-phenylethylcarbonyloxy; - phenyl-Ci-C 6 -alkylsulfonyloxy: for example benzylsulfonyloxy, 10 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, 15 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 20 benzylsulfonyloxy or 2-phenylethylsulfonyloxy; - (Ci-C 6 -alkyl)carbonyl: CO-CH 3 , CO-C 2
H
5 , n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 25 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 30 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 35 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular CO-CH 3 , CO-C 2
H
5 or CO-CH(CH 3
)
2 ; 40 - (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by (Ci-C 6 -alkyl)carbonyl as mentioned above, i.e., for example, methylcarbonylmethyl; 45 - (Ci-C 6 -haloalkyl)carbonyl: a (Ci-C 6 -alkyl)carbonyl radical as mentioned above which is partially or fully substituted by fluorine, chluriie, bromine and/or iodine, i.e., for example, 17 chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 5 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 10 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 15 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 20 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, 25 (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 30 or dodecafluorohexylcarbonyl, in particular trifluoroacetyl; (Ci-C 6 -alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 35 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, 40 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, 45 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2, 2-trimetiylpropy.carbonyloxy, 18 1-ethyl-1-methylpropylcarbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, in particular acetyloxy; - (Ci-C 6 -haloalkyl)carbonyloxy: a (Ci-C 6 -alkyl)carbonyloxy 5 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, 10 dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 15 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 20 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, 25 2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoroethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy, 1-(bromomethyl)-2-bromoethylcarbonyloxy, 30 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, in particular trifluoroacetoxy; - (Ci-C 6 -alkyl)carbonyloxy-Ci-C 6 -alkyl: CI-C 6 -alkyl which is 35 substituted by (Ci-C 6 -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, 40 5-(methoxycarbonyloxy)pentyl or 6-(methoxycarbonyloxy)hexyl; - (Ci-C 6 -alkyl)carbonylthio: acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 45 2-methylpropylcarbonylthio, 1,1-dimethylethylcarbonylthio, n-pentylcarbonylthio, 1-methylbutylcarbonylthio, 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 19 1,1-dimethylpropylcarbonylthio, 1,2-dimethylpropylcarbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio, 5 2-methylpentylcarbonylthio, 3-methylpentylcarbonylthio, 4-methylpentylcarbonylthio, 1,1-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio, 1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio, 1-ethylbutylcarbonylthio, 10 2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio, 1,2,2-trimethylpropylcarbonylthio, 1-ethyl-1-methylpropylcarbonylthio or 1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio; 15 - (Ci-C 6 -haloalkyl)carbonylthio: a (Ci-C 6 -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, 20 trifluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio, 2,2-difluoroethylcarbonylthio, 25 2,2,2-trifluoroethylcarbonylthio, 2-chloro-2-fluoroethylcarbonylthio, 2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio, 30 pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio, 2,3-difluoropropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 35 3,3,3-trifluoropropylcarbonylthio, 3,3,3-trichloropropylcarbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio, 1-(fluoromethyl)-2-fluoroethylcarbonylthio, 40 1-(chloromethyl)-2-chloroethylcarbonylthio, 1-(bromomethyl) 2-bromoethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, in particular trifluoroacetylthio; 45 - (Ci-C 6 -alkyl)carbamoyloxy: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, i-iethylethylcarijamoyloxy, n-butylcarbamoyioxy, 20 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1,1-dimethylethylcarbamoyloxy, n-pentylcarbamoyloxy, 1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy, 3-methylbutylcarbamoyloxy, 1,1-dimethylpropylcarbamoyloxy, 5 1,2-dimethylpropylcarbamoyloxy, 2,2-dimethylpropylcarbamoyloxy, 1-ethylpropylcarbamoyloxy, n-hexylcarbamoyloxy, 1-methylpentylcarbamoyloxy, 2-methylpentylcarbamoyloxy, 3-methylpentylcarbamoyloxy, 4-methylpentylcarbamoyloxy, 1,1-dimethylbutylcarbamoyloxy, 10 1,2-dimethylbutylcarbamoyloxy, 1,3-dimethylbutylcarbamoyloxy, 2,2-dimethylbutylcarbamoyloxy, 2,3-dimethylbutylcarbamoyloxy, 3,3-dimethylbutylcarbamoyloxy, 1-ethylbutylcarbamoyloxy, 2-ethylbutylcarbamoyloxy, 1,1,2-trimethylpropylcarbamoyloxy, 1,2,2-trimethylpropylcarbamoyloxy, 15 1-ethyl-1-methylpropylcarbamoyloxy or 1-ethyl-2-methylpropylcarbamoyloxy, in particular methylcarbamoyloxy; (Ci-C 6 -haloalkyl)carbamoyloxy: a (Ci-C 6 -alkyl)carbamoyloxy 20 radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy, trichloromethylcarbamoyloxy, fluoromethylcarbamoyloxy, difluoromethylcarbamoyloxy, 25 trifluoromethylcarbamoyloxy, chlorofluoromethylcarbamoyloxy, dichlorofluoromethylcarbamoyloxy, chlorodifluoromethylcarbamoyloxy, 2-fluoroethylcarbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2,2-difluoroethylcarbamoyloxy, 30 2,2,2-trifluoroethylcarbamoyloxy, 2-chloro-2-fluoroethylcarbamoyloxy, 2-chloro-2,2-difluoroethylcarbamoyloxy, 2,2-dichloro-2-fluoroethylcarbamoyloxy, 2,2,2-trichloroethylcarbamoyloxy, 35 pentafluoroethylcarbamoyloxy, 2-fluoropropylcarbamoyloxy, 3-fluoropropylcarbamoyloxy, 2,2-difluoropropylcarbamoyloxy, 2,3-difluoropropylcarbamoyloxy, 2-chloropropylcarbamoyloxy, 3-chloropropylcarbamoyloxy, 2,3-dichloropropylcarbamoyloxy, 2-bromopropylcarbamoyloxy, 3-bromopropylcarbamoyloxy, 40 3,3,3-trifluoropropylcarbamoyloxy, 3,3,3-trichloropropylcarbamoyloxy, 2,2,3,3,3-pentafluoropropylcarbamoyloxy, heptafluoropropylcarbamoyloxy, 1-(fluoromethyl)-2-fluoroethylcarbamoyloxy, 45 1-(chloromethyl)-2-chloroethylcarbamoyloxy, 1-(bromomethyl)-2-bromoethylcarbamoyloxy, 4-fluorobutylcarbauoyloxy, 4-chlorobutylcarbamoyloxy, 21 4-bromobutylcarbamoyloxy or nonafluorobutylcarbamoyloxy, in particular trifluoromethylcarbamoyloxy; - Ci-C 6 -alkoxy: for example OCH 3 , OC 2
H
5 , OCH 2
-C
2
H
5 , OCH(CH 3
)
2 , 5 n-butoxy, OCH(CH 3
)-C
2
H
5 , OCH 2
-CH(CH
3
)
2 , OC(CH 3
)
3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 10 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 15 particular OCH 3 , OC 2
H
5 or OCH(CH 3
)
2 ; - Ci-C 4 -haloalkoxy: a Ci-C 4 -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 20 chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 25 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, 30 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, 35 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in particular 2-chloroethoxy or 2,2,2-trifluoroethoxy; - Ci-C 6 -haloalkoxy: a CI-C 6 -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, 40 chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under Ci-C 4 -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, 45 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy, in particular chloromethoxy, 22 fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy; - hydroxy-Ci-C 6 -alkoxy: for example OCH 2 -OH, OCH(CH 3 )-OH, 5 OCH 2
-CH
2 -OH, OCH(C 2
H
5 )-OH, OCH 2
-CH(CH
3 )-OH, 3-hydroxyprop-1-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, 10 4-hydroxybut-2-yloxy, 1-(CH 2 -OH)-eth-1-yloxy, 1-(CH 2 -OH)-1-(CH 3 )-eth-1-yloxy or 1-(CH 2 -OH)-prop-1-yloxy, in particular OCH 2 -OH or OCH 2
-CH
2 -OH; - cyano-Ci-C 6 -alkoxy: for example OCH 2 -CN, OCH(CH 3 )-CN, 15 OCH 2
-CH
2 -CN, OCH(C 2
H
5 )-OH, OCH 2
-CH(CH
3 )-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-(CH 2 -CN)-eth-1-yloxy, 1-(CH 2 -CN)-1-(CH 3 )-eth-1-yloxy or 20 1-(CH 2 -CN)-prop-1-yloxy, in particular OCH 2 -CN or OCH 2
-CH
2 -CN; - phenyl-Ci-C 6 -alkoxy: for example benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 25 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, 30 in particular benzyloxy or 2-phenylethoxy; - heterocyclyl-Ci-C 6 -alkoxy: for example heterocyclylmethoxy, 1-(heterocyclyl)ethoxy, 2-(heterocyclyl)ethoxy, 1-(heterocyclyl)prop-1-yloxy, 2-(heterocyclyl)prop-1-yloxy, 35 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, 40 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; 45 - phenyl-Ci-C 6 -alkylthio: for example benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-1-ylthio, 2-phenylpiup-1-ylthio, 3-phenylprop-1I-ylthio, 23 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, 5 1-(phenylmethyl)eth-1-ylthio, 1-(phenylmethyl)-1-(methyl)eth-1-ylthio or 1-(phenylmethyl)prop-1-ylthio, in particular benzylthio or 2-phenylethylthio; 10 - (Ci-C 6 -alkoxy)carbonyl: for example CO-OCH 3 , CO-OC 2
H
5 ,
COO-CH
2
-C
2
H
5 , CO-OCH(CH 3
)
2 , n-butoxycarbonyl, CO-OCH(CH 3
)-C
2
H
5 ,
CO-OCH
2
-CH(CH
3 )2, CO-OC(CH 3 )3, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 15 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 20 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 25 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular CO-OCH 3 ,
CO-OC
2
H
5 , CO-OCH(CH 3 )2 or CO-CH 2
-CH(CH
3 )2; (Ci-C 6 -alkoxy)carbonyloxy: methoxycarbonyloxy, 30 ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 35 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 40 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, 45 1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy or 1-ethy1-2-iniethylpLopoxycarbonylox, in partiualaz 24 methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy; - (Ci-C 6 -alkoxy)carbonylthio: methoxycarbonylthio, 5 ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1,1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio, 1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 10 3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio, 1,1-dimethylpropoxycarbonylthio, 1,2-dimethylpropoxycarbonylthio, 1-methylpentoxycarbonylthio, 2-methylpentoxycarbonylthio, 3-methylpentoxycarbonylthio, 15 4-methylpentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio, 2,3-dimethylbutoxycarbonylthio, 20 3,3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio, 1,1,2-trimethylpropoxycarbonylthio, 1,2,2-trimethylpropoxycarbonylthio, 1-ethyl 1-methylpropoxycarbonylthio or 25 1-ethyl-2-methylpropoxycarbonylthio, in particular methoxycarbonylthio, ethoxycarbonylthio or 1-methylethoxycarbonylthio; - Ci-C 6 -alkylthio: SCH 3 , SC 2
H
5 , SCH 2
-C
2
H
5 , SCH(CH 3
)
2 , 30 n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC(CH 3
)
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, 35 4-methylpentylthio, 1,1-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, 40 1-ethyl-1-methylpropylthio and 1-ethyl 2-methylpropylthio, in particular SCH 3 or SC 2
H
5 ; - Ci-C 6 -haloalkylthio: Ci-C 6 -alkylthio as mentioned above which is partially or fully substituted by fluorine, chlorine, 45 bromine and/or iodine, i.e., for example, SCHF 2 , SCF 3 , chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthLo, 25 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, SC 2
F
5 , 2-fluoropropylthio, 5 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, 10 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 15 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, in particular SCH 2 F, SCHF 2 , SCF 3 ,
SCH
2 Cl, 2-fluoroethylthio, 2-chloroethylthio or 2,2,2-trifluoroethylthio; 20 - Ci-C 6 -alkylsulfinyl: SO-CH 3 , SO-C 2
H
5 , n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 25 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 30 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 35 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, in particular SO-CH 3 ; Ci-C 6 -alkylsulfonyl: S0 2
-CH
3 , S0 2
-C
2
H
5 , n-propylsulfonyl, S0 2
-CH(CH
3 )2, n-butylsulfonyl, 1-methylpropylsulfonyl, 40 2-methylpropylsulfonyl, S0 2
-C(CH
3 )3, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 45 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1L-dimethylbutylsulfonyl, 1,2-dimtethy lbu yilulfonyl, 26 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 5 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, in particular S0 2
-CH
3 ;
CI-C
6 -alkylsulfonyloxy: O-SO 2
-CH
3 , O-SO 2
-C
2
H
5 , n-propylsulfonyloxy, O-SO 2
-CH(CH
3 )2, n-butylsulfonyloxy, 10 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy,
O-SO
2
-C(CH
3 )3, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1,1-dimethylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy, 15 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, 20 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 25 methylsulfonyloxy; Ci-C 6 -haloalkylsulfonyloxy: Ci-C 6 -alkylsulfonyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 30 ClCH 2
-SO
2 -0-, CH(Cl) 2
-SO
2 -0-, C(Cl) 3
-SO
2 -0-, FCH 2
-SO
2 -0-,
CHF
2 -SO2-0-, CF 3 -SO2-0-, chlorofluoromethyl-S0 2 -0-, dichlorofluoromethyl-S0 2 -0-, chlorodifluoromethyl-S0 2 -0-, 1-fluoroethyl-S0 2 -0-, 2-fluoroethyl-SO 2 -0-, 2-chloroethyl-SO 2 -0-, 2-bromoethyl-SO 2 -0-, 2-iodoethyl-SO 2 -0-, 35 2,2-difluoroethyl-SO 2 -0-, 2,2,2-trifluoroethyl-SO 2 -0-, 2-chloro-2-fluoroethyl-SO 2 -0-, 2-chloro-2,2-difluoroethyl-SO2-0-, 2,2-dichloro-2-fluoroethyl-SO 2 -0-, 2,2,2-trichloroethyl-SO 2 -0-, C 2
F
5
-SO
2 -0-, 40 2-fluoropropyl-SO 2 -0-, 3-fluoropropyl-SO 2 -0-, 2,2-difluoropropyl-SO 2 -0-, 2,3-difluoropropyl-SO 2 -0-, 2-chloropropyl-SO 2 -0-, 3-chloropropyl-SO 2 -0-, 2,3-dichloropropyl-SO 2 -0-, 2-bromopropyl-SO 2 -0-, 3-bromopropyl-SO 2 -0-, 3,3,3-trifluoropropyl-SO 2 -0-, 45 3,3,3-trichloropropyl-SO2-0-, 2,2,3,3,3-pentafluoropropyl-SO 2 -0-, C 2
F
5
-CF
2
-SO
2 -0-, i-(fluci-oomethyl)-2-fluoroethyl-SO 2 -0-, 27 1-(chloromethyl)-2-chloroethyl-SO 2 -0-, 1-(bromomethyl)-2-bromoethyl-SO 2 -0-, 4-fluorobutyl-SO 2 -0-, 4-chlorobutyl-SO2-0-, 4-bromobutyl-SO2-0-,
C
2
F
5
-CF
2
-CF
2
-SO
2 -0-, 5-fluoropentyl-SO 2 -0-, 5-chloropentyl-SO 2 -0-, 5 5-bromopentyl-SO2-0-, 5-iodopentyl-SO2-0-, 5,5,5-trichloropentyl-SO 2 -0-, C 2
F
5
-CF
2
-CF
2
-CF
2
-SO
2 -0-, 6-fluorohexyl-SO2-0-, 6-chlorohexyl-SO2-0-, 6-bromohexyl-SO 2 -0-, 6-iodohexyl-SO2-0-, 6,6,6-trichlorohexyl-SO 2 -0- or dodecafluorohexyl-S0 2 -0-, in 10 particular CF 3
-SO
2 -0-; (Ci-C 6 -alkyl)aminocarbonyl: (Ci-C 4 -alkyl)aminocarbonyl as mentioned above and also for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 15 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 20 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 25 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 30 1-ethyl-2-methylpropylaminocarbonyl, in particular CO-NH-CH 3 ,
CO-NH-C
2
H
5 or CO-NH-CH(CH 3
)
2 ; di(Ci-C 6 -alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, 35 N,N-dipropylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N, N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, 40 N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, 45 N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propy lamiinocarbonyl, 28 N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, 5 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, 10 N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, 15 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 20 N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in particular N,N-dimethylaminocarbonyl or N,N-diethylaminocarbonyl; (Ci-C 6 -alkyl)iminooxycarbonyl: methyliminooxycarbonyl, 25 ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methylethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methylpropyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1,1-dimethylethyliminooxycarbonyl, n-pentyliminooxycarbonyl, 30 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1,1-dimethylpropyliminooxycarbonyl, 1,2-dimethylpropyliminooxycarbonyl, 2,2-dimethylpropyliminooxycarbonyl, 35 1-ethylpropyliminooxycarbonyl, n-hexyliminooxycarbonyl, 1-methylpentyliminooxycarbonyl, 2-methylpentyliminooxycarbonyl, 3-methylpentyliminooxycarbonyl, 4-methylpentyliminooxycarbonyl, 40 1,1-dimethylbutyliminooxycarbonyl, 1,2-dimethylbutyliminooxycarbonyl, 1,3-dimethylbutyliminooxycarbonyl, 2,2-dimethylbutyliminooxycarbonyl, 2,3-dimethylbutyliminooxycarbonyl, 45 3,3-dimethylbutyliminooxycarbonyl, 1-ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl, 1,1,2-trimethylpropyliminooxycdrbjnyl, 29 1,2,2-trimethylpropyliminooxycarbonyl, 1-ethyl-1-methylpropyliminooxycarbonyl or 1-ethyl-2-methylpropyliminooxycarbonyl, in particular methyliminooxycarbonyl, ethyliminooxycarbonyl or 5 1-methylethyliminooxycarbonyl; Ci-C 6 -alkylideneaminooxy: 1-propylideneaminooxy, 2-propylideneaminooxy, 1-butylideneaminooxy, 2-butylideneaminooxy or 2-hexylideneaminooxy, in particular 10 acetylideneaminooxy or 2-propylideneaminooxy; - Ci-C 6 -alkyliminooxy: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, 15 n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyliminooxy, in particular methyliminooxy, ethyliminooxy or 1-methylethyliminooxy; 20 - Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)aminocarbonyl: (Ci-C 6 -alkyl)aminocarbonyl such as CO-NH-CH 3 , CO-NH-C 2
H
5 ,
CO-NH-CH
2
-C
2
H
5 , CO-NH-CH(CH 3 )2, CO-NH-(CH 2
)
3
-CH
3 ,
CO-NH-CH(CH
3
)-C
2
H
5 , CO-NH-CH 2
-CH(CH
3 )2, CO-NH-C(CH 3 )3,
CO-NH-(CH
2
)
4
-CH
3 , 1-methylbutylaminocarbonyl, 25 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 30 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 35 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl and 40 1-ethyl-2-methylpropylaminocarbonyl, preferably (Ci-C 4 -alkyl)aminocarbonyl, which is substituted by Ci-C 6 -alkoxy as mentioned above, i.e., for example,
CO-NH-CH
2
-OCH
3 or CO-NH-CH 2
-OC
2
H
5 ; 45 - Ci-C 6 -alkoxyamino-Ci-C 6 -alkyl: for example CH 2
-NH-OCH
3 ,
CH
2
-NH-OC
2
H
5 , CH 2
-NH-OCH
2
-C
2
H
5 , CH 2
-NH-OCH(CH
3 )2,
CH
2 -NH-u%,CH 2
-CH
2
-C
2
H
5 , CH 2 -Nh-OCH(CH3)-C 2
H
5
,
30
CH
2
-NH-OCH
2
-CH(CH
3 )2, CH 2
-NH-OC(CH
3 )3, CH 2
-NH-OCH
2
-(CH
2
)
3
-CH
3 , (1-methylbutoxyamino)methyl, (2-methylbutoxyamino)methyl, (3-methylbutoxyamino)methyl, (2,2-dimethylpropoxyamino)methyl, 5 (1-ethylpropoxyamino)methyl, n-hexoxyaminomethyl, (1,1-dimethylpropoxyamino)methyl, (1,2-dimethylpropoxyamino)methyl, (1-methylpentoxyamino)methyl, (2-methylpentoxyamino)methyl, (3-methylpentoxyamino)methyli (4-methylpentoxyamino)methyl, 10 (1,1-dimethylbutoxyamino)methyl, (1,2-dimethylbutoxyamino)methyl, (1,3-dimethylbutoxyamino)methyl, (2,2-dimethylbutoxyamino)methyl, (2,3-dimethylbutoxyamino)methyl, 15 (3,3-dimethylbutoxyamino)methyl, (1-ethylbutoxyamino)methyl, (2-ethylbutoxyamino)methyl, (1,1,2-trimethylpropoxyamino)methyl, (1,2,2-trimethylpropoxyamino)methyl, (1-ethyl-1-methylpropoxyamino)methyl, 20 (1-ethyl-2-methylpropoxyamino)methyl, methoxyaminoethyl, ethoxyaminoethyl, n-propoxyaminoethyl, (1-methylethoxyamino)ethyl, n-butoxyaminoethyl, (1-methylpropoxyamino)ethyl, (2-methylpropoxyamino)ethyl, (1,1-dimethylethoxyamino)ethyl, n-pentoxyaminoethyl, 25 (1-methylbutoxyamino)ethyl, (2-methylbutoxyamino)ethyl, (3-methylbutoxyamino)ethyl, (2,2-dimethylpropoxyamino)ethyl, (1-ethylpropoxyamino)ethyl, n-hexoxyaminoethyl, (1,1-dimethylpropoxyamino)ethyl, (1,2-dimethylpropoxyamino)ethyl, (1-methylpentoxyamino)ethyl, 30 (2-methylpentoxyamino)ethyl, (3-methylpentoxyamino)ethyl, (4-methylpentoxyamino)ethyl, (1,1-dimethylbutoxyamino)ethyl, (1,2-dimethylbutoxyamino)ethyl, (1,3-dimethylbutoxyamino)ethyl, (2,2-dimethylbutoxyamino)ethyl, 35 (2,3-dimethylbutoxyamino)ethyl, (3,3-dimethylbutoxyamino)ethyl, (1-ethylbutoxyamino)ethyl, (2-ethylbutoxyamino)ethyl, (1,1,2-trimethylpropoxyamino)ethyl, (1,2,2-trimethylpropoxyamino)ethyl, 40 (1-ethyl-1-methylpropoxyamino)ethyl, (1-ethyl-2-methylpropoxyamino)ethyl, 2-(methoxyamino)propyl, 3-(methoxyamino)propyl or 2-(ethoxyamino)propyl, preferably Ci-C 6 -alkoxyamino-Ci-C 2 -alkyl; 45 - Ci-C 6 -alkoxy-Ci-C 6 -alkylamino-Ci-C 6 -alkyl: Ci-C 6 -alkylamino-Ci-C 6 -alkyl, such as CH 2
-NH-CH
3 , CH 2
-NH-G
2
H
5 ,
CH
2
-NH-CH
2
-C
2
H
5 , CH 2
-NH-CH(CH
3 )2, CH 2
-NH-(CH
2
)
3
-CH
3
,
31
CH
2
-NH-CH(CH
3
)-C
2
H
5 , CH 2
-NH-CH
2
-CH(CH
3 )2, CH 2
-NH-C(CH
3 )3,
CH
2
-NH-(CH
2
)
4
-CH
3 , (1-methylbutylamino)methyl, (2-methylbutylamino)methyl, (3-methylbutylamino)methyl, (2,2-dimethylpropylamino)methyl, (1-ethylpropylamino)methyl, 5 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, 10 (1,3-dimethylbutylamino)methyl, (2,2-dimethylbutylamino)methyl, (2,3-dimethylbutylamino)methyl, (3,3-dimethylbutylamino)methyl, (1-ethylbutylamino)methyl, (2-ethylbutylamino)methyl, 15 (1,1,2-trimethylpropylamino)methyl, (1,2,2-trimethylpropylamino)methyl, (1-ethyl-1-methylpropylamino)methyl, (1-ethyl-2-methylpropylamino)methyl, methylaminoethyl, ethylaminoethyl, n-propylaminoethyl, 20 (1-methylethylamino)ethyl, n-butylaminoethyl, (1-methylpropylamino)ethyl, (2-methylpropylamino)ethyl, (1,1-dimethylethylamino)ethyl, n-pentylaminoethyl, (1-methylbutylamino)ethyl, (2-methylbutylamino)ethyl, (3-methylbutylamino)ethyl, (2,2-dimethylpropylamino)ethyl, 25 (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, 30 (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-trimethylpropylamino)ethyl, (1,2,2-trimethylpropylamino)ethyl, 35 (1-ethyl-1-methylpropylamino)ethyl, (1-ethyl-2-methylpropylamino)ethyl, 2-(methylamino)propyl, 3-(methylamino)propyl and 2-(ethylamino)propyl, preferably Ci-C 6 -alkylamino-Ci-C 2 -alkyl, which is substituted by Ci-C 6 -alkoxy as mentioned above, i.e., for example, 40 CH 2
-NH-CH
2
-OCH
3 or CH 2
-NH-CH
2
-OC
2
H
5 ; Ci-C 6 -alkyloximino-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by Ci-C 6 -alkyloximino, such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxyimino, 45 1-methylethoxyimino, n-butoxyimino, sec-butoxyimino, tert-butoxyimino, 1-methyl-1-propoxyimino, 2-methyI-1-propoAyiminno, I-methyl-2-propoxyimino, 32 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, 5 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, 10 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino, 1-methyl-1-pentoxyimino, 2-methyl-1-pentoxyimino, 3-methyl-1-pentoxyimino, 4-methyl-1-pentoxyimino, 1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino, 3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino, 15 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, 20 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, 25 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, 30 1-ethyl-1-methyl-2-propoxyimino, 1-ethyl-2-methyl-1-propoxyimino and 1-ethyl-2-methyl-2-propoxyimino, i.e., for example, methoxyiminomethyl; 35 - Ci-C 6 -alkoxy-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by Ci-C 6 -alkoxy as mentioned above, i.e., for example, CH 2
-OCH
3 ,
CH
2
-OC
2
H
5 , n-propoxymethyl,
CH
2
-OCH(CH
3 )2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl,
CH
2
-OC(CH
3
)
3 , 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 40 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, 45 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, .-(ethoxy)propyl, 3-(n-propoxy)propyl, 33 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, 5 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, 10 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, in particular CH 2
-OCH
3 or 2-methoxyethyl; 15 - di(Ci-C 6 -alkoxy)-Ci-C 6 -alkyl: for example 2,2-dimethoxyethyl or 2,2-diethoxyethyl; - Ci-C 6 -alkoxy-Ci-C 6 -alkoxy: Ci-C 6 -alkoxy which is substituted 20 by Ci-C 6 -alkoxy as mentioned above, i.e., for example,
OCH
2
-OCH
3 , OCH 2
-OC
2
H
5 , n-propoxymethoxy, OCH 2
-OCH(CH
3 )2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH 2
-OC(CH
3 )3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 25 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, 30 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, 35 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, 40 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, 45 4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy, 4-(1,1i-dinetiylethoxy)butoxy, 5-(methuxy)pentoxy, 34 5-(ethoxy)pentoxy, 5-(n-propoxy)pentoxy, 5-(1-methylethoxy)pentoxy, 5-(n-butoxy)pentoxy, 5-(1-methylpropoxy)pentoxy, 5-(2-methylpropoxy)pentoxy, 5-(1,1-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy, 5 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 OCH 2
-OCH
3 or
OCH
2
-OC
2
H
5 ; 10 - (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkoxy: Ci-C 6 -alkoxy which is substituted by (Ci-C 6 -alkyl)carbonyl as mentioned above, i.e., for example, OCH 2
-CO-CH
3 , OCH 2
-CO-C
2
H
5 , OCH 2
-CO-CH
2
-C
2
H
5
OCH
2
-CO-CH(CH
3
)
2 , n-butylcarbonyl-methoxy, 1-(CO-CH 3 )ethoxy, 15 2-(CO-CH 3 )ethoxy, 2-(CO-C 2
H
5 )ethoxy, 2-(CO-CH 2
-C
2
H
5 )ethoxy, 2-(n-butylcarbonyl)ethoxy, 3-(CO-CH 3 )propoxy, 3-(CO-C 2
H
5 )-propoxy, 3-(CO-CH 2
-C
2
H
5 )propoxy, 3-(n-butylcarbonyl)propoxy, 4-(CO-CH 3 )butoxy, 4-(CO-C 2
H
5 )butoxy, 4-(CO-CH 2
-C
2
H
5 )butoxy, 20 4-(n-butylcarbonyl)butoxy, 5-(CO-CH 3 )pentoxy, 5-(CO-C 2
H
5 )pentoxy, 5-(CO-CH 2
-C
2
H
5 )pentoxy, 5-(n-butylcarbonyl)butoxy, 6-(CO-CH 3 )hexoxy, 6-(CO-C 2
H
5 )hexoxy, 6-(CO-CH 2
-C
2
H
5 )hexoxy or 6-(n-butylcarbonyl)hexoxy, in particular OCH 2
-CO-OCH
3 or 25 1-(CO-CH 3 )ethoxy; - (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkoxy: Ci-C 6 -alkoxy which is substituted by (Ci-C 6 -alkoxy)carbonyl as mentioned above, i.e., for example, OCH 2
-CO-OCH
3 , OCH 2
-CO-OC
2
H
5 , 30 OCH 2
-CO-OCH
2
-C
2
H
5 , OCH 2
-CO-OCH(CH
3 )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, 35 3-(n-butoxycarbonyl)propoxy, 4-(methoxycarbonyl)butoxy, 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, 40 6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or 6-(n-butoxycarbonyl)hexoxy, in particular OCH 2
-CO-OCH
3 or 1-(methoxycarbonyl)ethoxy; - (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is 45 substituted by (Ci-C 6 -alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethyl, -ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 35 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl; 5 - (Ci-C6-alkoxy)carbonyl-Cl-C 6 -alkylsulfonyl: Ci-C 6 -alkylsulfonyl which is substituted by (Ci-C 6 -alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1-(methoxycarbonyl)ethylsulfonyl, 10 2-(methoxycarbonyl)ethylsulfonyl, 2-(ethoxycarbonyl)ethylsulfonyl, 3-(methoxycarbonyl)propylsulfonyl, 4-(methoxycarbonyl)butylsulfonyl, 5-(methoxycarbonyl)pentylsulfonyl or 15 6-(methoxycarbonyl)hexylsulfonyl;. - Ci-C 6 -alkylthio-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by Ci-C 6 -alkylthio as mentioned above, i.e., for example,
CH
2
-SCH
3 , CH 2
-SC
2
H
5 , CH 2
-SCH
2
-C
2
H
5 , CH 2
-SCH(CH
3 )2, 20 n-butylthiomethyl,
CH
2
-SCH(CH
3
)-C
2
H
5 , CH 2
-SCH
2
-CH(CH
3 )2,
CH
2
-SC(CH
3
)
3 , 2-(SCH 3 )ethyl, 2-(SC 2
H
5 )ethyl, 2-(SCH 2
-C
2
H
5 )ethyl, 2-[SCH(CH 3
)
2 ]ethyl, 2-(n-butylthio)ethyl, 2-[SCH(CH 3
)-C
2
H
5 ]ethyl, 2-(2-methylpropylthio)ethyl, 2-[SC(CH 3
)
3 ]ethyl, 2-(SCH 3 )propyl, 3-(SCH 3 )propyl, 25 2-(SC 2
H
5 )propyl, 3-(SC 2
H
5 )propyl, 3-(SCH2-C 2
H
5 )propyl, 3-(butylthio)propyl, 4-(SCH 3 )butyl, 4-(SC 2
H
5 )butyl, 4-(SCH 2
-C
2
H
5 )butyl or 4-(n-butylthio)butyl, in particular 2-(SCH 3 )ethyl; 30 - Ci-C6-alkylthio-Ci-C 6 -alkoxy: Ci-C 6 -alkoxy which is substituted by Ci-C 6 -alkylthio as mentioned above, i.e., for example, OCH 2
-SCH
3 , OCH 2
-SC
2
H
5 , OCH 2
-SCH
2
-C
2
H
5 , OCH 2
-SCH(CH
3 ) 2r n-butylthiomethoxy,
OCH
2
-SCH(CH
3
)-C
2
H
5 , OCH 2
-SCH
2
-CH(CH
3 )2,
OCH
2
-SC(CH
3
)
3 , 2-(SCH 3 )ethoxy, 2-(SC 2
H
5 )ethoxy, 35 2-(SCH 2
-C
2
H
5 )ethoxy, 2-[SCH(CH 3
)
2 ]ethoxy, 2-(n-butylthio)ethoxy, 2-[SCH(CH 3
)-C
2
H
5 ]ethoxy, 2-(2-methylpropylthio)ethoxy, 2-[SC(CH 3 )3]ethoxy, 2-(SCH 3 )propoxy, 3-(SCH 3 )propoxy, 2-(SC2H 5 )propoxy, 3-(SC 2
H
5 )propoxy, 3-(SCH 2
-C
2
H
5 )propoxy, 3-(butylthio)propoxy, 40 4-(SCH 3 )butoxy, 4-(SC 2
H
5 )butoxy, 4-(CH2-C 2
H
5 )butoxy or 4-(n-butylthio)butoxy, in particular 2-(SCH 3 )ethoxy; - Ci-C6-alkylthio-(Cl-C 6 -alkyl)carbonyl: (Ci-C6-alkyl)carbonyl which is substituted by Ci-C 6 -alkylthio as mentioned above, 45 preferably by SCH 3 or SC 2
H
5 , i.e., for example, methylthiomethylcarbonyl, ethylthiomethylcarbonyl, 1-(methylthiogethylcarbouyl, 2- 1 metiylthio)ethylcarbonyl, 36 3-(methylthio)propylcarbonyl, 4-(methylthio)butylcarbonyl, 5-(methylthio)pentylcarbonyl or 6-(methylthio)hexylcarbonyl, in particular CO-CH 2
-SCH
3 or CO-CH(CH 3
)-SCH
3 ; 5 - di(Ci-C 6 -alkyl)amino-Ci-C 6 -alkoxy: Ci-C 6 -alkoxy which is substituted by di(Ci-C 6 -alkyl)amino, such as N(CH 3
)
2 , N(C 2
H
5
)
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(CH
3
)
3
]
2 , 10 N-ethyl-N-methylamino, N-methyl-N-propylAtino, 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, 15 N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethyidmnino, 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, 20 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, 25 N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, 30 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,
OCH
2
-N(CH
3
)
2 , OCH 2
-N(C
2
H
5
)
2 , OCH(CH 3
)-N(CH
3
)
2 , 35 2-(dimethylamino)ethoxy,
OCH(CH
3
)-N(C
2
H
5
)
2 , 3-(dimethylamino)propoxy, 4-(dimethylamino)butoxy, 5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in particular OCH 2
-N(CH
3
)
2 or OCH(CH 3
)-N(CH
3
)
2 ; 40 - C 3
-C
6 -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, 45 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-ei-1-yl, 37 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, 5 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, 10 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; 15 - C 3
-C
6 -haloalkenyl: C 3
-C
6 -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, 20 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; 25 - C 2
-C
6 -alkenyl: ethenyl or one of the radicals mentioned under
C
3
-C
6 -alkenyl, in particular ethenyl or prop-2-en-1-yl; - C 3
-C
6 -alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 30 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, 35 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, 40 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, 45 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-awethy lpeut-2-eix-1-yloxy , 4-methylpent-2-=fn-1-yloxy
,
38 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, 5 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, 10 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-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, 15 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; 20
C
2
-C
6 -alkenyloxy: ethenyloxy or one of the radicals mentioned under C 3
-C
6 -alkenyloxy, in particular ethenyloxy or prop-2-en-1-yloxy; 25 - C 3
-C
6 -haloalkenyloxy: C 3
-C
6 -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, 30 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; 35 - phenyl-C 3
-C
6 -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; 40 - heterocyclyl-C 3
-C
6 -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 45 3-heterocyclylallyloxy; 39
C
2
-C
6 -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, 5 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-l-en-1-ylthio, 1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio, 10 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-dimethylprop-2-en-1-ylthio, 1,2 -dimethyiprop- 1-en-i -ylthio, 1, 2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio, 15 1-ethylprop-2-en-1-ylthio, n-hex-l-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-methyltpent-l-en-1-ylthio, 4-methylpent-l-en-1-ylthio, 20 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, 25 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, 30 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, 35 2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio, 1,1, 2-trimethylprop-2-en-1-ylthio, I-ethyl-1-methylprop-2-en-1-ylthio, I-ethyl-2-methylprop-1-en-1-ylthio or 1-ethyl-2-methylprop-2-en-1-ylthio, in particular ethenylthio 40 or prop-2-en-1-ylthio;
C
3
-C
6 -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-1-yn-3-yl, 45 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-yi, i-iex-i-yi-i-yl, a-hex-1-yn-3-yl, 40 n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 5 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; - C 2
-C
6 -alkynyl: ethynyl or one of the radicals mentioned under 10 C 3
-C
6 -alkynyl, in particular ethynyl or prop-2-yn-1-yl; - C 3
-C
6 -alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy, 15 n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-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, 20 n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy, 25 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy, in particular prop-2-yn-1-yloxy; - C 2
-C
6 -alkynyloxy: ethynyloxy or one of the radicals mentioned under C 3
-C
6 -alkynyloxy, in particular ethynyloxy or 30 prop-2-yn-1-yloxy; - phenyl-C 3
-C
6 -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 35 6-phenylhex-4-yn-1-yloxy, in particular 3-phenylprop-2-yn-1-yloxy or 3-phenylbut-3-yn-2-yloxy; - heterocyclyl-C 3
-C
6 -alkynyloxy: for example 3-(heterocyclyl)prop-2-yn-1-yloxy, 40 4-(heterocyclyl)but-2-yn-1-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 45 3-yn-2-yloxy; 41 - C 3
-C
6 -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, 5 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, 10 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, 15 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; - C 2
-C
6 -alkynylthio: ethynylthio or one of the radicals 20 mentioned under C 3
-C
6 -alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio; - (C 3
-C
6 -alkenyloxy)carbonyl: prop-l-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl, 25 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, 30 n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-yloxycarbonyl, 2-methylbut-l-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl, 1-methylbut-2-en-1-yloxycarbonyl, 35 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, 40 1,1-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-l-en-1-yloxycarbonyl, 45 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--en-1-yloxycarbonyl, 42 2-methylpent-1-en-1-yloxycarbonyl, 3-methylpent-1-en-1-yloxycarbonyl, 4-methylpent-l-en-1-yloxycarbonyl, 1-methylpent-2-en-1-yloxycarbonyl, 5 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, 10 3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-1-yloxycarbonyl, 1-methylpent-4-en-1-yloxycarbonyl, 2-methylpent-4-en-1-yloxycarbonyl, 3-methylpent-4-en-1-yloxycarbonyl, 15 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, 20 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, 25 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, 30 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, 35 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 40 prop-2-en-1-yloxycarbonyl;
(C
3
-C
6 -alkenyloxy)carbonyl-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by (C 3
-C
6 -alkenyloxy)carbonyl as mentioned above, preferably by prop-2-en-1-yl-oxycarbonyl, i.e., for example, 45 prop-2-en-1-yl-oxycarbonylmethyl; 43
(C
2
-C
6 -alkenyl )carbonyloxy: ethenylcarbonyloxy, prop-1-en-i-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy, 1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 5 1-methylprop-1-en-1-ylcarbonyloxy, 2 -iethyiprop- 1-en-i -ylcarbonyloxy, 1-methylprop-2 -en-1-ylcarbonyloxy, 2-methylprop-2-en-i-ylcarbonyloxy, n-penten-i-ylcarbonyloxy, n-penten-2 -ylcarbonyloxy, n-penten-3 -ylcarbonyloxy, 10 n-penten-4-ylcarbonyloxy, 1-methylbut-i-en-i-ylcarbonyloxy, 2 -methylbut- 1-en-i -ylcarbonyloxy, 3 -methylbut- 1-en- 1-ylcarbonyloxy, 1 -methylbut-2 -en-i -ylcarbonyloxy, 2 -methylbut-2-en- 1-ylcarbonyloxy, 15 3-methylbut-2-en-i-ylcarbonyloxy, 1 -methylbut-3-en- 1-ylcarbonyloxy, 2 -methylbut-3-en- i-ylcarbonyloxy, 3 -methylbut-3 -en- i-ylcarbonyloxy, 1 ,i-dimethylprop-2-en-i-ylcarbonyloxy, 20 1, 2-dixethylprop-i-en-i-ylcarbonyloxy, 1 ,2-dimethylprop-2-en-i-ylcarbonyloxy, I-ethylprop-i-en-2 -ylcarbonyloxy, I-ethylprop-2-en-i-ylcarbonyloxy, n-hex-i-en-i-ylcarbonyloxy, n-hex-2-en-i-ylcarbonyloxy, n-hex-3-en-i-ylcarbonyloxy, 25 n-hex-4-en-i-ylcarbonyloxy, n-hex-5-en-i-ylcarbonyloxy, i-methylpent-i-en-i-ylcarbonyloxy, 2 -methylpent- i-en- i-ylcarbonyloxy, 3 -methylpent- i-en-i -ylcarbonyloxy, 4 -methylpent- i-en-i -ylcarbonyloxy, 30 i-methylpent-2-en-1-ylcarbonyloxy, 2 -methylpent-2 -en-i -ylcarbonyloxy, 3 -methylpent-2 -en-i -ylcarbonyloxy, 4 -methylpent-2 -en-i -ylcarbonyloxy, i-methylpent-3 -en-i -ylcarbonyloxy, 35 2-methylpent-3-en-i-ylcarbonyloxy, 3 -methylpent-3 -en-i -ylcarbonyloxy, 4-methylpent-3 -en-i-ylcarbonyloxy, i-methylpent-4 -en-i-ylcarbonyloxy, 2 -methylpent-4 -en- i-ylcarbonyloxy, 40 3-methylpent-4-en-1-ylcarbonyloxy, 4 -methylpent-4 -en- i-ylcarbonyloxy, 1 ,i-dimethylbut-2-en-i-ylcarbonyloxy, 1 ,i-dimethylbut-3-en-i-ylcarbonyloxy, 1,2 -dimethylbut- i-en-i -ylcarbonyloxy, 45 1 ,2-dimethylbut-2-en-1-ylcarbonyloxy, 1, 2-dimethylbut-3-en-i-ylcarbonyloxy, - 1 ,3-dimethylbiut-i-en-i-ylcrbony~oxy, 44 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, 5 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, 10 1-ethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-3-en-1-ylcarbonyloxy, 2-ethylbut-1-en-1-ylcarbonyloxy, 2-ethylbut-2-en-1-ylcarbonyloxy, 2-ethylbut-3-en-1-ylcarbonyloxy, 15 1,1,2-trimethylprop-2-en-1-ylcarbonyloxy, 1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy, 1-ethyl-2-methylprop-i-en-1-ylcarbonyloxy or 1-ethyl-2-methylprop-2-en-1-ylcarbonyloxy, in particular ethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy; 20 - (C 2
-C
6 -alkenyl)carbonylthio: ethenylcarbonylthio, prop-i-en-1-ylcarbonylthio, prop-2-en-1-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-buten-2-ylcarbonylthio, n-buten-3-ylcarbonylthio, 25 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, 30 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, 35 2-methylbut-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, 40 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, I-ethylprop-2-en-1-ylcarbonylthio, 45 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-'-e-1-ylcarbonylthio, 45 1-methylpent-1-en-1-ylcarbonylthio, 2-methylpent-1-en-1-ylcarbonylthio, 3-methylpent-1-en-1-ylcarbonylthio, 4-methylpent-1-en-1-ylcarbonylthio, 5 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, 10 2-methylpent-3-en-1-ylcarbonylthio, 3-methylpent-3-en-1-ylcarbonylthio, 4-methylpent-3-en-1-ylcarbonylthio, 1-methylpent-4-en-1-ylcarbonylthio, 2-methylpent-4-en-1-ylcarbonylthio, 15 3-methylpent-4-en-1-ylcarbonylthio, 4-methylpent-4-en-1-ylcarbonylthio, 1,1-dimethylbut-2-en-1-ylcarbonylthio, 1,1-dimethylbut-3-en-1-ylcarbonylthio, 1,2-dimethylbut-1-en-1-ylcarbonylthio, 20 1,2-dimethylbut-2-en-1-ylcarbonylthio, 1,2-dimethylbut-3-en-1-ylcarbonylthio, 1,3-dimethylbut-1-en-1-ylcarbonylthio, 1,3-dimethylbut-2-en-1-ylcarbonylthio, 1,3-dimethylbut-3-en-1-ylcarbonylthio, 25 2,2-dimethylbut-3-en-1-ylcarbonylthio, 2,3-dimethylbut-1-en-1-ylcarbonylthio, 2,3-dimethylbut-2-en-1-ylcarbonylthio, 2,3-dimethylbut-3-en-1-ylcarbonylthio, 3,3-dimethylbut-1-en-1-ylcarbonylthio, 30 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, 2-ethylbut-1-en-1-ylcarbonylthio, 2-ethylbut-2-en-1-ylcarbonylthio, 35 2-ethylbut-3-en-1-ylcarbonylthio, 1,1,2-trimethylprop-2-en-1-ylcarbonylthio, 1-ethyl-1-methylprop-2-en-1-ylcarbonylthio, I-ethyl-2-methylprop-1-en-1-ylcarbonylthio or I-ethyl-2-methylprop-2-en-1-ylcarbonylthio, in particular 40 ethenylcarbonylthio or prop-2-en-1-ylcarbonylthio;
(C
2
-C
6 -alkynyl)carbonyloxy: ethynylcarbonyloxy, prop-1-yn-1-ylcarbonyloxy, prop-2-yn-1-ylcarbonyloxy, n-but-1-yn-1-ylcarbonyloxy, n-but-1-yn-3-ylcarbonyloxy, 45 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-ylcarbunylovxy, n-pent-1-yn-5-ylcarbony loxy-, 46 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, 5 n-hex-1-yn-3-ylcarbonyloxy, n-hex-1-yn-4-ylcarbonyloxy, n-hex-1-yn-5-ylcarbonyloxy, n-hex-1-yn-6-ylcarbonyloxy, n-hex-2-yn-1-ylcarbonyloxy, n-hex-2-yn-4-ylcarbonyloxy, n-hex-2-yn-5-ylcarbonyloxy, n-hex-2-yn-6-ylcarbonyloxy, n-hex-3-yn-1-ylcarbonyloxy, n-hex-3-yn-2-ylcarbonyloxy, 10 3-methylpent-1-yn-1-ylcarbonyloxy, 3-methylpent-1-yn-3-ylcarbonyloxy, 3-methylpent-1-yn-4-ylcarbonyloxy, 3-methylpent-1-yn-5-ylcarbonyloxy, 4-methylpent-1-yn-1-ylcarbonyloxy, 15 4-methylpent-2-yn-4-ylcarbonyloxy or 4-methylpent-2-yn-5-ylcarbonyloxy, in particular ethynylcarbonyloxy or prop-2-yn-1-ylcarbonyloxy;
C
3
-C
6 -alkynylsulfonyloxy: prop-1-yn-1-ylsulfonyloxy, 20 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, 25 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, 30 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, 35 3-methylpent-1-yn-4-ylsulfonyloxy, 3-methylpent-1-yn-5-ylsulfonyloxy, 4-methylpent-1-yn-1-ylsulfonyloxy, 4-methylpent-2-yn-4-ylsulfonyloxy or 4-methylpent-2-yn-5-ylsulfonyloxy, in particular 40 prop-2-yn-1-ylsulfonyloxy;
(C
2
-C
6 -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, 45 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, 47 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, 5 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, 10 n-hex-3-yn-2-ylcarbonylthio, 3-methylpent-1-yn-1-ylcarbonylthio, 3-methylpent-1-yn-3-ylcarbonylthio, 3-methylpent-1-yn-4-ylcarbonylthio, 3-methylpent-1-yn-5-ylcarbonylthio, 15 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; 20 - (Ci-C 6 -alkoxy)carbonyl-C 2
-C
6 -alkenyl: C 2
-C
6 -alkenyl which is substituted by (Ci-C 6 -alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylprop-2-en-1-yl; - (Ci-C6-alkoxy)carbonyl-C 2
-C
6 -alkenyloxy: C 2
-C
6 -alkenyloxy 25 which is substituted by (Ci-C 6 -alkoxy)carbonyl as mentioned above, i.e., for example, 1-methoxycarbonylethen-1-yloxy and methoxycarbonylprop-2-en-1-yloxy; - Ci-C 6 -alkoxy-C 3
-C
6 -alkenyloxy: C 3
-C
6 -alkenyloxy which is 30 substituted by Ci-C 6 -alkoxy as mentioned above, i.e., for example, methylprop-2-en-1-yloxy; - C 3
-C
6 -alkenyloxy-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted by C 3
-C
6 -alkenyloxy as mentioned above, preferably allyloxy, 35 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; - C 3
-C
6 -alkynyloxy-Ci-C 6 -alkyl: Ci-C 6 -alkyl which is substituted 40 by C 3
-C
6 -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; 45 - C 3
-C
6 -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; 48 - C 3
-C
6 -cycloalkyl-Ci-C 6 -alkoxy: for example cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1-(cyclopropyl)ethoxy, 1-(cyclobutyl)ethoxy, 1-(cyclopentyl)ethoxy, 1-(cyclohexyl)ethoxy, 5 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, 10 4-(cyclopentyl)butoxy, 4-(cyclohexyl)butoxy, 5-(cyclopropyl)pentoxy, 5-(cyclobutyl)pentoxy, 5-(cyclopentyl)pentoxy, 5-(cyclohexyl)pentoxy, 6-(cyclopropyl)hexoxy, 6-(cyclobutyl)hexoxy, 6-(cyclopentyl)hexoxy or 6-(cyclohexyl)hexoxy, in particular 15 cyclopentylmethoxy or cyclohexylmethoxy; - C 3
-C
6 -cycloalkyloxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy; 20 - C 3
-C
6 -cycloalkylthio: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio; - C 3
-C
6 -cyCloalkylcarbonyloxy: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or 25 cyclohexylcarbonyloxy; - C 3
-C
6 -cycloalkylsulfonyloxy: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy; 30 - C 5
-C
7 -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 35 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, 40 isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and azepin-1-yl. 45 49 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 5 heteroatoms selected from a group consisting of - one to three nitrogen atoms, - one or two oxygen atoms and - one or two sulfur atoms. 10 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, 15 azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 20 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, 25 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, 30 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, 35 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, 40 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, 45 hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, 50 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 5 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 10 and 6 members, i.e., for example furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, 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 15 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, oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl 20 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 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as 25 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. 30 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: 35 Z is O or S RA is C0 2
R
1 , halogen, cyano, OR 2 or Ci-C 3 -alkyl; Q is Q1, 02 or Q4; 40 X, Y and Y' independently of one another are 0 or S; T is a chemical bond or 0; 45 U is a chemical bond, CI-C 4 -alkylene, 0 or S; 51 R is hydrogen, C(O)OR 1 0 , C(O)SR 1 0 , C(S)OR 1 0 , C(S)SR 1 0, CHO, CN, C(O)R 2 , C(O)NR 1 1
R
12 , C(S)NR 1 1
R
1 2 , C(O)NHC(O)OR 1 2 ',
C(O)NHS(O)
2
R
1 2 ', C(O)NHS(O) 2
OR
1 2 '; 5 R 1 is hydrogen or Ci-C 3 -alkyl;
R
2 is Ci-C 3 -alkyl, C 3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, Ci-C 3 -haloalkyl, Ci-C 3 -alkoxycarbonyl-Ci-C3 -alkyl, cyano-Ci-C 3 -alkyl, 10 benzyl, which may be substituted by halogen, Ci-C 4 -alkyl or trifluoromethyl, or is phenyl, which may be substituted by halogen, Ci-C 4 -alkyl, trifluoromethyl or Ci-C 4 -alkoxy; 15
R
3 is hydrogen, fluorine or chlorine;
R
4 is chlorine, trifluoromethyl or cyano; 20 R 5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -haloalkoxy, Ci-C 6 -haloalkylthio, Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)carbonyl, Ci-C 6 -alkylthio-(Ci-C6 -alkyl)carbonyl, (Ci-C 6 -alkyl)iminooxycarbonyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, 25 C 1
-C
6 -alkoxyamino-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkylamino-Ci-C 6 -alkyl, is Ci-C 6 -alkoxy, CI-C 6 -alkylthio, C 3
-C
6 -cycloalkoxy,
C
3
-C
6 -cycloalkylthio, C 2
-C
6 -alkenyloxy, C 2
-C
6 -alkenylthio, 30 C 2
-C
6 -alkynyloxy, C 2
-C
6 -alkynylthio, (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -alkyl)carbonylthio, (Ci-C 6 -alkoxy)carbonyloxy,
(C
2
-C
6 -alkenyl)carbonyloxy,
(C
2
-C
6 -alkenyl)carbonylthio,
(C
2
-C
6 -alkynyl)carbonyloxy,
(C
2
-C
6 -alkynyl)carbonylthio, Ci-C 6 -alkylsulfonyloxy or 35 Ci-C 6 -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, C 3
-C
6 -cycloalkyl, 40 CI-C 6 -alkoxy, C 3
-C
6 -cycloalkoxy, C 3
-C
6 -alkenyloxy,
C
3
-C
6 -alkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C 6 -alkylideneaminooxy, oxo,
=N-OR
1 3 45 52 - 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, 5 C 1
-C
6 -alkyl, C 1
-C
6 -haloalkyl, C 1
-C
6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; - -CO-R 1 4 , -CO-OR 1 4 , -CO-SR 1 4 , -CO-N(R 1 4
)-R
1 5 , -OCO-R 1 4 ,
-OCO-OR
1 4 ', -OCO-SR 1 4 ', -OCO-N(R1 4
)-R
1 5 , -N(R 1 4
)-R
1 5 , 10 and -C(R1 6
)=N-OR
1 3 ; is C(Z')-R 1 7 , -C(=NR 18
)R
1 7 , C(R 1 7
)(Z
2
R
1 9
)(Z
3
R
20 ),
C(R
1 7
)=C(R
2 1 )-CN, C(R1 7
)=C(R
21
)-CO-R
22 ,
-CH(R
17
)-CH(R
2 1
)-COR
22 , -C(R 17
)=C(R
2 1
)-CH
2
-CO-R
22 , 15 -C(R 1 7
)=C(R
2 1
)-C(R
2 3
)=C(R
2 4
)-CO-R
2 2 ,
-C(R
1 7
)=C(R
2 1
)-CH
2
-CH(R
2 5
)-CO-R
2 2 , -CO-OR 2 6 , -CO-SR 2 6 ,
-CON(R
2 6
)-OR
1 3 , -C=C-CO-NHOR 13 , -C=C-CO-N(R 2 6
)-OR
1 3 ,
-C=C-CS-NH-OR
1 3 , -C=C-CS-N(R 2 6 )-OR1 3 , -C(R1 7
)=C(R
2 1
)-CO-NHOR
1 3 , -C(R 1 7
)=C(R
2 1
)-CO-N(R
2 6
)-OR
1 3, 20 -C(R 1 7
)=C(R
2 1 )-CS-NHOR1 3 , -C(R 1 7
)=C(R
2 1
)-CS-N(R
2 6
)-OR
1 3 ,
-C(R
17
)=C(R
2 1
)-C(R
16
)=N-OR
1 3 , C(R 1 6
)=N-OR
1 3 ,
-C=C-C(R
1 6
)=NOR
1 3 , C(Z 2
R
1 9
)(Z
3
R
2 0
)-OR
2 6 ,
-C(Z
2
R
1 9
)(Z
2
R
2 0
)SR
2 6 , C(Z 2
R
1 9
)(Z
3
R
2 0
)-N(R
2 7
)R
2 8 , -N(R 2 7
)-R
2 8 , -CO-N(R27)-R28 or -C(R 17
)=C(R
2 1
)CO-N(R
27
)R
28 ; in which Z 1 , 25 Z 2 , Z 3 independently of one another are oxygen or sulfur;
R
6 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, C 3
-C
7 -cycloalkyl, or is 3- to 7-membered saturated heterocyclyl which contains one or more oxygen 30 and/or sulfur atoms;
R
7 is hydrogen or Ci-C 6 -alkyl;
R
8 is hydrogen or Ci-C 3 -alkyl; 35
R
9 is hydrogen, Ci-C 3 -alkyl
R
8 and R 9 together are C=0; 40 R 10 is Ci-Ci 5 -alkyl, C 3 -C8-cycloalkyl, C 2 -Cio-alkenyl,
C
3 -Cio-alkynyl, Ci-C 6 -haloalkyl, C 1
-C
6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C3-C 6 -alkenyloxy-C 1
-C
6 -alkyl, C3-C 6 -alkynyloxy-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, 45 53 is phenyl or benzyl which may in each case be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, amino, C2-C 4 -monoalkylamino, Ci-C 4 -dialkylamino, 5 Ci-C 4 -alkoxycarbonyl, nitro or cyano;
R
11 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy;
R
12 is hydrogen, Ci-C 6 -alkyl, C 2
-C
6 -alkenyl, C 2
-C
6 -alkynyl, 10 Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, phenyl or benzyl which may be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -dialkylamino, Ci-C 4 -alkoxycarbonyl, nitro or cyano; or 15
R
11 and R 12 together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle;
R
12 ' is as defined for R 12 , but excluding hydrogen; 20
R
13 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl, C 3
-C
6 -alkynyl, Ci-C 6 -alkoxy-Cl-C 6 -alkyl, cyano-Ci-C 6 -alkyl, (Ci-C6-alkoxy)carbonyl-Ci-C 6 -alkyl or phenylalkyl, where 25 the phenyl ring may be mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, CI-C 3 -haloalkyl or Ci-C 3 -alkoxy;
R
14 is hydrogen, Ci-C 6 -alkyl, C 3
-C
6 -cycloalkyl, C 3
-C
6 -alkenyl, 30 C 3
-C
6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C6-alkoxy)carbonyl-Ci-C 6 -alkyl, C3-C6-alkenyloxycarbonyl-Cl-C6-alkyl, is phenyl or benzyl which may be unsubstituted on the 35 phenyl ring or may be mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, CI-C 3 -haloalkyl or Ci-C 3 -alkoxy;
R
14 ' is as defined for R 14 , but excluding hydrogen; 40
R
15 is hydrogen, hydroxyl, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, (Ci-C3-alkoxy)carbonyl-Ci-C3-alkoxy, C 3
-C
6 -alkenyl or
C
3
-C
6 -alkynyl; 45 R 16 is hydrogen, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, C3-C 6 -alkenyloxy, (Ci-C6-alkoxy)carbonylalkoxy, C 2
-C
6 -alkenyl, 54
(C
2
-C
6 -alkenyl)carbonyloxy, C 3
-C
6 -alkynyl,
(C
2
-C
6 -alkynyl)carbonyloxy, is phenyl, phenoxy or benzyl, where the phenyl rings of 5 the 3 last-mentioned radicals may be unsubstituted or mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl, Ci-C 3 -alkoxy or (Ci-C 3 -alkoxy)carbonyl; 10 R 17 is hydrogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
C
2
-C
6 -alkenyl, C 2
-C
6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl;
R
18 is hydrogen, Ci-C 6 -alkyl, C 3
-C
6 -alkenyl, C 3
-C
6 -alkynyl, 15 C 3
-C
6 -cycloalkyl, Ci-C 6 -haloalkyl,
CI-C
6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, is phenyl or phenyl-(Ci-C 6 -alkyl), where the two 20 last-mentioned phenyl radicals may be substituted by halogen, cyano, nitro, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl, Ci-C 3 -alkoxy or (Ci-C 3 -alkoxy)carbonyl;
R
19 , R 2 0 independently of one another are Ci-C 6 -alkyl, 25 Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl, C 3
-C
6 -alkynyl,
C
1
-C
6 -alkoxy-CI-C 6 -alkyl, or
R
1 9 and R 2 0 together are a saturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a carbon 30 atom of this chain which is not adjacent to the variables
Z
2 and Z 3 may be replaced by -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)- and where the carbon chain may be substituted once to three times by halogen or Ci-C 6 -alkyl; 35
R
21 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl or Ci-C 6 -alkoxy;
R
22 is hydrogen, OR 3 1 , S-R 3 1 , CI-C 6 -alkyl, which may carry one 40 or two Ci-C 6 -alkoxy substituents, is C 2
-C
6 -alkenyl,
C
2
-C
6 -alkynyl, Ci-C 6 -haloalkyl or C 3
-C
6 -cycloalkyl;
R
23 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, C 3
-C
6 -alkenyl or
C
3
-C
6 -alkynyl; 45 55
R
24 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy or Ci-C 6 -haloalkyl;
R
25 is hydrogen, cyano or Ci-C 6 -alkyl; 5
R
26 , R 31 independently of one another are hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2
-C
6 -alkenyl or
C
2
-C
6 -alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: 10 cyano, halogen, Ci-C 6 -alkoxy, Ci-C 6 -alkylcarbonyl, (Ci-C 6 -alkoxy)carbonyl; or are (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, phenyl or phenyl-Ci-C 6 -alkyl; 15 R 27 , R 28 , R 29 , R 3 0 independently of one another are hydrogen, Ci-C 6 -alkyl, C 3
-C
6 -alkenyl, C 2
-C
6 -alkynyl,
C
3
-C
6 -cycloalkyl, Ci-C 6 -haloalkyl,
C
1
-C
6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, (Ci-C 6 -alkoxy)carbonyl, or 20
R
2 7 and R 28 and/or R 2 9 and R 30 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 25 an -NH- group; m is 0, 1, 2 or 3.
R
4 is in particular halogen and specifically fluorine or chlorine. 30 RA is in particular hydrogen, i.e. m is 0. In Ql, R 5 is, in particular: Ci-C 6 -alkoxy, C 2
-C
6 -alkenyloxy or C 2
-C
6 -alkynyloxy, where 35 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-C 6 -alkoxy,
C
3
-C
6 -alkenyloxy, C 3
-C
6 -alkynyloxy, Ci-C 6 -alkylsulfonyl,
-CO-R
1 4 , -CO-OR 1 4 , -CO-N(R1 4 )-Ri 5 , -N(R 1 4 )-Ri 5 and 40 -C(R 1 6
)=N-OR
1 3 ;
-CO-R
1 7 , -C(NR 1 8
)-R
1 7 , -C(R 1 7
)(OR
1 9
)(OR
2 0 ),
-C(R
1 7
)=C(R
2 1)-CO-R 2 2 , -CH(R 1 7
)-CH(R
2 1)-CO-R 2 2 , -CO-OR 2 6 ,
-CO-N(R
2 6
)-OR
1 3 , -C(R 1 7
)=C(R
2 1
)-CO-N(R
2 6
)-OR
1 3 , 45 -C(R 1 6
)=N-OR
1 3 , -C(OR 1 9
)(OR
2 0
)-OR
2 6 , -N(R 2 7
)R
2 8 , -CON(R 2 7
)R
2 8 or -C(R17)=C(R27)CO-N(R27)R28 56 in which R 13 to R 22 and R 26 to R 28 are as defined above, and specifically C 2
-C
6 -alkenyloxy, C 2
-C
6 -alkynyloxy,
-C(R
17
)(OR
19
)(OR
2 0 ), -C(R 1 7
)=C(R
21
)-C(O)R
21 , 5 -CH(R 17
)-CH(R
2 1
)-C(O)R
2 2 , C(O)OR 2 6 , -C(O)-N(R 26
)-OR
13 , -C(Ri 6
)=N-OR
1 3 and C(O)N(R 2 7
)R
28 , in which R 13 , R 16 , R 17 , R 19 ,
R
2 0 , R 2 1 , R 22 , R 26 , R 2 7 and R 28 have the meanings mentioned above and in particular those mentioned below: 10 R 13 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -haloalkenyl, C 3
-C
6 -alkynyl, Ci-C 6 -cyanoalkyl or Ci-C 6 -alkoxycarbonyl-Cl-C 6 -alkyl;
R
16 is hydrogen, Ci-C 6 -alkyl, CI-C 6 -alkoxy, 15 Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkoxy or phenoxycarbonyl-Ci-C 6 -alkoxy;
R
17 is hydrogen, Ci-C 6 -alkyl; 20
R
19 and R 20 independently of one another are Ci-C 6 -alkyl;
R
21 is hydrogen, halogen, Ci-C 6 -alkyl; 25 R 22 is hydroxyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkoxycarbonyl-Ci-C6 -alkyl;
R
26 is Ci-C 6 -alkyl, C 3
-C
6 -haloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, 30 C 3
-C
6 -alkenyloxycarbonyl-Ci-C 6 -alkyl,
C
3
-C
6 -alkynyloxycarbonyl-Ci-C 6 -alkyl, CI-C 6 -alkoxyalkyl;
R
27 is hydrogen, Ci-C 6 -alkyl; 35 R 28 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, or R 2 7 and R 28 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring. 40 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: 45 57 Ci-C 6 -alkoxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NRilR 1 2 , -C(O)NHC(O)Cl, -C(O)NHS(0) 2 Cl, C(O)NHC(O)OR 1 2 ', C(O)NHS(0) 2
R
2 ', C(O)R 2 , P(O)R 1
(OR
1 ), P(O)(ORI) 2 ; S(O)R 2 , 5 S(O) 2
R
2 or S(O) 2
NHR
2 in which the variables R 1 , R 2 , R 11 , R 1 2 and R 1 2 ' have the meanings mentioned above and specifically those listed below: 10
R
1 is Ci-C 6 -alkyl
R
2 is Ci-C 6 -alkyl 15 R 11 is hydrogen or Ci-C 6 -alkyl
R
1 2 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, and
R
12 ' is Ci-C 6 -alkyl and Ci-C 6 -alkyloxy. 20 R is particularly preferably: hydrogen or is Ci-C 6 -alkoxycarbonyl or (Ci-C 4 -alkoxycarbonyl)iminocarbonyl. 25 A specific class relates to compounds of the formulae Ia and Ib in which Q is Ql. Here, the variables have the meanings mentioned above and particularly preferably those below: 30 R is Ci-C 6 -alkoxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NRilR1 2 , -C(O)NHC(0)Cl, -C(0)NHS(0)2Cl, C(0)NHC(0)OR12',
C(O)NHS(O)
2
R
1 2 ', C(O)R 2 , P(O)R 1
(OR
1 ), P(O)(OR 1
)
2 ; S(O)R 2 ,
S(O)
2
R
2 or S(O) 2
NHR
2 35 in which the variables R 1 , R 2 , R 11 , R 1 2 and R 1 2 ' have the following meanings:
R
1 is Ci-C 6 -alkyl, 40
R
2 is Ci-C 6 -alkyl,
R
11 is hydrogen or Ci-C 6 -alkyl, 45 R 1 2 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, and 58
R
1 2 ' is Ci-C 6 -alkyl or Ci-C 6 -alkyloxy; Z is o or S, in particular 0 5 X is O or S, m has the value 0,
R
3 is hydrogen or halogen, in particular fluorine or 10 chlorine,
R
4 is hydrogen, halogen, in particular fluorine or chlorine, or cyano, and 15 R 5 is Ci-C 6 -alkyl, C 3
-C
6 -alkenyl, Ci-C 6 -haloalkyl,
C
3
-C
6 -haloalkenyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 -haloalkylthio, C 3
-C
6 -alkenyloxy,
C
3
-C
6 -alkynyloxy, Ci-C 6 -haloalkenyloxy, C 3
-C
6 -alkenylthio,
C
3
-C
6 -haloalkenylthio, C 1
-C
6 -alkoxycarbonyl-Ci-C 6 -alkoxy, 20 C 3
-C
6 -alkenyloxycarbonyl-Ci-C 6 -alkoxy,
C
3
-C
6 -alkynyloxycarbonyl-Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkoxy,
C
3
-C
6 -alkenyloxycarbonyl-Ci-C 6 -alkoxycarbonyl Ci-C 4 -alkoxy, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkylthio, 25 Ci-C 6 -alkenyloxycarbonyl-Ci-C 6 -alkylthio, Ci-C 6 -alkynyloxycarbonyl-Ci-C6 -alkylthio, Ci-C 6 -alkoxy-Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkylthio, Ci-C 6 -alkoxyimino-Ci-C6 -alkyl, N-Ci-C 6 -alkoxy-N-(Ci-C 6 -alkyl)amino-Ci-C 6 -alkyl, 30 Ci-C 6 -alkylsulfonylamino, -COOR 2 6 , -CONR 2 7
R
2 8 ,
-C(=NR
1 8
)R
1 7 , -C(R 1 6 )=NOR1 3 , C(R 1 7
)=C(R
2 1
)-CO-R
2 2 , where the variables R 1 3 , R 1 6 , R 1 7 , R 2 1 , R 2 2 , R 2 6 to R 2 8 have the following meanings: 35
R
13 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -haloalkenyl, C 3
-C
6 -alkynyl, Ci-C 6 -cyanoalkyl or Ci-C 6 -alkoxycarbonyl-Ci-C6 -alkyl; 40 R 16 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkoxy or phenoxycarbonyl-Ci-C 6 -alkoxy; 45 R 1 7 is hydrogen, CI-C 6 -alkyl; 59
R
18 is Ci-C 6 -alkoxy;
R
2 1 is hydrogen, halogen, Ci-C 6 -alkyl; 5 R 22 is hydroxyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkoxycarbonyl-C 1
-C
6 -alkyl;
R
26 is Ci-C 6 -alkyl, C 3
-C
6 -haloalkyl, C 3
-C
6 -alkenyl,
C
3
-C
6 -alkynyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, 10 C3-C6-alkenyloxycarbonyl-Cl-C 6 -alkyl, C3-C6-alkynyloxycarbonyl-Cl-C 6 -alkyl, Cl-C 6 -alkoxyalkyl;
R
27 is hydrogen, Ci-C 6 -alkyl; 15 R 28 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, or R 2 7 and R 2 8 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring. 20 In particular, R 5 has the following meaning:
R
5 is CN, COOH, Ci-C4-alkoxyiminomethyl, Ci-C 4 -alkoxy,
C
3
-C
6 -cycloalkyloxy, C 3
-C
6 -alkenyloxy, C 3
-C
6 -alkynyloxy, 25 C3-C6-alkenyloxyiminomethyl,
(C
1
-C
4 -alkoxycarbonyl)-C2-C 6 -alkenyloxy,
C
3
-C
6 -alkynyloxyiminomethyl, 2-[Ci-C 4 -alkoxycarbonyl]-2-chloroethyl, 2-[Ci-C 4 -alkoxycarbonyl]-2-chloroethenyl, 30 Ci-C 4 -alkoxycarbonyl, (Ci-C6-alkoxycarbonyl)-Ci-C4-alkoxy, (Ci-C 6 -alkoxycarbonyl)-Ci-C 4 -thioalkyl, is COOR 2 6 , where R 2 6 = Ci-C 4 -alkoxy-Ci-C 4 -alkyl or C3-C6-alkenyloxycarbonyl-Ci-C 4 -alkyl, 35 is CONR 2 7
R
2 8 , where R 2 7 = hydrogen or Ci-C 4 -alkyl and R 2 8 = hydrogen, Ci-C 4 -alkyl or Ci-C 4 -alkoxy; is C(=NR1 7
)R
1 8 , in which R 1 7 is Ci-C 4 -alkoxy and R 18 is 40 Ci-C 4 -alkoxy or Ci-C4-alkoxycarbonyl-Ci-C 4 -alkoxy. Two further classes relate to compounds of the formulae Ia and Ib in which Q is Q2 or Q3. Here, the variables, independently of one another, particularly preferably have the following meanings: 45 60 R is Ci-C 6 -alkoxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NRilRl 2 , -C(O)NHC(O)Cl, -C(O)NHS(0) 2 Cl, C(O)NHC(0)OR 2 ',
C(O)NHS(O)
2
R
1 2 ', C(O)R 2 , P(O)Rl(ORI), P(O)(OR 1
)
2 ; S(O)R 2 , 5 S(O) 2
R
2 or S(O) 2
NHR
2 in which the variables R 1 , R 2 , R 11 , R 1 2 and R 1 2 ' have the following meanings: 10 R 1 is Ci-C 6 -alkyl,
R
2 is Ci-C 6 -alkyl, Ril is hydrogen or Ci-C 6 -alkyl, 15
R
12 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, and
R
12 ' is CI-C 6 -alkyl or CI-C 6 -alkyloxy; 20 Z is 0 or S, in particular 0, X is O or S, m has the value 0, 25
R
3 is hydrogen or halogen,
R
4 is hydrogen or halogen, 30 Y is O or S, U is a single bond, oxygen or Ci-C 4 -alkylene and
R
6 is hydrogen, halogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, 35 C 3
-C
7 -cycloalkyl, saturated C 3
-C
7 -heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, is Ci-C 6 -alkoxyalkyl, cyano-Ci-C 6 -alkyl, CO 2 H, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C 3
-C
6 -alkenyl or 40 C 3
-C
6 -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: 45 61 R is Ci-C 6 -alkoxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NRllRl 2 , -C(O)NHC(O)Cl, -C(O)NHS(0) 2 Cl, C(O)NHC(O)OR 1 2 ',
C(O)NHS(O)
2
R
1 2 ', C(O)R 2 , P(O)R 1
(OR
1 ), P(O)(OR 1
)
2 ; S(O)R 2 , 5 S(O) 2
R
2 or S(O) 2
NHR
2 in which the variables RI, R 2 , R 11 , R 1 2 and R 1 2 ' have the following meanings: 10 R 1 is Ci-C 6 -alkyl,
R
2 is Ci-C 6 -alkyl,
R
11 is hydrogen or Ci-C 6 -alkyl, 15
R
12 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, and
R
12 ' is Ci-C 6 -alkyl and Ci-C 6 -alkyloxy; 20 Z is 0 or S, in particular 0, X is O or S, m has the value 0, 25
R
3 is hydrogen or halogen, Y is O or S, 30 Y' in the formula Q5 is oxygen or sulfur, T is a single bond, oxygen or Ci-C 4 -alkylene and
R
7 is hydrogen, halogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, 35 C 3
-C
7 -cycloalkyl, saturated C 3
-C
7 -heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, Ci-C 6 -alkoxyalkyl, cyano-Ci-C 6 -alkyl, CO 2 H, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C 3
-C
6 -alkenyl or 40 C 3
-C
6 -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: 45 62 R is Ci-C 6 -alkoxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NRilR 1 2 , -C(O)NHC(O)Cl, -C(O)NHS(0) 2 Cl, C(O)NHC(O)OR 1 2 ',
C(O)NHS(O)
2
R
1 2 ', C(O)R 2 , P(O)R1(ORI), P(O)(OR 1
)
2 ; S(O)R 2 , 5 S(O) 2
R
2 or S(O) 2
NHR
2 in which the variablea R 1 , R 2 , R 11 , R 1 2 and R 1 2 ' have the following meanings: 10 R 1 is Ci-C 6 -alkyl,
R
2 is Ci-C 6 -alkyl,
R
11 is hydrogen or Ci-C 6 -alkyl, 15
R
12 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy, and
R
12 ' is Ci-C 6 -alkyl or Ci-C 6 -alkyloxy; 20 Z is 0 or S, in particular 0, X is O or S, m has the value 0, 25
R
3 is hydrogen or halogen,
R
4 is hydrogen or halogen, where 30 R 8 and R 9 independently of one another are hydrogen, Ci-C 6 -alkyl, halogen, cycloalkyl or Ci-C 6 -haloalkyl, or
R
8 and R 9 together with the carbon atom to which they are attached are a carbonyl group. 35 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 40 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, 45 in which 63 Q is Q1, Z is oxygen, 5 X is oxygen or sulfur, m has the value 0, R is hydrogen, Ci-C4-alkoxycarbonyl or 10 (Ci-C 4 -alkoxycarbonyl)iminocarbonyl,
R
3 is fluorine, chlorine or hydrogen,
R
4 is halogen, and 15
R
5 is CN, COOH, Ci-C4-alkoxyiminomethyl, CI-C 4 -alkoxy, C3-C 6 -cycloalkyloxy, C 3
-C
6 -alkenyloxy, C3-C 6 -alkynyloxy, C3-C 6 -alkenyloxyiminomethyl, (Ci-C 4 -alkoxycarbonyl)-C2-C 6 -alkenyloxy, 20 C3-C 6 -alkynyloxyiminomethyl, 2-[Ci-C4-alkoxycarbonyl]-2-chloroethyl, 2-[Ci-C 4 -alkoxycarbonyl]-2-chloroethenyl, Ci-C 4 -alkoxycarbonyl, (Ci-C 6 -alkoxycarbonyl)-Ci-C 4 -alkoxy, (Ci-C 6 -alkoxycarbonyl)-Ci-C 4 -thioalkyl, 25 is COOR 26 , where R 26 = Ci-C 4 -alkoxy-Ci-C 4 -alkyl or C3-C6-alkenyloxycarbonyl-Cl-C4-alkyl, is CONR 2 7
R
28 , where R 2 7 = hydrogen or Ci-C 4 -alkyl and R 28 = 30 is hydrogen, Ci-C 4 -alkyl or Ci-C 4 -alkoxy; is C(=NR1 7 )Rl8, in which R 1 7 is Ci-C 4 -alkoxy and R 18 is Ci-C 4 -alkoxy or Ci-C4-alkoxycarbonyl-Cl-C 4 -alkoxy. 35 40 45 64 Particularly preferred compounds of the formula Ia are the compounds Ial.1 to Ial.206 listed in Table 1 below. 5 Table 1
R
3 x N INH R4 la 10 I 10 Zl-,NO2s 15 No. Z X R 3 R4 R5 I a.1 0 S H Cl OCH 2 C=CH I a.2 0 S H Cl OCH 2
CH=CH
2 20 I a.3 0 S H Cl OCH(CH 3 )C=CH I a.4 0 S F Cl OCH 2 C=CH I a.5 0 S F Cl OCH 2
CH=CH
2 I a.6 0 S F Cl OCH(CH 3 )C=CH 25 I a.7 0 S H Cl CO 2
CH
3 I a.8 0 S H Cl CO 2
CH
2
CH=CH
2 I a.9 0 S H Cl CO 2
CH
2 C.CH I a.10 0 S H Cl CO 2
CH
2
CH
2 0CH 3 30 1a.11 0 S F Cl CO 2
CH
3 I a.12 0 S F C1 CO 2
CH
2
CH=CH
2 I a.13 0 S F Cl CO 2
CH
2 C=-CH I a.14 0 S F Cl CO 2
CH
2
CH
2 0CH 3 I a.15 0 S H CN OCH 2 C=CH 35 I a.16 0 S F CN OCH 2 CmCH I a.17 0 S H Cl OCH 2
CO
2
CH
3 I a.18 0 S H Cl OCH 2
CO
2
CH
2 C=CH I a.19 0 S H Cl OCH 2
CO
2
CH
2
CH
2 0CH 3 40 I a.20 0 S H Cl OCH 2
CO
2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 I a.21 0 S F Cl OCH 2
CO
2
CH
3 I a.22 0 S F Cl OCH 2
CO
2
CH
2 C=CH I a.23 0 S F Cl OCH 2
CO
2
CH
2
CH
2 0CH 3 45 I a.24 0 S F Cl OCH(CH 3
)CO
2
CH
3 I a.25 0 S F Cl OCH(CH 3
)CO
2
C
2
H
5 i a.26 0 S F Cl OCHkCH 3 )C0 2 Ci 2
CH=CH
2 65 No. Z X R 3 R4 R5 I a.27 0 S F Cl OCH(CH 3
)CO
2
CH
2 C=CH I a.28 0 S F Cl OCH(CH 3
)CO
2
CH
2
CH
2 0CH 3 5 I a.29 0 S F Cl OCH 2
CO
2 -nC 5 Hii I a.30 0 S F Cl OCH(CH 3
)CO
2 -nC 5 Hii I a.31 0 S H Cl CO 2
CH
2
CO
2
CH
3 I a.32 0 S H Cl CO 2
CH
2
CO
2
C
2
H
5 I a.33 0 S H Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 10 I a.34 0 S F Cl C0 2
CH
2
CO
2
CH
3 I a.35 0 S F Cl C0 2
CH
2
CO
2
C
2
H
5 I a.36 0 S F Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 I a.37 0 S F CN C0 2
CH
3 15 I a.38 0 S F CN C0 2
C
2
H
5 I a.39 0 S F CN CO 2
CH
2
CH
2 0CH 3 I a.40 0 S F CN CO 2
CH
2
CO
2
CH
3 I a.41 0 S F CN CO 2
CH
2
CO
2
C
2
H
5 20 I a.42 0 S F CN CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 I a.43 0 S F CN OCH 2
CO
2
CH
3 I a.44 0 S F CN OCH 2
CO
2
C
2
H
5 I a.45 0 S F CN OCH 2
CO
2
CH
2 C=CH 25 I a.46 0 S F CN OCH 2
CO
2
CH
2
CH
2 0CH 3 I a.47 0 S F CN OCH(CH 3
)CO
2
CH
3 I a.48 0 S F CN OCH(CH 3
)CO
2
C
2
H
5 I a.49 0 0 F CN OCH(CH 3
)CO
2
CH
2
CH
2
OCH
3 I a.50 0 S H Cl NHSO 2
CH
3 30 I a.51 0 S H Cl NHSO 2
C
2
H
5 I a.52 0 S H Cl NHSO 2 -nC 3
H
7 I a.53 0 S H Cl NHSO 2 -iC 3
H
7 I a.54 0 S F Cl NHSO 2
CH
3 35 I a.55 0 S F Cl NHSO 2
C
2
H
5 I a.56 0 S F Cl NHSO 2 -nC 3
H
7 I a.57 0 S F Cl NHSO 2 -iC 3
H
7 I a.58 0 S F CN NHSO 2
CH
3 40 I a.59 0 S F CN NHS0 2
C
2
H
5 I a.60 0 S F CN NHSO 2 -nC 3
H
7 I a.61 0 S F CN NHSO 2 -iC 3
H
7 I a.62 0 S H Cl OCH 2 C(Cl)=CH 2 I a.63 0 S Cl Cl OCH 2 C(Cl)=CH 2 45 I a.64 0 S F Cl OCH 2 C(Cl)=CH 2 I a.6 5 0 S F CN OCH 2 C(Cl)=CH 2 66 No. Z X R 3 R4 5 I a.66 0 S Cl Cl OCH 2 CaCH I a.67 0 S Cl Cl OCH 2
CH=CH
2 5I a.68 0 S Cl Cl OCH7CO7CH 3 A I a.69 0 S Cl Cl OCH 2
CO
2 nC 5 Hll I a.70 0 S Cl Cl OCH(CH 3
)CO
2
CH
3 I a.71 0 S Cl Cl OCH(CH 3
)CO
2
CH
2
CH=CH
2 10I a.72 0 S Cl Cl OCH(CH 3
)CO
2
CH
2
CH
2
OCH
3 I a.73 0 S Cl Cl CO 2
CH
3 I a.74 0 S ICl Cl C0 2
C
2
H
5 I a.75 0 S Cl Cl CO 2
CH
2
CO
2
CH
3 I a.76 0 0 Cl Cl ICO 2
C(CH
3
)
2 C0 2
CH
3 15 1 a.77 0 S H Cl SCH 2 CmCH I a.78 0 S H Cl SCH 2
CH=CH
2 I a.79 0 S IH Cl SCH 2 C0 2
CH
3 I a.80 0 S H Cl SCH 2
CO
2 -nC 5 Hll 20 1 a.81 0 5 H Cl SCH(CH 3
)CO
2
CH
3 I a.82 0 S H Cl ISCH(CH 3 )C0 2
CH
2
CH
2 0CH 3 I a.83 0 S IH Cl SCH 2
CO
2
CH
2
CH
2
OCH
3 I a.84 0 S H Cl OCF 2 CHFC1 25 1 a.85 0 5 Cl Cl SCH 2 C-CH I a.86 0 5 Cl Cl ISCH 2
CH=CH
2 I a.87 0 S Cl Cl SCH 2
CO
2
CH
3 I a.88 0 5 Cl Cl SCH 2
CO
2 -nC 5 Hll I a.89 0 5 Cl Cl SCH(CH 3
)CO
2
CH
3 30I a.90 0 5 Cl Cl SCH(CH 3
)CO
2
CH
2
CH
2
OCH
3 I a.91 0 S Cl Cl ISCH 2
CO
2
CH
2
CH
2
OCH
3 I a.92 0 5 Cl Cl OCF 2 CHFC1 I a.93 0 IS F Cl SCH 2 CmCH 35 1 a.94 0 S F Cl SCH 2
CH=CH
2 I a.95 0 S F Cl SCH 2
CO
2
CH
3 I a.96 0 5 F Cl ISCH 2
CO
2 -nC 5 Hll I a.97 0 5 F Cl SCH(CH 3
)CO
2
CH
3 40 1 a.98 0 S F Cl SCH(CH 3
)CO
2
CH
2
CH
2
OCH
3 I a.99 0 S F Cl SCH 2
CO
2
CH
2
CH
2
OCH
3 I a.100 0 S F Cl OCF 2 CHFC1 I a.101 0 S F CN SCH 2 CmCH 45I a.102 0 5 F CN SCH 2
CH=CH
2 I a.103 0 0 F CN~ SCH 2
CO
2
CH
3 Ta1410 S F CN 1CH 2 C0 2 -nC 5 Hl 11 67 No. Z X R 3 R4 5 I a. 105 0 S F CN SCH(CH 3
)CO
2
CH
3 I a. 106 0 S F CN SCH(CH 3
)CO
2
CH
2
CH
2
OCH
3 5I a. 107 0 S F CN SCH 2
CO
2
CH
2
CH
2
OCH
3 I a.108 0 S H cl C(0)N(CH 3
)
2 I a.109 0 S F Cl C(O)N(CH 3
)
2 I a.110 0 S F CN C(0)N(CH 3
)
2 10I a.111 0 S H Cl C(0)-N(C 2
H
4
)
2 0 I a.112 0 S H F C(O)-N(C 2
H
4
)
2 0 I a.113 0 S H Cl CH=N-OCH 3 I a.114 0 S H Cl ICH=N-0C 2
H
5 I a.115 0 S H Cl C(0)NHOCH 3 15 1 a.116 0 S H Cl C(O)NHOC 2
H
5 I a.117 0 S H Cl C(=N-OCH 3
)OCH
3 I a.118 0 S H Cl C(=N-OCH 3 )0C 2
H
5 I a.119 0 S H Cl C(=N-OCH 3
)OCH
2
CO
2
CH
3 20 1 a.120 0 S H Cl C(=N-OCH 3
)OCH(CH
3
)CO
2
CH
3 I a.121 0 S H Cl CH=CH-CO 2
CH
3 I a.122 0 S H Cl CH=CH-C0 2
C
2
H
5 I a.123 0 S H Cl CH=C(CH 3
)CO
2
CH
3 25 1 a.124 0 S H Cl CH=C(CH 3 )C0 2
C
2
H
5 I a.125 0 S H Cl CH=C(Cl)CO 2
CH
3 I a.126 0 S H Cl CH=C (C1) C0 2
C
2
H
5 I a.127 0 S H Cl CH=C(Br)CH 2
C
2
H
5 30I a.128 0 S H Cl CH 2
N(CH
3
)OCH
3 Ia19 0 0 H Cl C(=N-OCH 3
)OCH
2
CO
2 phenyl I a.130 0 IS H F CH=N-0C 2
H
5 I a.131 0 S H F C(O)NHOCH 3 I a.132 0 S H F C(O)NHOC 2
H
5 35 1 a.133 0 S H F C(=N-OCH 3
)OCH
3 I a.134 0 S H F C(=N-OCH 3 )0C 2
H
5 I a.135 0 S H F C(=N-OCH 3 )0CH 2
CO
2
CH
3 I a.136 0 IS IH F C(=N-OCH 3
)OCH(CH
3
)CO
2
CH
3 40 1 a.137 0 S H F CH=CH-CO 2
CH
3 I a.138 0 S H F CH=CH-C0 2
C
2
H
5 I a.139 0 S H F CH=C(CH 3
)CO
2
CH
3 I a.140 0 S H F CH=C(CH 3 )C0 2
C
2
H
5 45I a.141 0 S H F CH=C(Cl)CO 2
CH
3 I a.142 0 S H IF CH=C(Cl)C0 2
C
2
H
5 a.143. 0 S IF IF CR=C r) C0 2 2 'Hr- 68 No. Z X R 3 R4 5 I a. 144 0 S H F CH 2
N(CH
3
)OCH
3 I a.145 0 S H F C(=N-OCH 3
)OCH
2
CO
2 phenyl 5I a.146 0 IS H F ICH=N-OCH 3 I a.147 0 IS IF CN CH=N-OCH 3 I a..148 0 S F CN CH=N-0C 2
H
5 I a.149 0 S F- CN C(0)NH0CH 3 I a.150 0 S F CN C(0)NHOC 2
H
5 10 I a.151 0 S IF CN C(=N-0CH 3
)OCH
3 I a.152 0 S F CN C(=N-OCH 3 )0C 2
H
5 I a.153 0 S F CN C (=N-OCH 3 ) OCH 2 C0 2
CH
3 I a.154 0 S F CN C (=N-0CH 3 )0OCH (CH 3 ) C0 2
CH
3 15 1 a.155 0 0 F CN CH=CH-CO 2
CH
3 I a.156 0 S F CN CH=CH-C0 2
C
2
H
5 I a.157 0 S F CN ICH=C(CH 3
)CO
2
CH
3 I a.158 0 S F CU CH=C(CH 3 )C0 2
C
2
H
5 20 1 a.159 0 S F CN CH=C(Cl)CO 2
CH
3 I a.160 0 S F CU CH=C(Cl)C0 2
C
2
H
5 I a.161 0 S F CU CH=C(Br)C0 2
C
2
H
5 I a.162 0 S F CU CH 2
-N(CH
3
)OCH
3 25 1 a.163 0 S F CU C(N-0CH 3 )0CH 2 C0 2
C
6
H
5 I a.164 0 S H Cl CH=N-0CH 2 -CmCH I a.165 0 S H Cl CH=N-OCH 2 -C(C1)=CH 2 I a.166 0 5 F Cl CH 2 -CH(Cl)C0 2
C
2
H
5 I a.167 0 S H Cl CH=N-OCH 2
CO
2
CH
3 301a18 0 5 H Cl CH=N-OCH 2
CO
2
C
2
H
5 I a.169 0 S H Cl CH=N-OCH 2
CH
2 Cl I a.170 0 5 H Cl CH=N-OCH 2 CN I a.171 0 5 H Cl CH=N-OCH(CH 3
)CO
2
CH
3 35 1 a.172 0 S H Cl CH=C(C1)COSCH 3 I a.173 0 S H Cl CH=C(Br)COSCH 3 I a.174 0 S H Cl CH=C(Cl)C0 2
CH
2
CO
2
CH
3 I a.175 0 S IH Cl CH=C (C1) C0 2 CH (CH 3 ) CO 2
CH
3 40 1 a.176 0 5 H Cl C(CH 3
)=NOCH
3 I a.177 0 S H Cl C(CH 3
)=NOC
2
H
5 I a.178 0 S H Cl C (CH 3 ) =NOCH 2
CO
2
CH
3 I a.179 0 S F Cl CH=N-OCH 2 C.-CH 45I a.180 0 S F Cl CH=N-OCH 2 -C(Cl)=CH 2 I a.181 0 S F Cl CH=N-OCH 2
CO
2
CH
3 I a. Ii;2 10 +0 F-- Cl C -7H=N-OCH-COTC 2
H
5 69 No. Z X R 3 R4 R5 I a.183 0 S F Cl CH=N-OCH 2
CH
2 Cl I a.184 0 S F Cl CH=N-OCH 2 CN 5 I a.185 0 S F Cl CH=N-OCH(CH 3
)CO
2
CH
3 I a.186 0 S F Cl CH=C(Cl)COSCH 3 I a.187 0 S F Cl CH=C(Br)COSCH 3 I a.188 0 S F Cl CH=C(Cl)CO 2
CH
2
CO
2
CH
3 10 I a.189 0 S F Cl CH=C(Cl)CO 2
CH(CH
3
)CO
2
CH
3 I a.190 0 S F Cl C(CH3)=N-OCH3 I a.191 0 S F Cl C(CH 3 )=N-OC2H5 I a.192 0 S F Cl C(CH 3 ) =N-OCH2CO2CH3 I a.193 0 S Cl Cl CH
=
N-0-OCH 2 CCH 15 I a.194 0 S Cl Cl CH=N-OCH 2 -C(Cl)=CHR I a.195 0 S Cl Cl CH=N-OCH 2 CO2CH3 I a.196 0 S Cl Cl CH=N-OCH 2
CO
2 C2H5 I a.197 0 S Cl Cl CH=N-OCH 2
CH
2 Cl 20 I a.198 0 S Cl Cl CH=N-OCH 2 CN I a.199 0 S Cl Cl CH=N-OCH(CH3)CO2CH3 I a.200 0 S Cl Cl CH=C(Cl)COSCH 3 I a.201 0 S Cl Cl CH=C(Br)COSCH 3 25 I a.202 0 S Cl Cl CH=C(Cl)CO 2
CH
2
CO
2
CH
3 I a.203 0 S Cl Cl CH=C(Cl)CO 2
CH(CH
3
)CO
2
CH
3 I a.204 0 S Cl Cl C(CH 3
)=NOCH
3 I a.205 0 S Cl Cl C(CH 3
)=NOC
2
H
5 I a.206 0 0 Cl Cl C(CH 3
)=NOCH
2
CO
2
CH
3 30 Furthermore, particular preference is given to the substituted ureas of the formula Ib, in particular to the compounds Ibl.1 to Ibl.206 which differ from the corresponding compounds Ial.1 to 35 Ial.206 only in that the N-substituents are inverted:
H
3
CO
2 C 4 R R Z NC RN lb 40 11 x 45 Preference is furthermore given to the compounds Ia 2 .1 to Ia 2 .206 in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 70 X R 3 Il C / \ R 4 Ia 2 5CO 2
C
2
H
5 5 10 Preference is furthermore given to the compounds Ib 2 .1 to Ib 2 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206:
CO
2
C
2
H
5 15 N R 3 r l lb 2 Z N S\ / x R 5 20 Preference is furthermore given to the compounds Ia 3 .1 to Ia 3 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25 x 11 N R4 la 3 30 CO 2 Preference is furthermore given to the compounds Ib 3 .1 to Ib 3 .206, 35 in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 6- Z ' NC 2 R 3 40N I. Ib x R 4 R
R
5 45 71 Preference is furthermore given to the compounds Ia 4 .1 to Ia 4 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 5 x R 3 Il C R4 NN N Ia 4 ZI IN, CO 2 5 10 Preference is furthermore given to the compounds Ib 4 .1 to Ib 4 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings 15 mentioned in rows 1 to 206: ,n-C4H, NC2 R 3 Z N Ib4 C' -' 20 I1 X R 4 R 25 Preference is furthermore given to the compounds Ia 5 .1 to Ia 5 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 30 4 NR Ia 5 rN CO2 5 "t-C 4
H
9 35 Preference is furthermore given to the compounds Ib 5 .1 to Ib 5 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 40 45 72 .- t-C4H N - 2
R
3 Z. NC -'J lb 5 5 II X R 4 R . 10 Preference is furthermore given to the compounds Ia 6 .1 to Ia 6 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 Il 15 N C / \ 4 H1 _ Ia 6 ZN
C-SCH
3 5 0 20 Preference is furthermore given to the compounds Ib 5 .1 to Ib 5 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25 0 r N' LSCH3R3 C 30 X R4
R
5 Preference is furthermore given to the compounds Ia 7 .1 to Ia 7 .206, 35 in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 II 40 N / 7 \ 4 Z N I CHO 5 45 73 Preference is furthermore given to the compounds Ib 7 .1 to Ib 7 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 5 W CHO N' R 3 Zy N,' l b7 II | X 4I R 10 R 5 Preference is furthermore given to the compounds Ia 8 .1 to Ia 8 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings 15 mentioned in rows 1 to 206: x R 3 If N W R 1a 8 I N 20 Z - N' C 25 Preference is furthermore given to the compounds 1b 8 .1 to 1b 8 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 30 N oN R3 r II X NC C R4la
R
5 35 Preference is furthermore given to the compounds Ia 9 .1 to Ia 9 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 40 45 74 x R 3 5 Z N,C-NHCH 3
R
5 II 0 10 Preference is furthermore given to the compounds Ib 9 .1 to Ib 9 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 0 ONs\NHCH 3 15 NC R 3 rII Z N,'C lb9 R4
R
5 20 Preference is furthermore given to the compounds Ia 10 .1 to Ia 1 0 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25 x R 3 N R Ia 10
N,C-NHOCH
3 5 II 30 0 Preference is furthermore given to the compounds Ib 10 .1 to 35 Ib'O.206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 0 \\ NHOCH 3 N R3 r 1 40 Z N, lb10 R4
R
5 45 75 Preference is furthermore given to the compounds Iall.1 to Iall.206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 5 x R 3 11 |C W -, R4 Z~ N C-N-C-CI 10 H 11 10 0 0 Preference is furthermore given to the compounds Ibil.1 to Ibil.206, in which the variables Z, X, R 3 , R 4 and R 5 each have the 15 meanings mentioned in rows 1 to 206: 0 O H 11 N-C-Cl NRS lb11 20 C' RilIb| X R 4 R5 25 Preference is furthermore given to the compounds Ia 12 .1 to Ia 12 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: x R 3 30 II iN : Ia1 2 Z N x 5
C-NHSO
2 CI II 0 35 Preference is furthermore given to the compounds Ib 12 .1 to IbI 2 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 40 45 76 \ NHSO 2 CI
R
3 1b12 5 ZIN,C X 4 x ~ R4 R . 10 Preference is furthermore given to the compounds Ia 1 3 .1 to Ia 1 3 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 Il 15 C 4 z N
C-NHCO
2
CH
3 0 20 Preference is furthermore given to the compounds Ib 1 3 .1 to Ib 13 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25 0
NHCO
2
CH
3 Rb13 30 XI 4 R
R
5 Preference is furthermore given to the compounds Ial 4 .1 to 35 Ia 1 4 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 II 40 r IN Ia 14 Z N
C-NHSO
2
CH
3 II 0 45 77 Preference is furthermore given to the compounds Ib1 4 .1 to Ib 1 4 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 5O\ _NHS 2
CH
3 R 44 10 R
R
5 Preference is furthermore given to the compounds Ia 1 5 .1 to Ia 15 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the 15 meanings mentioned in rows 1 to 206: X R 3 Il C / R la 5 I i _ a 20Z N
C-CH
3 11 0 25 Preference is furthermore given to the compounds Ib1 5 .1 to Ib1 5 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 0 30 C 3CH 3 lbl Z N,CA II | x R 4 R 35 R5 Preference is furthermore given to the compounds Ia 1 6 .1 to Ia 1 6 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 40 45 78 x R 3 Il CI Ia 16 5 Z1. I
P(O)CH
3
(OCH
3 ) 10 Preference is furthermore given to the compounds Ib1 6 .1 to Ia 1 6 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206:
P(O)CH
3
(OCH
3 ) 15 3 r N V6 C' X R4 20 R 5 Preference is furthermore given to the compounds Ia 17 .1 to Ia 17 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25 X R 3 Il C /- R4 la 17 Z N 1 5 30
P(O)(OCH
3
)
2 Preference is furthermore given to the compounds Ibl 7 .1 to 35 Ib 17 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206:
P(O)(OCH
3
)
2 N R 3 40 ' Ib17 C A x R R5 45 79 Preference is furthermore given to the compounds Ia 1 8 .1 to Ia 1 8 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 5 X R 3 11 || C~ / \R la' 8 I - Ra1 z N
S(O)CH
3 10 Preference is furthermore given to the compounds Ibi 8 .1 to Ib1 8 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the 15 meanings mentioned in rows 1 to 206:
S(O)CH
3 r R Ibia 20 Z NC' x R 4 R5 25 Preference is furthermore given to the compounds Ia 1 9 .1 to Ia 1 9 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: X R 3 II 30 4 riN :t9 z N
SO
2
CH
3 35 Preference is furthermore given to the compounds Ib' 9 .1 to Ib1 9 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 40 45 80
SO
2
CH
3 N R 3 3b19 5 Z NC' X R 4
R
5 10 Preference is furthermore given to the compounds Ia 20 .1 to Ia 2 0 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: x R 3 15 R4 r lN Wa 2 z- R
SO
2
NHCH
3 20 Preference is furthermore given to the compounds Ib 20 .1 to Ib 2 0 .206, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206: 25
SO
2
NHCH
3 N R 11 | 30 X 4
R
5 R6. Preference is furthermore given to the compounds Ia 21 to 40.1 to 35 Ia 2 1 to 40.206, in which the variables X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206 and the radical R has the meaning mentioned in the formulae Iai to Ia 20 : X R 3 II 40 'NQOR4 la 2 no R 45 81 Preference is furthermore given to the compounds Ib 2 1 to 40.1 to Ib 2 1 to 40.206, in which the variables X, R 3 , R 4 and R 5 each have the meanings mentioned in rows 1 to 206 and the radical R has the meaning mentioned in the formulae Ibi to Ib 20 : 5 R II H RaIb21 to40 10 1 O R4 Moreover, particular preference is given to the substituted ureas 15 of the formula Ia.bl x N" H - Ia.b' 20 Z NH O N
UR
6 25 in particular to the compounds listed in Table 2: Table 2 No. X Z Y U R 6 30 Ia.bl 1 S S 0 - H Ia.bl 2 S S 0 - CH 3 Ia.bl 3 S S 0 - C 2
H
5 Ia.bl 4 S S 0 - n-C 3
H
7 35 Ia.bl 5 S S 0 - i-C 3
H
7 Ia.bl 6 S S 0 - cyclopropyl Ia.bl 7 S S 0 - n-C 4
H
9 Ia.bl 8 s S 0 - sec-C 4
H
9 40 Ia.bl 9 S S 0 - I-C 4
H
9 Ia.bl 10 S S 0 - t-C 4
H
9 Ia.bl 11 S S 0 CH 2 cyclopropyl Ia.bl 12 S S 0 - cyclopentyl Ia.bl 13 S S 0 - cyclohexyl 45 Ia.bl 14 S S 0 - oxiran-2-yl Ia.bl 15 S S 0 - oxetan-2-yl 82 No. X Z Y U R 6 Ia.bl 16 S S 0 - tetrahydrofuran-2-yl Ia.bl 17 S S 0 - tetrahydropyran-2-yl 5Ia.bl 18 S S 0 - loxepan-2-yl Ia.bl 19 S S 0 - thiiran-2-yl Ia.bl 20 S S 0 - thietan-2-yl Ia.bl 21 S S 0 - tetrahydrothiofuran-2-yl Ia.bl 22 S S 0 - tetrahydrothiopyran-2-yl 10Ia.bl 23 S S 0 - thiepan-2-yl Ia.bl 24 s S 0 - oxetan-3-yl Ia.bl 25 S S 0 - tetrahydrofuran-3-yl Ia.bl 26 S S 0 - tetrahydropyran-3-yl 15 Ia.bl 27 S S 0 - oxepan-3-yl Ia.bl 28 S S 0 - thiethan-3-yl Ia.bl 29 S S 0 - tetrahydrothiofuran-3-yl Ia.bl 30 S S 0 - tetrahydrothiopyran-3-yl 20 Ia.bl 31 S S 0 - thiepan-3-yl Ia.bl 32 S S 0 - tetrahydropyran-4-yl lab 1 33 S S 0 - oxepan-4-yl Ia.bl 34 S S 0 - tetrahydrothiopyran-4-yl 25 Ia.bl 35 s S 0 - oxepan-4-yl Ia.bl 36 S S 0 - tetrahydrothiopyran-4-yl Ia.bl 37 S S 0 0 CH 3 Ia.bl 38 S S 0 0 C 2
H
5 Ia.bl 39 S S 0 0 n-C 3
H
7 30 Ia.bl 40 S 5 0 0 i-C 3
H
7 Ia.bl 41 S S 0 0 cyclopropyl Ia.bl 42 S S 0 - C0 2 H Ia.bl 43 S S 0 - CO 2
CH
3 35 Ia.bl 44 S S 0 - C0 2
C
2
H
5 Ia.bl 45 S S 0 - CH 2
CO
2
CH
3 Ia.bl 46 S S 0 - CH (CH 3 ) CO 2
CH
3 Ia.b 1 - 47 S S 0 10 CH 2
CO
2
CH
3 40 Ia.bl 48 S S 0 0 CH(CH 3
)CO
2
CH
3 Ia.bl 49 S S 0 - cl Ia.bl 50 S S 0 - CN Ia.bl 51 S S 0 - CH 2 C=-CH 45Ia.bl 52 S S 0 0 CH 2 C=-CH Ia.bl 53 S S 0 - CH 2 0CH 3 Ipa.bl 54 S S 0 - CH 2 CT4- 83 No. X Z Y U R 6 Ia.bl 55 S S 0 0 CH 2
CH
2 0CH 3 Ia.bl 56 S S 0 CH 2 cyclopentyl 5 Ia.bl 57 S 0 0 - H Ia.bl 58 S 0 0 - CH 3 Ia.bl 59 S 0 0 - C 2
H
5 Ia.bl 60 S 0 0 - n-C 3
H
7 Ia.bl 61 S 0 0 - I-C 3
H
7 Ia.bl 62 S 0 0 - cyclopropyl Ia.bl 63 S 0 0 - n-C 4
H
9 Ia.bl 64 S 0 0 - sec-C 4
H
9 Ia.bl 65 S 0 0 - i-C 4 H9 15 Ia.bl 66 S 0 0 - t-C 4 H9 Ia.bl 67 S 0 0 CH 2 cyclopropyl Ia.bl 68 S 0 0 - cyclopentyl Ia.bl 69 S 0 0 - cyclohexyl 20 Ia.bl 70 S 0 0 - oxiran-2-yl Ia.bl 71 S 0 0 - oxetan-2-yl Ia.bl 72 S 0 0 - tetrahydrofuran-2-yl Ia.bl 73 S 0 0 - tetrahydropyran-2-yl 25 Ia.bl 74 S 0 0 - oxepan-2-yl Ia.bl 75 S 0 0 - thiiran-2-yl Ia.bi 76 S 0 0 - thietan-2-yl Ia.bl 77 S 0 0 - tetrahydrothiofuran-2-yl Ia.bl 78 S 0 0 - tetrahydrothiopyran-2-yl Ia.bl 79 S 0 0 - thiepan-2-yl Ia.bl 80 S 0 0 - oxetan-3-yl Ia.bl 81 S 0 0 - tetrahydrofuran-3-yl Ia.bl 82 S 0 0 - tetrahydropyran-3-yl 35 Ia.bl 83 S 0 0 - oxepan-3-yl Ia.b 1 84 S 0 0 - thiethan-3-yl Ia.bl 85 S 0 0 - tetrahydrothiofuran-3-yl Ia.b 1 86 S 0 0 - tetrahydrothiopyran-3-yl 40 Ia.bl 87 S 0 0 - thiepan-3-yl Ia.bl 88 S 0 0 - tetrahydropyran-4-yl Ia.bl 89 S 0 0 - oxepan-4-yl Ia.bl 90 S 0 0 - tetrahydrothiopyran-4-yl Ia.bl 91 S 0 0 - oxepan-4-yl 45 Ia.bl 92 S 0 0 - tetrahydrothiopyran-4-yl Iabl 93 5 0 0 0 CH 3 T-1 84 No. X Z Y U R 6 Ia.bl 94 S 0 0 0 C 2
H
5 Ia.bi 95 S 0 0 0 n-C 3
H
7 5 Ia.bl 96 S 0 0 0 i-C 3
H
7 Ia.bl 97 S 0 0 0 cyclopropyl Ia.bl 98 S 0 0 - CO 2 H Ia.bl 99 S 0 0 - CO 2
CH
3 Ia.bl 100 S 0 0 - CO 2
C
2
H
5 Ia.bl 101 S 0 0 - CH 2
CO
2
CH
3 Ia.bl 102 S 0 0 - CH(CH 3
)CO
2
CH
3 Ia.bl 103 S 0 0 0 CH 2
CO
2
CH
3 Ia.bl 104 S 0 0 0 CH(CH 3
)CO
2
CH
3 15 Ia.bl 105 S 0 0 - Cl Ia.bl 106 S 0 0 - CN Ia.bl 107 S 0 0 - CH 2 CwCH Ia.bl 108 S 0 0 0 CH 2 C=CH 20 Ia.bl 109 S 0 0 - CH 2 0CH 3 Ia.bl 110 S 0 0 - CH 2
CH
2 0CH 3 Ia.bl 111 S 0 0 0 CH 2
CH
2 0CH 3 Ia.bl 112 S 0 0 CH 2 cyclopentyl 25 Ia.bl 113 0 S 0 - H Ia.bl 114 0 S 0 - CH 3 Ia.bl 115 0 S 0 - C 2
H
5 Ia.bl 116 0 S 0 - n-C 3
H
7 Ia.bl 117 0 S 0 - I-C 3
H
7 30 Ia.bl 118 0 S 0 - cyclopropyl Ia.bl 119 0 S 0 - n-C 4
H
9 Ia.bl 120 0 S 0 - sec-C 4 H9 Ia.bl 121 0 S 0 - i-C 4
H
9 35 Ia.bl 122 0 S 0 - t-C 4 H9 Ia.bl 123 0 S 0 CH 2 cyclopropyl Ia.bl 124 0 S 0 - cyclopentyl Ia.bl 125 0 S 0 - cyclohexyl 40 Ia.bl 126 0 S 0 - oxiran-2-yl Ia.bl 127 0 S 0 - oxetan-2-yl Ia.bl 128 0 S 0 - tetrahydrofuran-2-yl Ia.bl 129 0 S 0 - tetrahydropyran-2-yl Ia.bl 130 0 S 0 - oxepan-2-yl 45 Ia.bl 131 0 S 0 - thiiran-2-yl Ia.bl 132 0 s O0 - thietan-2-yl 85 No. X Z Y U R 6 Ia.bl 133 0 S 0 - tetrahydrothiofuran-2-yl Ia.bl 134 0 S 0 - tetrahydrothiopyran-2-yl 5 Ia.bl 135 0 S 0 - thiepan-2-yl Ia.bl 136 0 S 0 - oxetan-3-yl Ia.bl 137 0 S 0 - tetrahydrofuran-3-yl Ia.bl 138 0 S 0 - tetrahydropyran-3-yl Ia.bl 139 0 S 0 - oxepan-3-yl Ia.bl 140 0 S 0 - thiethan-3-yl Ia.bl 141 0 S 0 - tetrahydrothiofuran-3-yl Ia.bl 142 0 S 0 - tetrahydrothiopyran-3-yl Ia.bl 143 0 S 0 - thiepan-3-yl 15 Ia.bl 144 0 S 0 - tetrahydropyran-4-yl Ia.bl 145 0 S 0 - oxepan-4-yl Ia.bl 146 0 S 0 - tetrahydrothiopyran-4-yl Ia.bl 147 0 S 0 - oxepan-4-yl 20 Ia.bl 148 0 S 0 - tetrahydrothiopyran-4-yl Ia.bl 149 0 S 0 0 CH 3 Ia.bl 150 0 S 0 0 C 2
H
5 Ia.bl 151 0 S 0 0 n-C 3
H
7 25 Ia.bl 152 0 S 0 0 i-C 3
H
7 Ia.bl 153 0 S 0 0 cyclopropyl Ia.bl 154 0 S 0 - CO 2 H Ia.bl 155 0 S 0 - CO 2
CH
3 Ia.bl 156 0 S 0 - C0 2
C
2
H
5 30 Ia.bl 157 0 S 0 - CH 2
CO
2
CH
3 Ia.bl 158 0 S 0 - CH(CH 3
)CO
2
CH
3 Ia.bl 159 0 S 0 0 CH 2
CO
2
CH
3 Ia.bl 160 0 S 0 0 CH(CH 3
)CO
2
CH
3 35 Ia.bl 161 0 S 0 - Cl Ia.bl 162 0 S 0 - CN Ia.bl 163 0 S 0 - CH 2 CmCH Ia.bl 164 0 S 0 0 CH 2 C=CH 40 Ia.bl 165 0 S 0 - CH 2 0CH 3 Ia.bl 166 0 S 0 - CH 2
CH
2 0CH 3 Ia.bl 167 0 S 0 0 CH 2
CH
2 0CH 3 Ia.bl 168 0 S 0 CH 2 cyclopentyl Ia.bl 169 0 0 [sic] 0 - H 45 Ia.bl 170 0 0 0 - CH 3 Ta.bl 171 0 - n-C3H7 86 No. X Z Y U R 6 Ia.bl 172 0 0 0 - i-C3H7 Ia.bl 173 0 0 0 - cyclopropyl 5 Ia.bl 174 0 0 0 - n-C 4
H
9 Ia.bl 175 0 0 0 - sec-C 4 H9 Ia.bl 176 0 0 0 - i-C 4 H9 Ia.bl 177 0 0 0 - t-C 4
H
9 Ia.bl 178 0 0 0 CH 2 cyclopropyl Ia.bl 179 0 0 0 - cyclopentyl Ia.bl 180 0 0 0 - cyclohexyl Ia.bl 181 0 0 0 - oxiran-2-yl Ia.bl 182 0 0 0 - oxetan-2-yl 15 Ia.bl 183 0 0 0 - tetrahydrofuran-2-yl Ia.bl 184 0 0 0 - tetrahydropyran-2-yl Ia.bl 185 0 0 0 - oxepan-2-yl Ia.bl 186 0 0 0 - thiiran-2-yl 20 Ia.bl 187 0 0 0 - thietan-2-yl Ia.bl 188 0 0 0 - tetrahydrothiofuran-2-yl Ia.bl 189 0 0 0 - tetrahydrothiopyran-2-yl Ia.bl 190 0 0 0 - thiepan-2-yl 25 Ia.bl 191 0 0 0 - oxetan-3-yl Ia.bl 192 0 0 0 - tetrahydrofuran-3-yl Ia.bl 193 0 0 0 - tetrahydropyran-3-yl Ia.bl 194 0 0 0 - oxepan-3-yl Ia.bl 195 0 0 0 - thiethan-3-yl 30 Ia.bl 196 0 0 0 - tetrahydrothiofuran-3-yl Ia.bl 197 0 0 0 - tetrahydrothiopyran-3-yl Ia.bl 198 0 0 0 - thiepan-3-yl Ia.bl 199 0 0 0 - tetrahydropyran-4-yl 35 Ia.bl 200 0 0 0 - oxepan-4-yl Ia.bl 201 0 0 0 - tetrahydrothiopyran-4-yl Ia.bl 202 0 0 0 - oxepan-4-yl Ia.bl 203 0 0 0 - tetrahydrothiopyran-4-yl 40 Ia.bl 204 0 0 0 0 CH 3 Ia.bl 205 0 0 0 0 C 2
H
5 Ia.bl 206 0 0 0 0 n-C 3
H
7 Ia.bl 207 0 0 0 0 i-C 3
H
7 Ia.bl 208 0 0 0 0 cyclopropyl 45 Ia.bl 209 0 0 0 - CO 2 H I. bl 210 0 0 0 - C0 2
CH
3 87 No. X Z Y U R 6 Ia.bl 211 0 0 0 - C0 2
C
2
H
5 Ia.bl 212 0 0 0 - CH 2
CO
2
CH
3 5 Ia.bl 213 0 0 0 - CH(CH 3
)CO
2
CH
3 Ia.bl 214 0 0 0 0 CH 2
CO
2
CH
3 Ia.bl 215 0 0 0 0 CH(CH 3
)CO
2
CH
3 Ia.bl 216 0 0 0 - Cl Ia.bl 217 0 0 0 - CN Ia.bl 218 0 0 0 - CH 2 C=CH Ia.bl 219 0 0 0 0 CH 2 C=CH Ia.bi 220 0 0 0 - CH 2 0CH 3 Ia.bl 221 0 0 0 - C 2
H
5 15 Ia.bl 222 0 0 0 - CH 2
CH
2 0CH 3 Ia.bl 223 0 0 0 0 CH 2
CH
2 0CH 3 Ia.bl 224 0 0 0 CH 2 cyclopentyl 20 Preference is furthermore given to the compounds Ib.bil to Ib.bl224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: N.H II 25 ZNI N,CN I bl 1b1b x 0 ,-N
UR
6 30 Preference is furthermore given to the compounds Ia.b 2 1 to Ia.b 2 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 35 x i C la.b2 ZN 0 , N 40
O
2
CH
3
UR
6 Preference is furthermore given to the compounds Ib.b 2 1 to Ib.b 2 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 88 CO 2 CH N 5 Ir I 5 C C1 Ib.b2 x O N UR' 10 Preference is furthermore given to the compounds Ia.b 3 1 to Ia.b 3 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: x 1 5 W CC 1a b r I Ia.b 3 Z N 'IO N 0 2
C
2
H
5 UR 6 20 Preference is furthermore given to the compounds Ib.b 3 1 to Ib.b 3 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 25 C0 2
CC
2
H
5 r N Z /N \ CI Ib.b3 x 30 O N UR' Preference is furthermore given to the compounds Ia.b 4 l to 35 Ia.b4224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: C1 x 40 I Ia.b 4 Z N O 7 N
UR
6 42CH5 UR 45 89 Preference is furthermore given to the compounds Ib.b 4 1 to Ib.b 4 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CO
2
CH
3 N Ci Z C /\Cl Ib.b4 OI N 10
UR
6 Preference is furthermore given to the compounds Ia.b 5 1 to Ia.bs224, in which the variables X, Z, U and R 6 each have the 15 meanings mentioned in rows 1 to 224 of Table 2: CI x II / \ c C Cl a.b 5 20 Zv N 0 N
L
02
C
2 H ~UR 25 Preference is furthermore given to the compounds Ib.b 5 1 to Ib.b 5 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CO
2
C
2
H
5 30 N C1 x Z N ' C1 bb 0 N N 35 UR' Preference is furthermore given to the compounds Ia.b 6 1 to Ia.b 6 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 40 45 90 CI x III Ia.b 6 5 Z N O N LN
UR
6 10 Preference is furthermore given to the compounds Ib.b 6 1 to Ib.b 6 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: CN 15 N C Z N,'C C lb.be x o N 20 UR 6 Preference is furthermore given to the compounds Ia.b 7 1 to Ia.b 7 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 25 CI x IIC Z N la.b 7 30 UR6 O6
NHCO
2
CH
3 Preference is furthermore given to the compounds Ib.b 7 1 to 35 Ib.b 7 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
O.C'NHCO
2
CH
3 1CC N CI 40 Z N /lb.b7 C C1 O N UR' 45 91 Preference is furthermore given to the compounds Ia.b 8 l to Ia.b 8 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: C1 5 X Ia.b8 Z N0 N 10 UR" 0
NHSO
2
CH
3 Preference is furthermore given to the compounds Ib.b 8 l to Ib.b 8 224, in which the variables X, Z, U and R 6 each have the 15 meanings mentioned in rows 1 to 224 of Table 2: 0'-. NHSO 2
CH
3 C Z.N N C \ C Ib.b 8 20 Il _ x O N
UR
6 25 Preference is furthermore given to the compounds Ia.b 9 1 to Ia.b 9 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: F x 30 11 /\C .C, - 1 la.b9 Z N O N 0 2
CH
3
U
6 UR 35 Preference is furthermore given to the compounds Ib.b 9 1 to Ib.b 9 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 40 45 92
CO
2 CH3 r IN F NC C b.b 9 5 1 x O N
UR
6 10 Preference is furthermore given to the compounds Ia.b 10 1 to Ia.b 1 0 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: F x 15 C1 ~~ la.b'O Z N OzN uO 2
C
2
H
5 U UR 20 Preference is furthermore given to the compounds Ib.bll to Ib.b' 0 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 25
CO
2
C
2
H
5 N F Z~. N / C Ib.b1o x 30 0 N
UR
6 Preference is furthermore given to the compounds Ia.bill to 35 Ia.bil224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: F x 40 ['^ ' ' la.b1 Z N UR 45 93 Preference is furthermore given to the compounds Ib.b 11 1 to Ib.b 11 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: CN N Z C /\C1 Ibb" x 10 Y 10 UR Preference is furthermore given to the compounds Ia.b 12 1 to Ia.b 1 2 224, in which the variables X, Z, U and R 6 each have the 15 meanings mentioned in rows 1 to 224 of Table 2: F x C1 -- 1 Ia.b12 20 Z N O N HO Y UR 25 Preference is furthermore given to the compounds Ib.b 12 1 to Ib.b 12 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: CHO I F 30 F Z.- N, C CI Ib.b12 OI N x 35 UR' Preference is furthermore given to the compounds Ia.bI 3 1 to Ia.b 1 3 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 40 45 94 F x - Ia.b13 5 Z N O N UR O''
NHCO
2
CH
3 10 Preference is furthermore given to the compounds Ib.b' 3 1 to Ib.b 1 3 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 15 O NHCO2CH3 TI F Z N,'' CIb.b13 x 20 0 N UR Preference is furthermore given to the compounds Ia.bl 4 1 to 25 Ia.b 1 4 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: F x II W C1 30 ZIa.b 14 O N
UR
6 O ' NHSO 2
CH
3 35 Preference is furthermore given to the compounds Ib.bl 4 1 to Ib.b 1 4 224, in which the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2: 40 45 95 OC' NHSO 2
CH
3 F ZNI /\ Ib.b'4 5 Z N,C C1 x 0 zN
UR
6 10 Furthermore, preference is given to the compounds Ia.bi 5 to 281 to Ia.b 1 5 to 28224 which differ from the compounds Ia.bl to 141 to Ia.bl to 14224 only in that Y is S: 15 x W / \
R
4 I C,:1 la.b15to2 8 Z N S N H Y 6 20 UR and the compounds Ib.b 1 5 to 281 to Ib.bi 5 to 28224 which differ from the compounds Ia.b 1 5 to 281 to Ia.b 1 5 to 28224 only in that the N 25 substituents are inverted: R N Z N,C R 4 Ib.b15to28 30 1 S N Y6
UR
6 35 Moreover, particular preference is given to the substituted ureas of the formula Ia.cl x R 3 II 40 C4 4 0C \ R la.cl O N,' NY UR 45 96 in particular to the compounds listed in Table 3 below: Table 3 5 No. Z X R R 3
R
4 Y U R 6 Ia.cl 1 0 S H H Cl 0 - H Ia.cl 2 0 S H H Cl 0 - CH 3 Ia.cl 3 0 S H H Cl 0 - C 2
H
5 10 Ia.cl 4 0 S H H Cl 0 - n-C 3
H
7 Ia.cl 5 0 S H H Cl 0 - i-C 3
H
7 Ia.cl 6 0 S H H Cl 0 - cyclopropyl Ia.cl 7 0 S H H Cl 0 - n-C 4 H9 Ia.cl 8 0 S H H Cl 0 - sec-C 4
H
9 Ia.cl 9 0 S H H Cl 0 - i-C 4
H
9 Ia.cl 10 0 S H H Cl 0 - t-C 4 H9 Ia.cl 11 0 S H H Cl 0 CH 2 cyclopropyl Ia.cl 12 0 S H H Cl 0 - cyclopentyl 20 Ia.cl 13 0 S H H Cl 0 - cyclohexyl Ia.cl 14 0 S H H Cl 0 - oxiran-2-yl Ia.cl 15 0 S H H Cl 0 - oxetan-2-yl Ia.cl 16 0 S H H Cl 0 - tetrahydrofuran-2-yl 25 Ia.c 1 17 0 S H H Cl 0 - tetrahydropyran-2-yl Ia.cl 18 0 S H H Cl 0 - oxepan-2-yl Ia.cl 19 0 S H H Cl 0 - thiiran-2-yl Ia.cl 20 0 S H H Cl 0 - thietan-2-yl 30 Ia.cl 21 0 S H H Cl 0 - tetrahydrothiofuran-2-yl Ia.cl 22 0 S H H Cl 0 - tetrahydrothiopyran-2-yl Ia.cl 23 0 S H H Cl 0 - thiepan-2-yl Ia.cl 24 0 S H H Cl 0 - oxetan-3-yl Ia.cl 25 0 S H H Cl 0 - tetrahydrofuran-3-yl 35 Ia.cl 26 0 S H H Cl 0 - tetrahydropyran-3-yl Ia.cl 27 0 S H H Cl 0 - oxepan-3-yl Ia.c 1 28 0 S H H Cl 0 - thiethan-3-yl Ia.cl 29 0 S H H Cl 0 - tetrahydrothiofuran-3-yl 40 Ia.cl 30 0 S H H Cl 0 - tetrahydrothiopyran-3-yl Ia.cl 31 0 S H H Cl 0 - thiepan-3-yl Ia.cl 32 0 S H H Cl 0 - tetrahydropyran-4-yl Ia.cl 33 0 S H H Cl 0 - oxepan-4-yl 45 Ia.cl 34 0 S H H Cl 0 - tetrahydrothiopyran-4-yl Ia.cl 35 0 S H H Cl 0 - oxepan-4-yl ia.cl 36 - S H H Cl O - tetrahydrothiopyran-4-yl 36f C- SI..~iE 97 No. Z X R R 3
R
4 Y U R 6 Ia.cl 37 0 S H H Cl 0 0 CH 3 Ia.cl 38 0 S H H Cl 0 0 C 2
H
5 5 Ia.cl 39 0 S H H Cl 0 0 n-C 3
H
7 Ia.c 1 40 0 S H H Cl 0 0 i-C 3
H
7 Ia.cl 41 0 S H H Cl 0 0 cyclopropyl Ia.cl 42 0 S H H Cl 0 - CO 2 H Ia.cl 43 0 S H H Cl 0 - CO 2
CH
3 10- - Ia.cl 44 0 S H H Cl 0 - CO 2
C
2
H
5 Ia.cl 45 0 S H H Cl 0 - CH 2
CO
2
CH
3 Ia.cl 46 0 S H H Cl 0 - CH(CH 3
)CO
2
CH
3 Ia.cl 47 0 S H H Cl 0 0 CH 2
CO
2
CH
3 15 Ia.cl 48 0 S H H Cl 0 0 CH(CH 3
)CO
2
CH
3 Ia.cl 49 0 S H H Cl 0 - Cl Ia.cl 50 0 S H H Cl 0 - CN Ia.cl 51 0 S H H Cl 0 - CH 2 C=CH 20 Ia.cl 52 0 S H H Cl 0 0 CH 2 C=CH Ia.cl 53 0 S H H Cl 0 - CH 2 0CH 3 Ia.cl 54 0 S H H Cl 0 - CH 2
CH
2 0CH 3 Ia.cl 55 0 S H H Cl 0 0 CH 2
CH
2 0CH 3 2 Ia.cl 56 0 S H H Cl 0 CH 2 cyclopentyl 30 35 40 45 98 Moreover, preference is given to the compounds Ib.c 1 l to Ib.c 1 56 which differ from the compounds Ia.cl [sic] to Ia.c 1 56 only in that the N substituents are inverted: 5 R R Z N~ C R 4 - Ib.cl x N 0 10
UR
6 Moreover, preference is given to the compounds Ia.c 2 1 to Ia.c 2 56 which differ from the compounds Ia.cl [sic] to Ia.c 1 56 only in 15 that R is CO 2
CH
3 : x 11 / "- C Ia.c 2 N NNO0 20 LQCH 3
Y
6 20 2C URS Moreover, preference is given to the compounds Ib.c 2 1 to Ib.c 2 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that the N substituents are inverted and R is CO 2
CH
3 : 25 CO 2
CH
3 Z .N / CI Ib.c2 x 30 N 0
UR
6 Moreover, preference is given to the compounds Ia.c 3 1 to Ia.c 3 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that R 35 is CO 2
CH
3 and R 3 is Cl: CI x II c Ia.c 3 40 Z N O
O
2
CH
3 UR Moreover, preference is given to the compounds Ib.c 3 1 to Ib.c 3 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that the 45 N substituents are inverted and R is CO 2
CH
3 and R 3 is Cl: 99 CO 2 CH 1 Cl rI ci Zl. ,N, CA Cl Ib.c3 5 X N O
UR
6 Moreover, preference is given to the compounds Ia.c 4 1 to Ia.c 4 56 10 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that R is C0 2
C
2
H
5 and R 3 is Cl: C1 x CI N"- Ia.c4 15 laic 5 Z N NO
UR
6 Moreover, preference is given to the compounds Ib.c 4 1 to Ib.c 4 56 20 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is Cl: CO2 C 2H C1 Nj 22 25 ZN . N C / \CI Ib.c4 11 x N O Y6
UR
6 30 Moreover, preference is given to the compounds Ia.c 5 1 to Ia.c 5 56 which differ from the compounds Ia.ci 1 to Ia.c 1 56 only in that R is C(O)NHCO 2
CH
3 and R 3 is Cl: C x 35 ,8 C1 N N O Ia.c 5 UR' 40 O 'NHCO2CH U Moreover, preference is given to the compounds Ib.c 5 1 to Ib.c 5 56 which differ from the compounds Ia.cIl to Ia.c 1 56 only in that the N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is Cl: 45 100 OC' NHCO 2
CH
3 NIJ CI Z NNCA -CI lb.cs 11 5 NNO
UR
6 10 Moreover, preference is given to the compounds Ia.c 6 1 to Ia.c 6 56 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that R is C(O)NHSO 2
CH
3 and R 3 is Cl: CC x 15 N C N N 0 Ia.c& URS O
NHSO
2
CH
3 20 Moreover, preference is given to the compounds Ib.c 6 1 to Ib.c 6 56 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is Cl: 0, CNHSO 2
CH
3 NC3 25 N C1 ZlN,'C I(C1 Ib.c6 11 x 30 Y
UR
6 Moreover, preference is given to the compounds Ia.c 7 1 to Ia.c 7 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that R 35 is CO 2
CH
3 and
R
3 is F: F X C1 Z N NO Ia.c 7 40
O
2
CH
3
Y
6 UR Moreover, preference is given to the compounds Ib.c 7 1 to Ib.c 7 56 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that the 45 N substituents are inverted and R is CO 2
CH
3 and R 3 is F: 101 CO 2 CH F Z NC CI Ib.c 7 5 X N O Y
UR
6 Moreover, preference is given to the compounds Ia.c 8 1 to Ia.c 8 56 10 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that R is C0 2
C
2
H
5 and R 3 is F: F x 15 CI Z N N O Ia.c
O
2
C
2 H UR UR Moreover, preference is given to the compounds Ib.c 8 1 to Ib.c 8 56 20 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is F:
CO
2
C
2
H
5 N1 F 25 \N CI Ib.c8 x N O
UR
6 30 Moreover, preference is given to the compounds Ia.c 9 1 to Ia.c 9 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that R is C(O)NHCO 2
CH
3 and R 3 is F: F x 35 IC N NO Ia.c Y
UR
6 40 0 NHCO 2
CH
3 Moreover, preference is given to the compounds Ib.c 9 1 to Ib.c 9 56 which differ from the compounds Ia.c 1 l to Ia.c 1 56 only in that the N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is F: 45 102 O.C' NHCO 2 CH, N' F Z NK , / \ C1 Ib.c9 xI - 5~ O1 x
UR
6 10 Moreover, preference is given to the compounds Ia.c 10 1 to Ia.c 1 0 56 which differ from the compounds Ia.cil to Ia.c 1 56 only in that R is C(O)NHSO 2
CH
3 and R 3 is F: F X 1C1 15 - NN O la.clo URS O NHSO2CH U 20 Moreover, preference is given to the compounds Ib.cil1 to Ib.c 11 56 which differ from the compounds Ia.c 1 1 to Ia.c 1 56 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is F: O*-C'NHSO2 CH 3 25 N F Z N / C Ib.c11 x NN 0 30 UR Moreover, preference is given to the compounds Ia.c 1 2 to 221 to Ia.c12 to 2256 which differ from the compounds Ia.cl to 111 to Ia.cl 35 to 1156 only in that Y is S: 3R5 R 3 Z N, R N S a.c12 to 22 40
UR
6 Moreover, preference is given to the compounds Ib.c 1 2 to 221 to Ib.c 12 to 2256 which differ from the compounds Ia.cl to 111 to Ia.cl 45 to 1156 only in that the N substituents are inverted and Y is S: 103 R R3 Z N R 4 Ib.c12 to 22 11 x 5 N S Y6
UR
6 Moreover, preference is given to the compounds Ia.c 2 3 to 331 to Ia.c23 to 3356 which differ from the compounds Ia.cl to 111 to Ia.cl 10 to 1156 only in that X is 0: R 3 0 NR 15 Z N,R N S Ia.c 2 a to a UR6 Moreover, preference is given to the compounds Ib.c 2 3 to 331 to Ib.c 2 3 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 0: R 3 Z N
R
4 lb.c23to33 25 N S
UR
6 Moreover, preference is given to the compounds Ia.c 3 4 to 441 to 30 Ia.c 3 4 to 4456 which differ from the compounds Ia.cl to 111 to Ia.cl to 1156 only in that Z is S: R3 O 1/ \ R4 N" 35 S N,'R N 1a.ca4to44 Y6 UR* Moreover, preference is given to the compounds Ib.c 3 4 to 441 to 40 Ib.c 3 4 to 4456 which differ from the compounds Ia.cl to 111 to Ia.cl to 1156 only in that the N substituents are inverted and Z is S: 45 104 R 3 S N - / \ R 4 lb.c34to44 11 0 5 NN S
UR
6 Moreover, particular preference is given to the substituted ureas 10 of the formula Ia.dl R 3 x N' ''N la.d1 15 Z R N,'R in particular to the compounds listed in Table 4 below: 20 Table 4 No. Z X R R 3 Y T R7 Ia.dl 1 0 S H H 0 - CH 3 Ia.dl 2 0 S H H 0 - C 2
H
5 25 Ia.dl 3 0 S H H 0 - n-C 3
H
7 Ia.dl 4 0 S H H 0 - cyclopropyl Ia.dl 5 0 S H H 0 - n-C 4 H9 Ia.dl 6 0 S H H 0 - sec-C 4
H
9 30 Ia.dl 7 0 S H H 0 - t-C 4
H
9 Ia.dl 8 0 S H H 0 - CH 2
-CH=CH
2 Ia.dl 9 0 S H H 0 - CH 2 -C-=CH Ia.dl 10 0 S H H 0 - CH 2
CH
2 Cl 35 Ia.dl 11 0 S H H 0 - CH 2
CH
2 0CH 3 Ia.dl 12 0 S H H 0 - CH 2
CH
2 CN Ia.dl 13 0 S H H 0 - H Ia.dl 14 0 S H H 0 0 H Ia.dl 15 0 S H H 0 0 CH 3 40 Ia.dl 16 0 S H H 0 0 C 2
H
5 Ia.dl 17 0 S H H 0 0 n-C 3
H
7 Ia.dl 18 0 S H H 0 0 cyclopropyl Ia.dl 19 0 S H H 0 0 n-C 4
H
9 45 Ia.dl 20 0 S H H 0 0 sec-C 4 Hg Ia.dl 21 0 S H H 0 0 t-C 4
H
9 105 No. Z X R R3 Y T R7 Ia.dl 22 0 S H H 0 0 CH 2
-CH=CH
2 Ia.dl 23 0 S H H 0 O CH2-C=CH 5 Ia.dl 24 0 S H H O O CH2CH2Cl Ia.dl 25 0 S H H 0 0 CH 2
CH
2 0CH 3 Ia.dl 26 0 S H H 0 0 CH 2
CH
2 CN Ia.dl 27 0 S H H 0 0 i-C 3
H
7 Ia.dl 28 0 S H H 0 0 i-C 4 H9 Ia.dl 29 0 S H H 0 - i-C 3
H
7 Ia.dl 30 0 S H H 0 - i-C 4 H9 Ia.dl 31 0 S H H 0 0 CH 2
CO
2
CH
3 Ia.dl 32 0 S H H 0 0 CH(CH 3
)CO
2
CH
3 15 Ia.dl 33 0 S H H 0 0 CH(CH 3
)CO
2
C
2
H
5 Ia.dl 34 0 S H H 0 - CH 2
CO
2
CH
3 Ia.dl 35 0 S H H 0 - CH 2
CO
2 -n-C 3
H
7 20 Moreover, preference is given to the compounds Ib.dll to Ib.d 1 35 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that the N substituents are inverted: R 3 25 z NC Y i_ Ib.di x /74O TR 0 30 Moreover, preference is given to the compounds Ia.d 2 1 to Ia.d 2 35 which differ from the compounds Ia.dil to Ia.dl35 only in that R is CO 2
CH
3 :
R
3 x 35 Y Ia.& Z
CNCO
2
CH
3 , 4 40 Moreover, preference is given to the compounds Ib.d 2 1 to Ib.d 2 35 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that the N substituents are inverted and R is CO 2
CH
3 : 45 106 CO 2 CH N RS z N' 5|| \ Ib.d2 5 X /7 0 Moreover, preference is given to the compounds Ia.d 3 1 to Ia.d 3 35 10 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is CO 2
CH
3 and R 3 is Cl: CI x II N- Ia.d 3 15 Z N,C2C TR Moreover, preference is given to the compounds Ib.d 3 1 to Ib.d 3 35 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that the 20 N substituents are inverted and R is CO 2
CH
3 and R 3 is Cl: CO2
CH
3 C1 N CI z NC( Y 25 |C - Ib.d Moreover, preference is given to the compounds Ia.d 4 1 to Ia.d 4 35 30 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is C0 2
C
2
H
5 and R 3 is Cl: CI x II / \ 35 C Y Ia.d4 35 N V CO2C2H 2 570 Moreover, preference is given to the compounds Ib.d 4 l to Ib.d 4 35 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is Cl: 45 107
CO
2
C
2 H 1C5 N Cl I z N,' C Y 5 1| Ib.d4 x Moreover, preference is given to the compounds Ia.d 5 1 to Ia.d 5 35 10 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is C(O)NHCO 2
CH
3 and R 3 is Cl: C1 x II C - lad 5 15 Z N O; NHCO2CH 3 Moreover, preference is given to the compounds Ib.d 5 1 to Ib.d 5 35 20 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that the N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is Cl:
O,,NHCO
2 CH N CI 25 / \ Ib.d5 NC Y lbd x TR7 30 Moreover, preference is given to the compounds Ia.d 6 1 to Ia.d 6 35 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is C(O)NHSO 2
CH
3 and R 3 is Cl: CI x 35 N- / \ Y N a.d 6 Z N /R7 O'
'NHSO
2
CH
3 40 Moreover, preference is given to the compounds Ib.d 6 1 to Ib.d 6 35 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is Cl: 45 108 OC 'NHSO 2 CH 1 C1 z N C Y lb.d6 5 ||1 X R/74 TR 0 Moreover, preference is given to the compounds Ia.d 7 1 to Ia.d 7 35 10 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is CO 2
CH
3 and R 3 is F: F x 15 Ca.d 7 15 j Z N CO 2
CH
3 7 0 Moreover, preference is given to the compounds Ib.d 7 1 to Ib.d 7 35 20 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that the N substituents are inverted and R is C02CH 3 and R 3 is F: CO 2CH 3 12 N F 25 z NC Y || _ b.d7 I7 O 30 Moreover, preference is given to the compounds Ia.d 8 1 to Ia.d 8 35 which differ from the compounds Ia.d 1 l to Ia.dl 35 only in that R is C0 2
C
2
H
5 and R 3 is F: F x 35 C Y Ia.d8 3N 4i N CO2C2H 5 Moreover, preference is given to the compounds Ib.d 8 l to Ib.d 8 35 40 which differ from the compounds Ia.d 1 l to Ia.dl 35 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is F: 45 109 C0 2
C
2
H
5 N4 F z N,'C Y 5 lb.d8 x Moreover, preference is given to the compounds Ia.d 9 1 to Ia.d 9 35 10 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that R is C(O)NHCH 2
CH
3 and R 3 is F: F x II / N Ia.d 9 15 Z N N7 O
NHCO
2
CH
3 Moreover, preference is given to the compounds Ib.d 9 1 to Ib.d 9 35 20 which differ from the compounds Ia.d 1 l to Ia.d 1 35 only in that the N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is F: 0'. NHCO 2
CH
3 5 F 25r I z N,.C / Y Ib.d9 I7 O 30 Moreover, preference is given to the compounds Ia.d 10 1 to Ia.d 1 0 35 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that R is C(0)NHSO 2
CH
3 and R 3 is F: F x 35 \\ / \ CY Ia.d1O Z N z7 O 0,;' NHSO 2
CH
3 40 Moreover, preference is given to the compounds Ib.d 9 1 to Ib.d 9 35 which differ from the compounds Ia.d 1 1 to Ia.d 1 35 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is F: 45 110 0C 'NHSO 2
CH
3 N F z NCA Y Ib.d1O 5 ||1 x /74 TR Moreover, preference is given to the compounds Ia.dill to Ia.dIl35 10 which differ from the compounds Ia.dl 1 to Ia.dl 35 only in that R is CO 2
CH
3 , R 3 is F and Y is S: F x III~l 15" ' la.d11 15 N 7 Z"-"N COJH TR 70 Moreover, preference is given to the compounds Ib.dill to Ib.dIl35 20 which differ from the compounds Ia.dll to Ia.d 1 35 only in that the N substituents are inverted and R is CO 2
CH
3 , R 3 is F and Y is S: COpH 3 N F 25 z ,C S || Ib.d" X 30 Moreover, preference is given to the compounds Ia.d 1 2 to 221 to Ia.d 1 2 to 2235 which differ from the compounds Ia.dl to 111 to Ia.dl to 1135 only in that X is 0: R 3 Y 35 - Ia.d12to22 Z
-
N, R/ TR7 O Moreover, preference is given to the compounds Ib.d1 2 to 221 to 40 Ib.d' 2 to 2235 which differ from the compounds Ia.d 1 to 111 to Ia.dl to 1135 only in that the N substituents are inverted and X is 0: 45 111 R 3 R C Y | _ Ib.d12 to 22 0 7 0 Moreover, preference is given to the compounds Ia.d 2 3 to 331 to Ia.d 2 3 to 3335 which differ from the compounds Ia.di to 111 to Ia.dl 10 to 1135 only in that Z is S:
R
3 xy N - Ia.d23tos3 S N R 15 Moreover, preference is given to the compounds Ib.d 2 3 to 331 to Ib.d 2 3 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: 20 R R C" Y || _ \ b.d23toss x 25 T/R O Moreover, particular preference is given to the substituted ureas of the formula Ia.el 30 R 3 x C Y la.el Z NR /N7
TR
7 35 in particular to the compounds listed in Table 5 below: Table 5 40 No. Z X R R3 Y T R7 Ia.el 1 0 S H H 0 - CH 3 Ia.el 2 0 S H H 0 - C 2
H
5 Ia.el 3 0 S H H 0 - n-C 3
H
7 45 Ia.el 4 0 S H H 0 - cyclopropyl Ia.el 5 0 S H H 0 - n-C 4 H9 Ia.el 6 0 S H H 0 - sec-C 4 H9 112 No. Z X R R3 Y T R 7 Ia.el 7 0 S H H 0 - t-C 4 H9 Ia.el 8 0 S H H 0 - CH 2
-CH=CH
2 5 Ia.el 9 0 S H H 0 - CH 2 -C=CH Ia.el 10 0 S H H 0 - CH 2
CH
2 Cl Ia.el 11 0 S H H 0 - CH 2
CH
2 0CH 3 Ia.el 12 0 S H H 0 - CH 2
CH
2 CN Ia.el 13 0 S H H 0 - H 10 Ia.el 14 0 S H H 0 0 H Ia.el 15 0 S H H 0 0 CH 3 Ia.el 16 0 S H H 0 0 C 2
H
5 Ia.el 17 0 S H H 0 0 n-C 3
H
7 15 Ia.el 18 0 S H H 0 0 cyclopropyl Ia.el 19 0 S H H 0 0 n-C 4
H
9 Ia.el 20 0 S H H 0 0 sec-C 4
H
9 Ia.el 21 0 S H H 0 0 t-C 4
H
9 20 Ia.el 22 0 S H H 0 0 CH 2
-CH=CH
2 Ia.el 23 0 S H H 0 0 CH 2 -CwCH Ia.el 24 0 S H H 0 0 CH 2
CH
2 Cl Ia.el 25 0 S H H 0 0 CH 2
CH
2 0CH 3 25 Ia.el 26 0 S H H 0 0 CH 2
CH
2 CN Ia.el 27 0 S H H 0 0 i-C 3
H
7 Ia.el 28 0 S H H 0 0 i-C 4
H
9 Ia.el 29 0 S H H 0 - i-C3H7 Ia.el 30 0 S H H 0 - i-C 4 H9 30 Ia.el 31 0 S H H 0 0 CH 2
CO
2
CH
3 Ia.el 32 0 S H H 0 0 CH(CH 3
)CO
2
CH
3 Ia.el 33 0 S H H 0 0 CH(CH 3
)CO
2
C
2
H
5 Ia.el 34 0 S H H 0 - CH 2
CO
2
CH
3 35 Ia.el 35 0 S H H 0 - CH 2
CO
2 -n-C 3
H
7 Moreover, preference is given to the compounds Ib.ell to Ib.e 1 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the 40 N substituents are inverted: R 3 z N C ||Ib.e x N' 45 / O
TR
113 Moreover, preference is given to the compounds Ia.e 2 1 to Ia.e 2 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R is CO 2
CH
3 : Ra3 5 X II / \ i. C1N N la.e2
CO
2
CH
3 / 7 O TR 10 Moreover, preference is given to the compounds Ib.e 2 1 to Ib.e 2 35 which differ from the compounds Ia.ell to Ia.el35 only in that the N substituents are inverted and R is CO 2
CH
3 :
CO
2 CH z N C || Ib.e2 Z~, ~ / 7R TR~ 20 Moreover, preference is given to the compounds Ia.e 3 1 to Ia.e 3 35 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that R is CO 2
CH
3 and R 3 is Cl: CI X 25 111 C Ia.e 3 Z CO2 CH3 / 7 TR 30 Moreover, preference is given to the compounds Ib.e 3 1 to Ib.e 3 35 which differ from the compounds Ia.el 1 to Ia.el 35 only in that the N substituents are inverted and R is CO 2
CH
3 and R 3 is Cl:
CO
2
CH
3 35 N Cl NC 1 / Ib.e 3 / 7 TR 40 Moreover, preference is given to the compounds Ia.e 4 1 to Ia.e 4 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R is C0 2
C
2
H
5 and R 3 is Cl: 45 114 CI x N
.
Ia.e 4 Z~ N N Nz 0 5 Z CO 2
C
2
H
5 / O TR Moreover, preference is given to the compounds Ib.e 4 l to Ib.e 4 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is Cl: 10 CO 22H5 122 N CI || __ b.e4 15 N T1R Moreover, preference is given to the compounds Ia.e 5 1 to Ia.e 5 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R 20 is C(O)NHCO 2
CH
3 and R 3 is Cl: CI x II / C, _ Ia.es -C-,.O Z N N O 25 R O "NHCO 2
CH
3 Moreover, preference is given to the compounds Ib.e 5 1 to Ib.e 5 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the 30 N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is Cl: 0.C NHCO 2 CH N CI 35 z N,'C y( Ib.e 5 I I / 7 TR Moreover, preference is given to the compounds Ia.e 6 1 to Ia.e 6 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R is C(O)NHSO 2
CH
3 and R 3 is Cl: 45 115 CI x /I\ "C / Ia.e 6 Z N N' O1 5 TR7 O1 NHSO 2
CH
3 Moreover, preference is given to the compounds Ib.e 6 1 to Ib.e 6 35 10 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is Cl: O. C NHSO 2
CH
3 C1 3 N CI 15 Z.' N- N CA \ Ib.e 6 / 7 TR 20 Moreover, preference is given to the compounds Ia.e 7 1 to Ia.e 7 35 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that R is CO 2
CH
3 and R 3 is F: F x 25 Ia.e 7 CO2 CH 3 O TR Moreover, preference is given to the compounds Ib.e 7 1 to Ib.e 7 35 30 which differ from the compounds Ia.e 1 l to Ia.el35 only in that the N substituents are inverted and R is CO 2
CH
3 and R 3 is F:
CO
2
CH
3 N F 35 Ib.e7 N> O TR Moreover, preference is given to the compounds Ia.e 8 l to Ia.e 8 35 40 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R is C0 2
C
2
H
5 and R 3 is F: 45 116 F x N / \Ia.e 8 I
I
Z NCO 2
C
2 H O TR Moreover, preference is given to the compounds Ib.e 8 l to Ib.e 8 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is F: 10 CO 2C2H Nj F z NC' || Ib.es 15 N O / 7 TR Moreover, preference is given to the compounds Ia.e 9 1 to Ia.e 9 35 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that R 20 is C(O)NHCO 2
CH
3 and R 3 is F: F x 11 N .la.e 9 Z N N O 25R 0 NHCO 2
CH
3 Moreover, preference is given to the compounds Ib.e 9 1 to Ib.e 9 35 which differ from the compounds Ia.ell to Ia.e 1 35 only in that the 30 N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is F: O.
,NHCO
2
CH
3 IF N F 35 z N,C'' y Ib.e 9 x N' N 7 TR Moreover, preference is given to the compounds Ia.e 1 0 1 to Ia.e 1 0 35 40 which differ from the compounds Ia.ell to Ia.e 1 35 only in that R is C(O)NHSO 2
CH
3 and R 3 is F: 45 117 F x C la.elo z N NO 5 TR7 Ol NHSO2CH 3 Moreover, preference is given to the compounds Ib.e 10 1 to Ib.e 10 35 10 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is F: OC /NHSO 2 CH NI F 15 z NC / \ Ib.e1O / 7 TR 20 Moreover, preference is given to the compounds Ia.e 1 1 l to Ia.e 11 35 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that R is CO 2
CH
3 , R 3 is F and Y is S: F x II / \ 25 N"C,' - la.e 1 1 ZyCO2CH3 1O TR Moreover, preference is given to the compounds Ib.elll to Ib.ell35 30 which differ from the compounds Ia.el 1 to Ia.e 1 35 only in that the N substituents are inverted and R is CO 2
CH
3 , R 3 is F and Y is S:
CO
2
CH
3 N F 35 z N,'C 11 ._ /lb.ell ITR x Nk Moreover, preference is given to the compounds Ia.e 1 2 to 221 to 40 Ia.e 1 2 to 2235 which differ from the compounds Ia.ei to 111 to Ia.el to 1135 only in that X is 0: 45 118
R
3 0 II
-
fIa.e12 to 22 5Z N R /N O
TR
7 Moreover, preference is given to the compounds Ia.e 1 2 to 221 to Ia.e12 to 2235 which differ from the compounds Ia.ei to 111 to Ia.e 1 to 1135 only in that the N substituents are inverted and X is 0: 10 "R R 3 z NN C 11 Ib.e12 to22 x Nk'0 N O 15 TR Moreover, preference is given to the compounds Ia.e 2 3 to 331 to Ia.e 2 3 to 3335 which differ from the compounds Ia.e 1 to 111 to Ia.e 1 to 1135 only in that Z is S: 20 R3 xY -- N Ia.e 2 to 3 3 V- 'R 4R O
T
1 R 25 Moreover, preference is given to the compounds Ia.e 2 3 to 331 to Ia.e23 to 3335 which differ from the compounds Ia.ei to 111 to Ia.el to 1135 only in that the N substituents are inverted and Z is S: N"RR 3 30 R R N C || Ib.e23to33 TR 35 Moreover, particular preference is given to the substituted ureas of the formula Ia.fl
R
3 x 40 1 / \ 4 SN - Ia.fl Z N R O 0
R
9
R
8 45 in particular to the compounds listed in Table 6 below: 119 Table 6 No. Z X R R 3 R4 R8 R9 Ia.f 1 l 0 S H H Cl H H 5 Ia.f12 0 S H H Cl H CH 3 Ia.f 1 3 0 S H H Cl H C 2
H
5 Ia.f 1 4 0 S H H Cl H n-C 3
H
7 Ia.f 1 5 0 S H H Cl H i-C 3
H
7 10 Ia.f 1 6 0 S H H Cl H n-C 4 H9 Ia.f 1 7 0 S H H Cl cyclopropyl H Ia.f 1 8 0 S H H Cl CH 3 H Ia.f 1 9 0 S H H Cl CH 3
CH
3 15 Ia.f 1 10 0 S H H Cl C 2
H
5 H Ia.f 1 11 0 S H H Cl C 2
H
5
CH
3 Ia.f 1 12 0 S H H Cl n-C 3
H
7
C
2
H
5 Ia.f 1 13 0 S H H Cl n-C 3
H
7 n-C 3
H
7 Ia.f 1 14 0 S H H Cl Cl H 20 Ia.f 1 15 0 S H H Cl H Cl Ia.f 1 16 0 S H H Cl Cl CH 3 Ia.f 1 17 0 S H H Cl ------ C(O) ---- Ia.f 1 18 0 S H H Cl CH 3
CH
2
CH
2 Cl 25 Ia.f 1 19 0 S H H Cl C 2
H
5
C
2
H
5 Ia.f 1 20 0 S H H Cl i-C 3
H
7 i-C 3
H
7 Ia.fl21 0 S H H Cl i-C 3
H
7 H 30 Moreover, preference is given to the compounds Ib.f 1 l to Ib.fl21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that the N substituents are inverted: R R3 35 z N C R4 x ~- Ib.f' 0 R' R 40 Moreover, preference is given to the compounds Ia.f 2 1 to Ia.f 2 21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that R is CO 2
CH
3 : 45 120
R
3 x |I / \ R 4 N R Ia.f2 5 Z NCO 2
CH
3 0 R9 Re Moreover, preference is given to the compounds Ib.f 2 1 to Ib.f 2 21 10 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that the N substituents are inverted and R is CO 2
CH
3 : CO 2CH, 123 N
R
3 15 1il Ib.f2 x 0 R R 20 Moreover, preference is given to the compounds Ia.f 3 1 to Ia.f 3 21 which differ from the compounds Ia.f 1 1 to Ia.f 1 21 only in that R is CO 2
CH
3 and R 3 is Cl: C x 25 I / \ R 4 N - _a.f3 Z N,'C0 2 CH 3 R R 30 Moreover, preference is given to the compounds Ib.f 3 1 to Ib.f 3 21 which differ from the compounds Ia.f 1 1 to Ia.fl21 only in that the N substituents are inverted and R is CO 2
CH
3 and R 3 is Cl: CO 2CH 3 35 N C NC R 4 ||RIb.f3 0 40 0 Moreover, preference is given to the compounds Ia.f 4 1 to Ia.f 4 21 which differ from the compounds Ia.f 1 1 to Ia.fl21 only in that R 45 is C0 2
C
2
H
5 and R 3 is Cl: 121 CI x S/ \ R 4 N , Ia.f 4
NCO
2
C
2 H, 0
R
9
R
8 Moreover, preference is given to the compounds Ib.f 4 1 to Ib.f 4 21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that the 10 N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is Cl:
CO
2
C
2 H, N C1 Z 'C / R 4 15 - Ib.f4 x 0 0
R
9
R
8 20 Moreover, preference is given to the compounds Ia.f 5 1 to Ia.f 5 21 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that R is C(0)NHCO 2
CH
3 and R 3 is Cl: CI X 25 R4 la.fs Zl--N O 0 !R RS 30 0 NHCO 2
CH
3 Moreover, preference is given to the compounds Ib.f 5 1 to Ib.f 5 21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that the N substituents are inverted and R is C(0)NHCO 2
CH
3 and R 3 is Cl: 35 O, NHCO 2
CH
3 C1 N CI Z NA \ R 4 Ib.f5 11 40 x 0 R R 8 Moreover, preference is given to the compounds Ia.f 6 1 to Ia.f 6 21 45 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that R is C(O)NHSO 2
CH
3 and R 3 is Cl: 122 CI x C -- la.fe 5 0 0
'NHSO
2
CH
3 10 Moreover, preference is given to the compounds Ib.f 6 1 to Ib.f 6 21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is Cl: OC 'NHSO 2 CH 15 N C1 Z15NC \ R 4 lb.fO 11 x 0 20 R9 Re Moreover, preference is given to the compounds Ia.f 7 1 to Ia.f 7 21 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that R is CO 2
CH
3 and R 3 is F: 25 F x N R a.f7
N,CO
2 CH 0 30 0 R9 Re Moreover, preference is given to the compounds Ib.f 7 1 to Ib.f 7 21 which differ from the compounds Ia.f 1 l to Ia.fl21 only in that the N substituents are inverted and R is CO 2
CH
3 and R 3 is F:
CO
2
CH
3 N F 1 _ Ib.f7 40 x0 0
R
9
R
8 Moreover, preference is given to the compounds Ia.f 8 1 to Ia.f 8 21 45 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that R is C0 2
C
2
H
5 and R 3 is F: 123 F x II / \ R 4 N _.. la.fs 5 Z N,CO 2C2 H, O R9 R Moreover, preference is given to the compounds Ib.f 8 1 to Ib.f 8 21 10 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that the N substituents are inverted and R is C0 2
C
2
H
5 and R 3 is F:
CO
2
C
2 H Nj F Z5N ,'C \ R 4 15 l1 - lb.f8 x 0 200 20 Moreover, preference is given to the compounds Ia.f 9 1 to Ia.f 9 21 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that R is C(O)NHCO 2
CH
3 and R 3 is F: F x I I x/ 25 N R4 IN.- Ia.f Z N 0 O R" Ra 30 0C, NHCO 2
CH
3 Moreover, preference is given to the compounds Ib.f 9 1 to Ib.f 9 21 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that the N substituents are inverted and R is C(O)NHCO 2
CH
3 and R 3 is F: 35 01C'.NHCO2CH3 N F Z \ R 4 lb.f9 if x 40 0 0 R R Moreover, preference is given to the compounds Ia.fl 0 1 to Ia.f 1 0 21 45 which differ from the compounds Ia.f 1 l to Ia.f 1 21 only in that R is C(0)NHSO 2
CH
3 and R 3 is F: 124 F xR Ia.flO 5 0 R' R' O 'NHSO 2CH 3 10 Moreover, preference is given to the compounds Ib.f1 0 1 to Ib.f 10 21 which differ from the compounds Ia.f 1 l to Ia.fi21 only in that the N substituents are inverted and R is C(O)NHSO 2
CH
3 and R 3 is F: 0 CNHSO 2 CH 15 F Z N C R4 Ib.fPO 11 x 0 200 20 R" Re Moreover, preference is given to the compounds Ia.f 1 1 to 201 to Ia.f 1 1 to 2021 which differ from the compounds Ia.fl to 101 to Ia.fl to 1021 only in that X is 0: 25
R
3 III / \ 4 NC - la.f1 to 20 Z N1 N, 0 30 0 R9 R' Moreover, preference is given to the compounds Ib.f 1 1 to 201 to Ib.f 1 1 to 2021 which differ from the compounds Ia.fl to 101 to Ia.fi 35 t 1021 only in that the N substituents are inverted and X is 0: N R 3 R R Z N C R 4 I b.fl1to20 0 0 40 R 9" R 8 Moreover, preference is given to the compounds Ia.f 21 to 301 to Ia.f 21 to 3021 which differ from the compounds Ia.fl to 101 to Ia.fl 45 to 1021 only in that Z is S: 125
R
3 x II\ 4 ||/ \ R 4 N R la.f21 to 3o CN 5 R 0
R
9
R
8 Moreover, preference is given to the compounds Ib.f 2 1 to 301 to 10 Ib.f21 to 3021 which differ from the compounds Ia.fi to 101 to Ia.fi to 1021 only in that the N substituents are inverted and Z is S: R F S N,'CA \1 R 4 lb.f21 to ao 15 x 0
R
9
R
8 20 25 30 35 40 45 126 To prepare the compounds of the formula Ia according to the invention where Z = 0, it is possible, for example, to react the N-(2-hydroxyethyl)-N-amino-N'-acylureas known from WO 94/10173 5 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 10 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. 15 Scheme 1 0 o I I ~.c .Q HCH I8 -Q H NH 2 H N 20 0 H+Q N NH (or (I a, R =H) 25 e.g.802) SO NH Compounds of the formula Ia where R = hydrogen can be prepared by 30 reacting 1H,2H-perhydrodiazines of the formula IIa (R = H) with an isocyanate (X = 0) 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. 35 Scheme 2 X NH N NHQ | I + X=C=N-Q Z I N Z NR Z N' R 40 Ha II la Analogously, it is also possible to react N-substituted 45 perhydrodiazines IIb with an isocyanate or isothiocyanate III to give the end products IIb according to the following scheme: 127 Scheme 2a Il N + X=C=N-Q Z N NN 5 (RA)m R(m R li b IiI lb 10 According to a further process, shown in scheme 3, substituted triazolinediones (X = 0) or -thiones (X = S) of the formula IV can be ring-opened with an alkoxide or thiolate to give the substituted ureas Ib(1) (R = C(X)YR 1 0 where X = 0 or S and Y = 0 or S). 15 Scheme 3 x NZ NIX 'NI-f Q I N-Q + -YR1O Do.0 (RA)m N(RA)m N C(X)YR1o 20 IV V lb In a corresponding manner, it is possible to prepare the 25 substituted ureas Ib( 2 ) (R = C(O)NRilR1 2 ) according to the invention by the process shown in scheme 3a, starting from substituted triazolinediones (X = 0) or -thiones (X = S) of the formula IV by reaction with a basic amine VI. Scheme 3a 30 11 Z N Z N' C'NHQ I N-Q + HNR11 R12 -b KN N C(O)NR11 R12 (RA)m (RA)m 35 IV VI Ib 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 40 substituted carbonyl isocyanate VIIIa or sulfonyl isocyanate VIIIb to give the substituted ureas Ia( 3 ) (where R = C(O)NHVC1) or Ia( 4 ) (where R = C(O)NHWR1 2 '). 45 128 Scheme 4 X X=C=NVCI (RA)m 11 Q + Vila V=CO W r I 5Z -1-N,C ,NHVCl 5 ') X Vil b V= S0 2 (RA)M 11Q N 'C NH I a(3) C'H xa 10 I a X=C=NWR12' (RA)m + Villa W=CO - i (R=H)2 Z N,CNHWR12' Vill b W = SO 2 2 0 Vill c W = S 3 Ia( 4 ) 15 It is possible to prepare the substituted ureas Ia (R * H) according to the process shown in scheme 5, starting with ureas 20 of the formula Ia' (R = H), by reaction with an acid derivative IX in which A is a leaving group. Scheme 5 X x || (RA)m Ii (RA)M 11 "C Q 25 'Q R-A N NI Zl N,H R Ia'(R= H) ix la 30 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)YR10, CO 2 H or CHO, to give the ureas Ib' 35 where R = H. From these, it is then possible to prepare the substituted ureas where R = C(X)YR10, CHO, CN, C(X)NRilR 1 2 , C(O)R 2 , P(O)(ORI)Rl, P(O)(ORI) 2 , S(O)R 1 , S(0) 2
R
1 or S(0) 2 NHR1 by reaction with an acid derivative R-A in which R is as defined above and A is a nucleophilically displaceable leaving group. 40 45 129 Scheme 6 X X || 11 Z N C'NHQ H20 Z N C'NHQ R -ROH H 5 (RA)m (RA)m lb Ib (R=H) 10 X X || II Z N'C NHQ + R-A s Z N'C NHQ (RA)m H(RA)m R 15 1b' (R=H) IX lb The schemes 4 to 6 above also apply in an analogous manner to the 20 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 25 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 30 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 35 pentane, hexane, heptane, cyclohexane, aromatic compounds, for example benzene, toluene, xylene, heteroaromatic compounds, for examle pyridine, ap,y-picoline and quinoline, chlorinated hydrocarbons, for example methylene chloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, 40 1,1-dichloroethylene, chlorobenzene, 1,2-, 1,3-, 1,4-dichlorobenzene, 1-chloronaphthalene and 1,2,4-trichlorobenzene, ethers, such as 1,4-dioxane, anisole, glycol ethers, such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters, such as ethyl 45 acetate, propyl acetate, methyl isobutyrate, isobutyl acetate, carboxamides, such as DMF, N-methylpyrrolidone, nitrated hydrocarbons, such as nitromethane, nitroethane, nitropropdne nd 130 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, 5 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 10 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 15 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 * H) and water and of urea Ib' (R = H) and the acid radical IX can likewise be carried out under the molar ratios mentioned. 20 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. 25 The concentrations of the starting materials in the solvent are generally from 0.1 to 5 mol/l, preferably from 0.2 to 2 mol/l. The reaction sequence illustrated in scheme 1 is described in more detail below. 30 The reaction of the N-amino-N'-arylureas according to scheme 1 with formaldehyde or paraformaldehyde is advantageously carried out in the presence of a solvent at 0 to 150 0 C, preferably 10 to 100 0 C, particularly preferably 20 to 600C. Aqueous formaldehyde, 35 preferably as an about 37% strength solution, is advantageously added at 10 to 25 0 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 0 C for the reaction to go to 40 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 45 water of reaction; however, the water of reaction can also be removed during the reaction via a water separator. The reaction with formaldehyde according LO step I in scheme 1 is preferably 131 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 5 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. 10 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 15 of the abovementioned solvents, at from 0 to 1500C, preferably 10 to 1200C, particularly preferably 20 to 800C. The acid used can be an aromatic sulfonic acid, for example benzenesulfonic acid, p-chloro- [sic] or p-toluenesulfonic acid, 20 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 25 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 30 25 0 C and over 2 to 20 min to the organic acid, preferably acetic acid, as reaction medium, and stirring is continued at 20 to 800C 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 35 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. 40 The concentration of the starting materials in the solvent is generally from 0.1 to 5 mol/l, preferably from 0.2 to 2 mol/l. Instead of an acid, it is also possible to use, as catalyst, a neutral or acidic surface-active metal oxide, for example 45 aluminum oxide, iron oxide, boron oxide, silicon dioxide, 132 titanium dioxide, arsenic oxide, antimony oxide, chromium oxide or manganese oxide. The reaction can be carried out under atmospheric pressure or 5 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). 10 Scheme la x 0 0 "COChP" 15 N -H I a' (R = H) IV 20 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 (ClC(=o)OCC1 3 ), advantageously in the presence of one of the abovementioned anhydrous solvents, at from -10 to 25 1200C, preferably from 0 to 800C, particularly preferably from 10 to 600C. The phosgene is advantageously introduced at 10 to 600C and with stirring into a mixture of a 30 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. 35 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 10% by weight, based on the starting material. The basic catalyst used can also be an organic base, such as 40 triethylamine, tri-n-propylamine, N,N-dimethylaniline 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 45 diphosgene is advantageously added with stirring, at from 0 to -50C and over a period of 2 to 20 min, to the mixture of the starting material and one of the abovementioned solvents", if- 133 appropriate with addition of activated carbon, DMF or the organic base, and the mixture is allowed to warm to 100C over a period of 1 hour and then stirred at 10 to 600C for another 1 to 12 hours. The molar amount of phosgene or diphosgene is 0.98 to 5, 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/l, preferably from 0.2 to 2 mol/l. 10 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 15 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 20 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 25 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 30 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 35 more detail below. In the reactions according to the invention, an isocyanate or isothiocyanate III is advantageously added at 10 to 25 0 C and over a period of 5 to 30 min to a mixture of the perhydrodiazine IIa 40 or IIb in one of the abovementioned solvents, and the mixture is then stirred at 20 to 80 0 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 N-substituted perhydrodiazines (R * H), it is also possible to initially charge the isocyanate or 45 isothiocyanate III in one of the abovementioned solvents, to add 134 the N-substituted perhydrodiazine and then to complete the reaction as above. In the ring opening of the triazolinedione IV with the 5 nucleophiles V and VI according to schemes 3 and 3a, the nucleophile is advantageously added at 10 to 300C 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 0 C for 0.5 to 24 hours, preferably for 1 to 10 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. 15 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, 20 tri-n-propylamine, N-ethyldiisopropylamine, pyridine, a-, -, 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 25 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 30 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 35 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, 40 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 45 urea Ia' or Ib' where R = H in one of the abovementioned solvents, at 10 to 300C, and the mixture is then stirred for 135 another 0.5 to 24 hours, preferably 1 to 10 hours, at 20 to 120 0 C for the reaction to go to completion. However, it is also possible to add the substituted urea Ia or Ib 5 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 10 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. 15 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 20 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. 25 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 Ia' (where R = H) to base. 30 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 35 salts. Suitable compounds which may be mentioned are: tetraalkyl-(Ci-C18) -ammonium chlorides, bromides or fluorides, N-benzyltrialkyl-( CI-C 1 8 )-ammonium chlorides, bromides or fluorides, tetraalkyl-(Ci-Ci 8 )-phosphonium chlorides or bromides, tetraphenylphosphonium chloride or bromide, 40 (phenyl)o(alkyl-(Ci-Ci 8 ))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-transfer catalyst is generally up to 20% by weight, preferably between 1 45 and 15% by weight and particularly preferably between 2 and 8% by weight, based on the acid derivative IX.
136 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(O)R 2 , it is an oxy-Ci-C 6 -alkanoyl, oxy-C 3
-C
6 -alkenoyl or oxy-C 3
-C
6 -alkynoyl radical, and in the case 5 of formyl, it is an oxy-Ci-C 6 -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)OR
10 , C(S)OR 10 , C(S)SR 1 o, C(O)SR 1 0, CO 2 H or CHO (urea Ib 10 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 1000C, advantageously from 20 to 800C. Thus, the substituted urea Ib(l) is initially charged in one of the abovementioned solvents, for example water, the base is then 15 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 20 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. 25 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 30 of the abovementioned solvents, at from 10 to 300C, advantageously in the presence of a base, and the mixture is then stirred at 20 to 1200C for another 0.5 to 24 hours, preferably 1 to 10 hours, for the reaction to go to completion. 35 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). 40 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 Ia and Ib from similar substituted ureas Ia and Ib which differ in the meaning 45 of one radical.
137 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 5 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 10 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 15 (RA)m NH (X) HZ NH 2 20 in which Z is 0 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 25 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 = 0 or S, which are, if appropriate, in the case that Z = S, oxidized in a further 30 reaction step to give the sulfoxides Z = SO or sulfones Z = S02, or the radicals R are derivatized. Examples of suitable nucleophilically displaceable leaving groups are halogen, preferably chlorine or bromine, Ci-C 6 -alkoxy, such as 35 methoxy, ethoxy, n-propoxy, n-butoxy, Ci-C 4 -haloalkoxy, such as trichloromethoxy, trifluoromethoxy, pentafluoroethoxy, N-bonded heterocyclyl, such as imidazolyl, Ci-C 6 -alkylcarbonyloxy (or Ci-C 6 -alkanoate), such as acetate, propionate, n-butyrate, isobutyrate, pivalate and caproate, Cl-C6-haloalkylcarbonyloxy, 40 such as mono-, di- and trichloroacetate, Ci-C 6 -alkylsulfonyloxy, such as methylsulfonyloxy, Ci-C 6 -haloalkylsulfonyloxy, such as trifluoromethylsulfonyloxy, phenylsulfonyloxy, where the phenyl radical may, if appropriate, be mono- or disubstituted by halogen or Ci-C 6 -alkyl, such as phenylsulfonyloxy, p-toluenesulfonyloxy 45 and p-Cl-phenylsulfonyloxy, N-bonded nitrogen-C 5
-C
6 -heterocyclyl, such as N-imidazolyl.
138 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 5 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 10 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 15 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. 20 N HIN - CO 2 CH 3 NIIC 2 CH 3 25 + COACH + HCHO CO2C a OH NH 2 CI OH NH2 H 30 Preferred embodiments of the process are mentioned below: The first reaction step is explained in more detail below: The 35 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 0 C, preferably from -10 to 800C, particularly preferably from 0 to 600C. 40 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-tetrachloroethane, chlorobenzene, 45 1,2-, 1,3- or 1,4-dichlorobenzene, ethers, such as 1,4-dioxane, anisole, glycol ethers, such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters, such as 139 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, 5 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. 10 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 15 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 20 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, 25 pyridine, a-, P-, 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 30 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. 35 Advantageously, the acid derivative IX is added, at 0 to 600C 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 600C is continued 40 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 45 the phase-transfer catalyst in the two phases, and the reaction 140 can then be completed in the temperature range mentioned by adding base. The reaction can be carried out under atmospheric pressure or 5 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 accumulated in the filtrate. 10 The second reaction step iq explained below: the hydrazides are subsequently reacted, advantageously under acidic conditions, with a formaldehyde solution or paraformaldehyde in one of the abovementioned solvents. 15 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 20 materials in the solvent is 0.1 to 5 mol/l, preferably 0.2 to 2 mol/l. The acid used can be an aromatic sulfonic acid, for example benzenesulfonic acid, p-chloro- [sic] or p-toluenesulfonic acid, 25 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 30 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 35 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 40 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 0 C, advantageously 10 to 800C, particularly preferably 20 to 50 0 C, and stirring is continued at 40 to 500C for 10 to 50 hours, preferably 15 to 30 hours, to bring the reaction to completion. 45 141 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 5 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 10 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 15 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 20 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 25 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 30 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. 35 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 40 hydrocarbons, such as methylene chloride or 1,2-dichloroethane. Also very suitable for oxidizing the thiols to sulfoxides or sulfones are chlorine and bromine. This oxidation is expediently carried out in polar solvents, such as water, acetonitrile, 45 dioxane, or in two-phase systems, such as aqueous potassium bicarbonate solution/dichloromethane, and also acetic acid. It is furthermore possible to employ as sources of active halogen 142 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. 5 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 10 Methylene Blue. Suitable inert solvents are hydrocarbons, such as pentane, hexane, heptane, cyclohexane, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, 15 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 20 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, 25 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 = SO 2 ) are obtained, depending on the stoichiometry of the 30 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 35 oxidation to the sulfone. The concentration of the starting materials in the solvent is generally 0.1 to 5 mol/l, preferably 0.2 to 2 mol/l. 40 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 abovementioned catalysts, in one of the abovementioned solvents, and then to add the oxidizing agent over a period of 0.25 to 20 hours with stirring. The addition and the 45 reaction temperature depends on the optimum efficiency of the oxidizing agent in question and on avoiding side reactions. If -photosensitized oxygen is used, -he reaction is generally carried 143 out at from -20 to 800C; however, if metal catalysis is employed, the reaction is generally carried out at from 50 to 1400C, and if ozone is used, the reaction is generally carried out at from -78 to 600C. Owing to the limited solubility of the oxygen 5 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 10 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 15 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 0 to 900C, with tert-butyl pypochlorite [sic), the reaction is generally carried out at from -78 to 300C, and with N-halo compounds 20 generally at from 0 to 300C. In the case of chlorine or bromine, a reaction temperature of from 0 to 400C is recommended. The oxidations can be carried out under atmospheric pressure or under superatmospheric pressure, continuously or batchwise. 25 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 = SO2) 30 Accordingly, the reaction product Ia is, if appropriate, allowed to cool to from 90 to 200C, 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 35 sodium hypochlorite. For work-up of the oxidation mixture, the end products IIa are generally taken up in a water-immiscible solvent, acidic impurities and/or oxidizing agents are extracted using dilute 40 alkali or water, the mixture is dried and the solvent is removed under reduced pressure. 45 144 I. Preparation of the starting compounds Methyl tetrahydro-N-(2,4-dichloro-5-methoxyiminomethylphenyl) 4H-1,3,4-oxdiazine-3-thiocarboxamide-4-carboxylate [sic] 5 a) Methyl N-amino-N-2-hydroxyethylcarbamate At from 0 to 50C, 248.4 g (2.628 mol) of methyl chloroformate were added with stirring, in the course of 30 min, to a mixture 10 of 200 g (2.628 mol) of 2-hydrazionethanol [sic] and 266 g (2.628 mol) of triethylamine in 1600 ml of methylene chloride. The mixture was stirred at from 3 to 220C for 3 h, and the precipitated hydrochloride was then filtered off with suction and washed with THF, and the filtrate was concentrated under reduced 15 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 20 GC, the purity was 85.2%. 1 H-NMR (400 MHZ, d 6 -DMSO) 8(ppm): 4.4 - 4.8 (broad/3H) NH 2 /OH; 3.6 (s/3H) CH 3 0; 3.52 (t/2H) and 3.35 (t/2H) CH 2
-CH
2 25 b) Methyl tetrahydro-4H-1,3,4-oxdiazine-4-carboxylate [sic] 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 30 chloride. 8.5 g (0.045 mol) of p-toluenesulfonic acid were added, and the mixture was then stirred at 420C for 21 h, until the precipitate had dissolved. The mixture was cooled to 200C, magnesium sulfate was added, the mixture was filtered and the filtrate was concentrated under reduced pressure. This gave 35 111.8 g of the title compound as a colorless resin of a GC purity of 85%, corresponding to a yield of 85.8% of theory. 1 H-NMR (500 MHZ, CF 3
CO
2 D) 8(ppm): 5.09 (s/2H) CH 2 ; 4.02 (s/3H)
CH
3 0; 3.8 - 4.25 (m/4H) CH 2
CH
2 40 IR v (cm- 1 ): C=O 1703 The intermediates of the formulae IIb and X listed in Tables a) and b) below were prepared in a similar manner. 45 145 Table a) 5 HO(CH 2
)
2 N-R N (X)
NH
2 10 Compound X R nD 2 3 V [Cm-1] Yield No. [%] 1 CO 2
CH
3 - - 98.9 2 C0 2
C
2
H
5 C=O 1695 cm- 1 , 88 15
NH
2 3336 cm- 1 3 C(O)SCH 3 1.5458 85 4 C(O)SC 2
H
5 1.5345 86 5 C0 2 -i-C 3
H
7 C=O 1694 cm- 1 , 69
NH
2 3338 cm- 1 20 6 C0 2 -t-C 4
H
9 7 CO 2 -phenyl 8 C0 2 -p-Cl-phenyl 9 C0 2 -benzyl 1.5442 C=O 1706 cm- 1 , 62
NH
2 3336 cm- 1 25 10 C(S)OCH 3 11 C0 2 -n-CBH 1 7 12 CO 2
CH
2
CH
2 Cl 1.4988 C=O 1706 cm- 1 65 13 C0 2 -cyclopentyl 1.4981 C=O 1695 cm- 1 50 30 14 C0 2 -n-C 14
H
19 C=0 1700 cm- 1 88 15 COCH 3 1.4938 22 nD 23 = refractive index at 234C v = [ cm-1] IR bands 35 Table b) R 40 N 1 ~ (11b) N H 45 146 Com- R nD 2 3 V [cm- 1 ] 1 H-NMR Yield pound b.p. [*C/mbar] [6 (ppm)] 1%] IIb m.p. [*CJ No. 5 1 CO 2
CH
3 - - see above 85.5 2 C0 2
C
2
H
5 100-105/0.5 C=0: 1701 4.05 78 (q/2H),
O-CH
2 -C; 1.18 (t/3H) 10
CH
3 3 C(O)SCH 3 103-111/0.4 C=0: 1659 75 1.5542 4 C(O)SC 2
H
5 1.5428 C=0: 1657 74 5 C0 2 -i-C 3
H
7 C=0: 1702 61 15 6 C0 2 -t-C 4
H
9 7 CO 2 -phenyl 8 CO 2 -p-Cl-phenyl 9 C0 2 -benzyl 7.4-7.24 43 20 (m, 5H) 5.1 (s,2H) 10
C(S)OCH
3 11 C0 2 -n-C 8
H
1 7 25 12 CO 2
CH
2
CH
2 Cl 1.5130 C=O 1709 53 13 C0 2 -cyclopentyl 145-150/0.5 C=O 1700 51 14 C0 2 -n-C 1 4
H
2 9 77-81 59 15 COCH 3 C=O 1683 34 30 nD 2 3 = refractive index at 23 0 C m.p. = melting point b.p. = boiling point at the stated pressure II. Preparation of the compounds Ia and Ib 35 Example 1 (compound Ib, No. 1, Table 7) Methyl tetrahydro-N-(2,4-dichloro-5-methoxyiminomethyl phenyl)-4H-1,3,4-oxdiazine-3-thiocarboxamide-4-carboxylate [sic] 40 Over the course of 5 min, 9.11 g (0.035 mol) of 2,4-dichloro-5-methoxyiminomethylphenyl isothiocyanate were added with stirring to 10.22 g (0.07 mol) of the compound from Ib in 150 ml of tetrahydrofuran, and the mixture was stirred at 22 0 C for 45 5 h and then at 40 to 50 0 C for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in 147 methylene chloride and fractionated over silica gel. This gave 11.9 g (78% of theory) of the title compound of m.p. 80-830C. IR v (cm-1): C=O/C=S 1733, 1705 5 Example 2 (compound Ib.2, Table 7) Tetrahydro-N-(4-chloro-5-methoxyiminomethylphenyl)-4H-1,3,4 oxdiazine-3-carboxamide [sic] 10 6.3 g (17.66 mmol) of methyl tetrahydro-N-(4-chloro-5-methoxy iminomethylphenyl)-4H-1,3,4-oxdiazine-3-carboxamide-4-carboxylate [sic] 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 15 hydroxide in 50 ml of water was then added with stirring at 60 to 700C. 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 IN hydrochloric acid, which resulted in evolution 20 of gas with formation of foam and precipitation. The resulting mixture was extracted three times with methylene chloride. The combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure. This gave 4.9 g (83.6% of theory) of the title compound as a colorless resin. 25 1 H-NMR (400 MHZ d 6 -DMSO) 8 (ppm): 8.4 (s/lH) CH=N; 8.2 (s/lH), 7.7 (m/1H), 7.36 (m/1H) phenyl; 4.0 (s/3H) N=OCH 3 IR v (cm-1): C=O 1681 30 Example 3 (compound Ib.3, Table 7) Methyl tetrahydro-N-(2,4-dichloro-5-methoxyphenyl)-4H-1,3,4 oxdiazine-3-carboxamide-4-carboxylate [sic] 35 With stirring, 0.3 g (1.666 mmol) of 30% strength sodium methoxide was added to a solution of 0.5 g (1.505 mmol) of 8-(2',4'-dichloro-5'-methyloxyphenyl)-4-oxa-7,9-dioxo-1,2,8 triaza(4.3.0)nonane [sic] in 50 ml of methanol. The mixture was 40 stirred at 22 0 C for another 6 h. The reaction mixture was concentrated under reduced pressure and partitioned between methylene chloride and iN hydrochloric acid. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure, giving 0.5 g (88.5% of theory) of the title compound as 45 colorless crystals of m.p. 160-1630C.
148 IR v (cm-1): C=O 1730, 1693 Example 4 (compound Ib.5, Table 7) 5 Ethyl tetrahydro-N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4H 1,3,4-oxdiazine-3-thiocarboxamide-4-carboxylate [sic] With stirring, 0.17 g (2.473 mmol) of sodium ethoxide was added to a solution of 0.8 g (2.249 mmol) of 10 8-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4-oxa-7-oxo-9 thioxo-1,2,8-triaza(4.3.0)nonane [sic] in a mixture of 30 ml of ethanol and 30 ml of methylene chloride, and the mixture was stirred at 22 0 C for 1 h. 100 ml of methylene chloride were then added, and the mixture was extracted 2 x with IN hydrochloric 15 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. 143-1450C. 20 Example 5 (compound Ib.95, Table 7) Tetrahydro-N-(4'-chloro-2'-fluoro-5'-propargyloxyphe nyl)-4H-1,3,4-oxdiazine-3-thiocarboxamide-4-(N'-methoxycarbo nyl)carboxamide [sic] 25 At 22 0 C, 0.22 g of methoxycarbonyl isocyanate (90% pure) was added to a solution of 0.6 g of tetrahydro-N-(4'-chloro-2'-fluoro 5'-propargyloxyphenyl)-4H-1,3,4-oxdiazine-3-thiocarboxamite [sic] (compound Ib, No. 5 of Table 7, prepared by hydrolysis of 30 compound Ib.4 (Table 7, Example 4), by the method given in Example 2, and the mixture was stirred for 22 h. The mixture was concentrated under reduced pressure and the residue was digested with ether and filtered off with suction, giving 0.6 g of the title compound of melting point 195*C. 35 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. 40 Table 7 (compounds Ib No.1 to No. 101 where Q = Q-1 and Z = 0) 45 149 ~RR 5 O b x 10 No. R X R 3
R
4
R
5 m.p.: [ 0 C] or IR: v [cm- 1 ] 1 CO 2
CH
3 S Cl Cl CH=NOCH 3 80 - 830C 15 2 H 0 H Cl CH=NOCH 3 1681 3 CO 2
CH
3 0 Cl Cl OCH 3 160 - 1630C 4 CO 2
CH
3 S F Cl OCH 2 C=CH 156 - 160 0 C 5 H S F Cl OCH 2 C=CH 124 - 128 0 C 20 6 CO 2
CH
3 S F Cl O-C(=CH 2
)CO
2
CH
3 68 - 71 0 C 7 CO 2
CH
3 S F Cl CH=NOCH 3 150 - 1530C 8 CO 2
CH
3 0 F Cl CO-0-C(CH 3
)
3 60 - 650C 9 C0 2
CH
3 0 H Cl CH=NOCH 3 153 - 1550C 10 CO 2
CH
3 0 F Cl OCH 2 C=CH 130 0 C 25 11 C0 2
C
2
H
5 S F Cl OCH 2 C=CH 143 - 145 0 C 12 C0 2
C
2
H
5 0 F Cl OCH 2 C=CH 13 C0 2 -iC 3
H
7 S F Cl OCH 2 C=CH 118 - 123 0 C 14 C0 2 -iC 3
H
7 0 F Cl OCH 2 C-=CH 30 15 C0 2 -nC 3
H
7 0 F Cl OCH 2 C=CH 16 C0 2 -nC 3
H
7 S F Cl OCH 2 C=CH 17 CO 2
CH
3 S Cl Cl OCH 2 C=-CH 141 - 1430C 18 C0 2
CH
3 0 Cl Cl OCH 2 C=-CH 35 19 CO 2
CH
3 S H Cl OCH 2 C=CH 20 CO 2
CH
3 0 H Cl OCH 2 C-=CH 21 C0 2
CH
3 S H Cl OCH 2
CO
2
CH
3 22 CO 2
CH
3 0 H Cl OCH 2
CO
2
CH
3 40 23 CO 2
CH
3 S Cl Cl OCH 2
CO
2
CH
3 24 CO 2
CH
3 0 Cl Cl OCH 2
CO
2
CH
3 25 CO 2
CH
3 S F Cl OCH 2
CO
2
CH
3 142 0 C 26 C0 2
CH
3 0 F Cl OCH 2
CO
2
CH
3 27 CO 2
CH
3 S F Cl OCH 2
CO
2 -nC 5 Hii 45 150 No. R X R 3
R
4
R
5 m.p.: [0C] or IR: V [cm- 1 ] 28 CO 2
CH
3 0 F Cl OCH 2
CO
2 -nC 5 Hii 5 29 CO 2
CH
3 S Cl Cl SCH 2
CO
2
CH
3 30 CO 2
CH
3 0 Cl Cl SCH 2
CO
2
CH
3 31 CO 2
CH
3 S F Cl SCH 2
CO
2
CH
3 129 - 1320C 32 CO 2
CH
3 0 F Cl SCH 2
CO
2
CH
3 1737,1701 cm- 1 33 CO 2
CH
3 S H Cl OCH(CH 3
)CO
2
CH
3 10 3 CO 2
CH
3 0 H Cl OCH(CH 3
)CO
2
CH
3 35 CO 2
CH
3 S Cl Cl OCH(CH 3
)CO
2
CH
3 36 CO 2
CH
3 0 Cl Cl OCH(CH 3
)CO
2
CH
3 37 CO 2
CH
3 S F Cl OCH(CH 3
)CO
2
CH
3 73 - 760C 15 38 CO 2
CH
3 0 F Cl OCH(CH 3
)CO
2
CH
3 39 CO 2
CH
3 S F Cl SCH(CH 3
)CO
2
CH
3 1735 cm- 1 40 CO 2
CH
3 0 F Cl SCH(CH 3
)CO
2
CH
3 41 C0 2
CH
3 S H Cl CO 2
CH
3 20 42 C0 2
CH
3 0 H Cl CO 2
CH
3 43 CO2CH 3 S Cl Cl CO 2
CH
3 44 C0 2
CH
3 0 Cl Cl CO 2
CH
3 45 CO 2
CH
3 S F Cl CO 2
CH
3 185 - 1870C 46 CO 2
CH
3 0 F Cl CO 2
CH
3 25 47 CO 2
CH
3 S H Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 48 CO 2
CH
3 0 H Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 49 CO 2
CH
3 S Cl Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 50 CO 2
CH
3 0 Cl Cl C0 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 30 51 CO 2
CH
3 S F Cl C0 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 52 CO 2
CH
3 0 F Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 53 CO 2
CH
3 S F Cl CO 2
CH
2
CH
2
OCH
3 54 CO 2
CH
3 0 F Cl CO 2
CH
2
CH
2 0CH 3 35 55 CO 2
CH
3 S F Cl C(=NOCH 3
)OCH
3 56 CO 2
CH
3 0 F Cl C(=NOCH 3
)OCH
3 57 CO 2
CH
3 S F Cl C(=NOCH 3
)OCH
2
CO
2
CH
3 58 CO 2
CH
3 0 F Cl C(=NOCH 3
)OCH
2
CO
2
CH
3 40 59 CO 2
CH
3 S F Cl C(O)N(CH 3
)OCH
3 60 CO 2
CH
3 0 F Cl C(O)N(CH 3
)OCH
3 61 CO 2
CH
3 S Cl Cl CH=NOCH 3 62 CO 2
CH
3 0 F Cl CH=NOCH 3 63 CO 2
CH
3 S F Cl CH=NOCH 3 150 - 153 0 C 64 CO 2
CH
3 0 F Cl CH=NOC 2
H
5 151 No. R X R 3
R
4
R
5 m.p.: [0C] or IR: V [cm-1] 65 C0 2
CH
3 S F Cl CH=NOC 2
H
5 5 66 CO 2
CH
3 0 F Cl CH=NOCH 2
CO
2
CH
3 67 C0 2
CH
3 S F Cl CH=NOCH 2
CO
2
CH
3 68 CO 2
CH
3 0 F Cl CH=NOCH(CH 3
)CO
2
CH
3 69 CO 2
CH
3 S F Cl CH=NOCH(CH 3
)CO
2
CH
3 70 CO 2
CH
3 0 F Cl CH=C(Cl)CO 2
C
2
H
5 10 71 CO 2
CH
3 S F Cl CH=C(Cl)C0 2
C
2
H
5 72 CO 2
CH
3 0 F Cl CH 2 -CH(Cl)CO 2
C
2
H
5 73 CO 2
CH
3 S F Cl CH 2 -CH(Cl)CO 2
C
2
H
5 74 CO 2
CH
3 0 F Cl CH=NOCH 2 C=CH 15 75 CO 2
CH
3 S F Cl CH=NOCH 2 C=-CH 76 C(O)NHCO 2 Et S F Cl 0-cyclopentyl 1950C decomp. 77 CO 2 Et S F Cl OCH 2
CH=CH
2 118 - 1220C 78 CO 2
CH
3 S F Cl OCH 2
CH=CH
2 158 - 159 0 C 20 79 C0 2 -iC 3
H
7 S F Cl OCH 2
CH=CH
2 139 - 140 0 C 80 H S F Cl 0-cyclopentyl 115 - 118 0 C 81 CO 2
CH
3 S F Cl 0-cyclopentyl 177 - 1790C 82 H S Cl Cl CO 2 H 168-1700C decomp. 25 83 CO 2 Et 0 F Cl OCH 3 56 - 58 0 C 84 C(O)NHCO 2 Et 0 H Cl CH=NOCH 3 214-2150C decomp. 85 C0 2 -iC 3
H
7 S Cl Cl CN 140 - 1430C 30 86 C0 2
C
2
H
5 S F Cl CO 2
CH
3 160 - 163 0 C 87 C(0)NHCO 2
CH
3 S F Cl 0-cyclopentyl 190 0 C decomp. 88 C(0)NHCO 2
C
2
H
5 S F Cl OCH 2 C=CH 172 - 1740C 89 C0 2 -benzyl S F Cl OCH 2 C=CH 49 - 510C 35 90 C0 2 -cyclo- S F Cl OCH 2 C=CH 114 - 1160C pentyl 91 C0 2
-CH
2
CH
2 Cl S F Cl OCH 2 C=CH 1730 cm- 1 92 C0 2 -n-C 1 4
H
2 9 S F Cl OCH 2 C=CH 35 - 360C 93 H S F Cl CO 2 H 1600C decomp. 40 94 C(O)NHCO 2
CH
3 S F Cl OCH 2 C=CH 1950C decomp. 95 CO 2
CH
3 S F Cl C0 2 -i-C 3
H
7 149 - 1510C 96 CO 2
CH
3 0 F F H 92 - 930C 97 CO 2
CH
3 0 F F NO 2 1734,1700 cm- 1 45 98 H S F Cl OH 153 - 1560C 99 H S F Cl OCH 2
CO
2
CH
3 1880C 152 No. R X R 3
R
4
R
5 m.p.: [OC] or IR: v (cm-1] 100 CO 2
CH
3 S Cl Cl OCH 3 1730,1704 cm-1 5 101 CO 2
CH
3 S F CN F 175 - 1760C Table 8:(compounds Ia No.1 to No. 94 where Q = Q-1 and Z = 0) X R 10 -a ONIIN 111R F 15 No. R X R 3
R
4
R
5 m.p.: [0C] or IR: v [cm-1] 20 1 CO 2
CH
3 S Cl Cl CH=NOCH 3 2 H 0 H Cl CH=NOCH 3 58 - 600C 3 CO 2
CH
3 0 Cl Cl OCH 3 1746 cm-1 4 CO 2
CH
3 S F Cl OCH 2 C=CH 25 5 H S F Cl OCH 2 CmCH 157 - 1580C 6 CO 2
CH
3 S F Cl 0-C(=CH 2
)CO
2
CH
3 7 CO 2
CH
3 S F Cl CH=NOCH 3 8 CO 2
CH
3 0 F Cl CO-0-C(CH 3
)
3 30 9 CO 2
CH
3 0 H Cl CH=NOCH 3 10 C0 2
CH
3 0 F Cl OCH 2 C=CH 112 - 1150C 11 CO2C 2
H
5 S F Cl OCH 2 CmCH 12 C0 2
C
2
H
5 0 F Cl OCH 2 C=CH 13 C0 2 -iC 3
H
7 S F Cl OCH 2 C=CH 3514 C 2 -iC 3
H
7 F Cl OCH 2 CCH 15 C0 2 -nC 3
H
7 0 F Cl OCH 2 C=CH 16 C0 2 -nC 3
H
7 S F Cl OCH 2 C=CH 17 CO 2
CH
3 S Cl Cl OCH 2 C=CH 40 18 C0 2
CH
3 0 Cl Cl OCH 2 CmCH 19 C0 2
CH
3 S H Cl OCH 2 C=CH 20 CO 2
CH
3 0 H Cl OCH 2 C=CH 21 CO 2
CH
3 S H Cl OCH 2
CO
2
CH
3 4 22 CO 2
CH
3 0 H Cl OCH 2
CO
2
CH
3 23 CO 2
CH
3 S Cl Cl OCH 2
CO
2
CH
3 24 CO 2
CH
3 0 Cl Cl OCH 2
CO
2
CH
3 1 153 No. R X R 3
R
4
R
5 m.p.: [OC] or IR: V [cm-1] 25 CO 2
CH
3 S F Cl OCH 2
CO
2
CH
3 26 CO 2
CH
3 0 F Cl OCH 2
CO
2
CH
3 27 C2CH3 S F Cl OCH2CO2-nC5Hii 28 CO 2
CH
3 O F Cl OCH 2
CO
2 -nC 5 Hii 29 CO 2
CH
3 S Cl Cl SCH 2
CO
2
C
H
3 30 CO 2
CH
3 0 Cl Cl SCH 2
CO
2
CH
3 0 COCH 00lC SH 2 CH-4 10 31 CO 2
CH
3 S F Cl SCH 2
CO
2
CH
3 32 CO 2
CH
3 0 F Cl SCH 2
CO
2
CH
3 33 CO 2
CH
3 S H Cl OCH(CH 3
)CO
2
CH
3 34 CO 2
CH
3 0 H Cl OCH(CH 3
)CO
2
CH
3 15 35 CO 2
CH
3 S Cl Cl OCH(CH 3
)CO
2
CH
3 36 CO 2
CH
3 0 Cl Cl OCH(CH 3
)CO
2
CH
3 37 CO 2
CH
3 S F Cl OCH(CH 3
)CO
2
CH
3 38 CO 2
CH
3 0 F Cl OCH(CH 3
)CO
2
CH
3 20 39 CO 2
CH
3 S F Cl SCH(CH 3
)CO
2
CH
3 40 CO 2
CH
3 0 F Cl SCH(CH 3
)CO
2
CH
3 41 C0 2
CH
3 S H Cl CO 2
CH
3 42 CO 2
CH
3 0 H Cl CO 2
CH
3 43 CO 2
CH
3 S Cl Cl CO 2
CH
3 25 44 CO 2
CH
3 0 Cl Cl C0 2
CH
3 45 CO 2
CH
3 S F Cl CO 2
CH
3 46 CO 2
CH
3 0 F Cl CO 2
CH
3 47 CO 2
CH
3 S H Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 30 48 CO 2
CH
3 0 H Cl C0 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 49 CO 2
CH
3 S Cl Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 50 CO 2
CH
3 0 Cl Cl C0 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 51 C0 2
CH
3 S F Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 35 52 CO 2
CH
3 0 F Cl CO 2
C(CH
3
)
2
CO
2
CH
2
CH=CH
2 53 CO 2
CH
3 S F Cl CO 2
CH
2
CH
2 0CH 3 54 CO 2
CH
3 0 F Cl CO 2
CH
2
CH
2 0CH 3 55 CO 2
CH
3 S F Cl C(=NOCH 3
)OCH
3 40 56 CO 2
CH
3 0 F Cl C(=NOCH 3
)OCH
3 57 CO 2
CH
3 S F Cl C(=NOCH 3
)OCH
2
CO
2
CH
3 58 CO 2
CH
3 0 F Cl C(=NOCH 3
)OCH
2
CO
2
CH
3 59 CO 2
CH
3 S F Cl C(0)N(CH 3
)OCH
3 60 CO 2
CH
3 0 F Cl C(O)N(CH 3
)OCH
3 61 C0 2
CH
3 S Cl Cl CH=NOCH 3 62 C0 2
CH
3 0 F Cl CH=NOCHi 154 No. R X R 3
R
4
R
5 m.p.: [OC] or IR: V [cm-1] 63 CO 2
CH
3 S F Cl CH=NOCH 3 64 CO 2
CH
3 0 F Cl CH=NOC 2
H
5 65 CO 2
CH
3 S F Cl CH=NOC 2
H
5 66 CO 2
CH
3 0 F Cl CH=NOCH 2
CO
2
CH
3 67 CO 2
CH
3 S F Cl CH=NOCH 2
CO
2
CH
3 68 CO 2
CH
3 0 F Cl CH=NOCH(CH 3
)CO
2
CH
3 10 69 CO 2
CH
3 S F Cl CH=NOCH(CH 3
)CO
2
CH
3 70 CO 2
CH
3 0 F Cl CH=C(Cl)C0 2
C
2
H
5 71 CO 2
CH
3 S F Cl CH=C(Cl)C0 2
C
2
H
5 72 CO 2
CH
3 0 F Cl CH 2 -CH(Cl)CO 2
C
2
H
5 15 73 CO 2
CH
3 S F Cl CH 2 -CH(Cl)CO 2
C
2
H
5 74 CO 2
CH
3 0 F Cl CH=NOCH 2 C=CH 75 CO 2
CH
3 S F Cl CH=NOCH 2 C=CH 76 C(O)NHCO 2 Et S F Cl OCH 2 C=CH 175 0 C decomp. 20 77 C(0)NHCO 2 Et 0 F Cl OCH 3 189 - 1900C 78 H 0 Cl Cl OCH 3 128 - 1300C 79 H 0 F Cl OCH 3 147 - 1500C 80 H 0 Cl Cl CH=N-OCH 3 210 - 2130C 81 H 0 F Cl CH=N-OCH 3 170 - 1720C 25 82 C(0)NHCO 2 Et 0 Cl Cl CH=N-OCH 3 1890C 83 C(O)NHCO 2 Et 0 F Cl CH=N-OCH 3 179 - 1800C 84 H S F Cl CH=N-OCH 3 175 - 1760C 85 C(0)NHCO 2 Et S F Cl CH=N-OCH 3 1810C decomp. 30 86 H S F Cl OCH(CH 3
)CO
2
CH
3 (R) 1753 cm- 1 87 C(O)NHCO 2
C
2
H
5 S F Cl OCH(CH 3
)CO
2
CH
3 (R) 158 - 1630C 88 C(0)NHCO 2
CH
3 S F Cl OCH(CH 3
)CO
2
CH
3 (R) 174 - 178 0 C 89 H S F Cl CO 2
CH
3 175 - 1780C 35 90 C(0)NHCO 2
CH
3 S F Cl OCH 2 C=CH 1840C decomp. 91 C(O)NHCO 2
CH
3 S F Cl CO 2
CH
3 160 0 C decomp. 92 C(O)NHCO 2
C
2
H
5 S F Cl CO 2
CH
3 1590C decomp. 93 C(O)NHCO 2
CH
3 0 F Cl CH=N-OCH 3 180-1830C 40 decomp. 94 CO 2
CH
3 0 F Cl OCH 3 61 - 64 0 C Example 6 45 Moreover, the compound of the formula Ib where Z = 0, X = S, m = 0, R = CO 2
CH
3 , where Q is a radical of the formula Q4 where R 3 = F, Y = 0 and Tr 7 = propargyl, was prepared by reacting 7-fluo ro-6-isothiocyanato-4-(2-propargyl)-2H-1,4-benzoxazin-3(4H)-one 155 with methyl tetrahydro-4H-1,3,4-oxdiazine-4-carboxylate [sic]. Melting point 190-193 0 C. Example 7 5 N-[4'-Chloro-2'-fluoro-5-methoxyiminomethylphenyl)-4H-1,3,4-thia diazine-4-carboxamide At 22 0 C, 0.7 g (5.7 mmol) of thionyl chloride was added to a 10 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 0 C for 2 h. After cooling, the mixture was worked up by aqueous extraction 15 giving, after removal of the solvent, 1.3 g of N-methyleneimino N-2-chloroethyl-N'-[4'-chloro-2'-fluoro-5'-(methoxyiminomethyl) phenyl]urea of melting point 120-122'C. 1.2 g of the chloroethyl compound obtained in this manner were 20 reacted with 0.7 g of thiourea in 50 ml of DMSO for 12 h at 22 0 C and for 1 h at 50'C. The reaction mixture was then, at room temperature, stirred into 65 ml of 10% by weight strength aqueous sodium hydroxide solution, and the mixture was stirred at 22-30 0 C for another hour. The temperature was maintained while 75 ml of 25 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. Concentration of the solution gave 0.2 g of the title compound. Melting point 155-162 0 C. 30 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 35 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. 40 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 crops are the following: 45 156 Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, 5 Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), 10 Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, 15 Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia 20 faba, Vitis vinifera and Zea mays. 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. 25 The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with 30 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). 35 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 40 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. 45 157 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 5 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, 10 and water. 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 15 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 20 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. 25 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 30 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 35 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 40 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, 45 such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, less, clay, dolomite, diatomaceous earth, calcium sulfate, mdgnesiumt sulfate, magnesium oxide, giounid 158 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. 5 The concentrations of 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 98% by weight, preferably 0.01 to 95% by weight, of at least one active 10 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 15 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 20 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 25 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 30 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 35 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. 40 III 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 of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica 45 gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of 159 water gives a spray mixture which comprises 0.1% by weight of the active compound. IV 20 parts by weight of the compound Ib.6 are dissolved in 5 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 0 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 10 weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound. V 3 parts by weight of the compound Ib.6 are mixed with 97 15 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 are mixed intimately with 2 parts by weight of the calcium salt of 20 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. 25 VII 1 part by weight of the compound Ib.6 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a 30 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 35 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 40 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, 45 (het)aryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinones,. 2-aruyl-1,3-cyclohexanediones, hetaryl aryl keLones, 160 benzylisoxazolidinones, meta-CF 3 -phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, 5 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 10 acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils. 15 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 20 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, 25 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 30 Use Examples The herbicidal action of the substituted ureas of the formulae Ia and Ib was demonstrated by greenhouse experiments: 35 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 sown separately for each species. 40 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 45 until the plants had rooted. This cover caused uniform 161 germination of the test plants, unless this was adversely affected by the active compound. For the post-emergence treatment, the test plants were first 5 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 10 into the test containers a few days prior to treatment. The 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 0 C or 20 15 to 350C. 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 20 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 25 following species: Bayer code Common name ABUTH velvet leaf AMARE common amaranth 30 CHEAL lambsquarters (goosefoot) COMBE commelinal bengal GALAP harrit cleavers IPOSS morning glory POLPE redshank 35 PHBPU common morning glory SOLNI black nightshade VERSS speedwell TRZAW winter wheat 40 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 refer to the 45 numbers in Tables 7 and 8.
162 The herbicidal activities given below were determined after post-emergence application of the compounds in a greenhouse. Example compound Ib No.6 5 N O 00 10 VNN CI 15 Application rate 62.5 31.3 (g of a.s./ha) Test plants ABUTH 100 100 20 CHEAL 100 100 IPOSS 100 100 SOLNI 100 100 VERSS 100 100 25 Example compound Ib No.7 N O 30 N _CI
--
0 35 Application rate 15.6 7.8 (g of a.s./ha) Test plants 40 ABUTH 100 100 CHEAL 100 100 IPOSS 100 100 SOLNI 100 100 45 Example compound Ib No. 17 163 N O0 5 yN N S
CH
2 C-CH 10 Application rate 62.5 31.3 (g of a.s./ha) Test plants ABUTH 100 100 CHEAL 100 100 15 IPOSS 98 98 SOLNI 100 100 VERSS 100 80 Example compound Ib No. 37 20 -NyN 25
CH
3 Application rate 62.5 31.3(g of a.s./ha) 30 Test plants TRZAW 20 10 ABUTH 100 100 CHEAL 100 100 35 IPOSS 100 100 SOLNI 100 100 VERSS 100 100 Example compound Ib No. 81 40 45 164 0 N O F 5 CN N - CI 10 Application rate 62.5 31.3 (g of a.s./ha) 15 Test plants ABUTH 100 100 CHEAL 100 100 IPOSS 100 100 SOLNI 100 100 20 VERSS 100 100 Example compound Ib No. 78 25 I NN -CI 30
>CH
2
CH=CH
2 Application rate 62.5 31.3 (g of a.s./ha) 35 Test plants ABUTH 100 100 CHEAL 100 100 IPOSS 100 100 SOLNI 100 100 40 VERSS 100 100 Example compound Ia No. 76 45 Application rate 15.6 7.8 (g of a.s./ha) Test plants ABUTH 100 100 165 AMARE 100 100 CHEAL 100 100 COMBE 100 100 POLPE 100 100 5 Example compound Ia No. 4 Application rate 15.6 7.8 (g of a.s./ha) 10 Test plants ABUTH 100 100 AMARE 100 100 GALAP 98 98 POLPE 100 100 15 Example compound Ia, No. 92 Application rate 7.8 3.9 (g of a.s./ha) 20 Test plants ABUTH 100 98 AMARE 100 100 COMBE 100 90 POLPE 100 100 25 Example compound Ib No. 94 Application rate 15.6 7.8 (g of a.s./ha) 30 Test plants ABUTH 100 85 AMARE 100 100 POLPE 100 100 35 Example compound Ib No. 32 Application rate 31.3 15.6 (g of a.s./ha) Test plants 40 ABUTH 100 100 AMARE 100 100 PHBPU 100 100 POLPE 100 98 45 166 Compound from Example 6 N>, OCH 3 F 5 OvN N /
CH
2 C=CH 10 Application rate 15.6 7.8 (g of a.s./ha) Test plants ABUTH 100 100 15 AMARE 100 100 CHEAL 100 100 POLPE 100 100 20 25 30 35 40 45

Claims (7)

1. A substituted urea of the formula Ia or Ib 5 x x (RA)m NCNH-Q Z NC-NH- Q R (RA)m R 10 la Ib in which the variables X, Z, m, R and RA are as defined below: 15 X is S or 0; Z is 0, S, S=0 or SO 2 ; 20 m has the value 0, 1, 2 or 3; R is hydrogen, C(O)ORio, C(O)SR10, C(S)ORio, C(S)SR 1 o, CO 2 H, CHO, cyano, C(O)NR 1 1 R 1 2 , C(S)NR 1 lR 1 2 , C(O)NHC(O)Cl, C(O)NHS(O) 2 Cl, C(O)NHC(O)OR 1 2 ', C(O)NHS(0) 2 R 2 ', 25 C(O)NHS(0) 2 0R1 2 ', C(O)R 2 , P(O)Rl(ORI), P(O)(ORI) 2 , S(O)nR 2 where n = 0, 1 or 2, or SO 2 NHR 1 ; RA is hydroxyl, C0 2 RI, halogen, cyano, C(O)N(Rl) 2 , where the radicals R 1 are, if appropriate, different from one 30 another, is OR 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, COR 1 , S(O)nR 1 where n = 0, 1 or 2, or is C(O)SR1; and in which 35 Q is one of the radicals Qi to Q6: 3 3 3 40 R4 R4 R4 R5 Y N N;,, Y URG UR 6 45 Q-1 0-2 0-3 168 3 3 3 Y y R4 5 N Y' O TR7 0 0r O R 9 0-4 Q-5 Q-6 10 in which Y and Y' independently of one another are 0 or S; 15 T is a chemical bond or 0; U is a chemical bond, Ci-C 4 -alkylene, 0, S, SO or SO 2 ; and the radicals R 1 to R 3 0 are as defined below: 20 R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, Ci-C 3 -alkoxy-Ci-C 3 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; R 2 is Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, 25 C 3 -C 6 -alkynyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, hydroxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfinyl-Ci-C 6 -alkyl, 30 Ci-C 6 -alkylsulfonyl-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -cycloalkoxy-Ci-C 6 -alkyl, 35 C 3 -C 6 -alkenyloxy-Ci-C 6 -alkyl, C 3 -C 6 -alkynyloxy-Ci-C 6 -alkyl, Ci-C 6 -haloalkoxy-Ci-C 6 -alkyl, C 3 -C 6 -haloalkenyloxy-Ci-C 6 -alkyl, C 3 -C 6 -haloalkynyloxy-Ci-C 6 -alkyl, 40 C 3 -C 6 -cycloalkyl-Ci-C 6 -thioalkyl, C 3 -C 6 -alkenylthio-Ci-C 6 -alkyl, C 3 -C 6 -alkynylthio-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, C 3 -C 6 -halocyclo-Ci-C 6 -alkyl [sic], halo-C 2 -C 6 -alkenyl, Ci-C 6 -alkoxy-C 3 -C 6 -alkenyl, 45 Ci-C 6 -haloalkoxy-C 3 -C 6 -alkenyl, CI-C 6 -alkylthio-C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy-C 3 -C 6 -alkynyl, 169 Ci-C 6 -haloalkoxy-C 3 -C 6 -alkynyl, CI-C 6 -alkylthio-C 3 -C 6 -alkynyl, Ci-C 6 -alkylcarbonyl, CHR 1 COR 7 , CHR 1 P(O)(OR 7 ) 2 , P(O)(OR 7 ) 2 , CHR 1 P(S)(OR 7 ) 2 , CHRIC(O)NRilR1 2 , CHRIC(O)NH 2 , phenoxy-Ci-C 6 -alkyl or 5 benzyloxy-Ci-C 6 -alkyl, where the benzene rings of the two last-mentioned groups may for their part be substituted by halogen, C 1 -C 4 -alkyl or Ci-C 4 -haloalkyl; is benzyl which may be substituted by halogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl or is phenyl or pyridyl, each of which 10 may be substituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl or C 1 -C 4 -alkoxy; R 3 is hydrogen or halogen; 15 R 4 is Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, cyano or NO 2 ; R 5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, CI-C 6 -alkyl, C 2 -C 6 -alkenyl, C2-C 6 -alkynyl, 20 Ci-C 6 -haloalkyl, Cl-C 6 -haloalkoxy, Ci-C 6 -haloalkylthio, Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)carbonyl, Ci-C 6 -alkylthio-(Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkyl)iminooxycarbonyl, C 1 -C 6 -alkoxy-Ci-C 6 -alkyl, C 1 -C 6 -alkoxyamino-Ci-C 6 -alkyl, 25 Ci-C 6 -alkoxy-Ci-C 6 -alkylamino-Ci-C 6 -alkyl, is CI-C 6 -alkoxy, Ci-C 6 -alkylthio, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkylthio, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylthio, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynylthio, 30 (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -alkyl)carbonylthio, (Ci-C 6 -alkoxy)carbonyloxy, (C2-C 6 -alkenyl)carbonyloxy, (C 2 -C 6 -alkenyl)carbonylthio, (C 2 -C 6 -alkynyl)carbonyloxy, (C 2 -C 6 -alkynyl)carbonylthio, Ci-C6-alkylsulfonyloxy or Ci-C 6 -alkylsulfonyl, where each of the 17 last-mentioned 35 radicals may, if desired, carry one, two or three substituents selected from the group consisting of: - halogen, nitro, cyano, hydroxyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -alkenyloxy, 40 C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, Ci-C 6 -alkylsulfonyl, Ci-C6-alkylideneaminooxy, oxo, =N-OR 13 ; 45 - phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned groups may carry one, two or three substituents selected from the group consisting of 170 halogen, nitro, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; - -CO-R 1 4 , -CO-OR 1 4 , -CO-SR 1 4 , -CO-N(R 1 4 )-R 1 5 , -OCO-R 1 4 , 5 -OCO-OR 14 ', -OCO-SR 1 4 ', -OCO-N(R 1 4 )-R 1 5 , -N(R1 4 )-R 1 5 , and -C(R 1 6 )=N-OR 1 3 ; is C(Zl)-R 1 7 , -C(=NR1 8 )R 1 7 , C(R1 7 )(Z 2 R1 9 )(Z 3 R 2 0), C(R 1 7 )=C(R 2 1 )-CN, C(R 1 7 )=C(R 2 1 )-CO-R 2 2 , 10 -CH(R 1 7 )-CH(R 2 1 )-COR 2 2 , -C(R17)=C(R 2 1 )-CH 2 -CO-R 2 2 , -C(R1 7 )=C(R 2 1)-C(R 2 3 )=C(R 2 4 )-CO-R 2 2, -C(R1 7 )=C(R 2 1 )-CH 2 -CH(R 2 5 )-CO-R 2 2 , -CO-OR 2 6 , -CO-SR 2 6 , -CON(R 2 6 )-OR 1 3 , -C=C-CO-NHOR 13 , -C=C-CO-N(R 2 6 )-OR 1 3 , -C-C-CS-NH-OR 1 3 , -C=C-CS-N(R 2 6 )-OR 1 3 , 15 -C(R 1 7 )=C(R 2 1 )-CO-NHOR1 3 , -C(R 1 7 )=C(R 2 1 )-CO-N(R 2 6 )-OR 1 3 , -C(R1 7 )=C(R 2 1 )-CS-NHOR 1 3 , -C(R 1 7 )=C(R 2 1 )-CS-N(R 2 6 )-OR 1 3 , -C(R17)=C(R 2 1 )-C(R 1 6 )=N-OR1 3 , C(R 1 6 )=N-OR 1 3 , -C=C-C(R 1 6 )=NOR1 3 , C(Z 2 R 1 9 )(Z 3 R 2 0 )-OR 2 6 , -C(Z 2 R 1 9 )(Z 2 R 2 0 )SR 2 6 , C(Z 2 R 19 )(Z 3 R 2 0 )-N(R 2 7 )R 2 8 , -N(R 2 7 )-R 2 8 , 20 -CO-N(R 2 7 )-R 2 8 or -C(R1 7 )=C(R 2 1 )CO-N(R 2 7)R 2 8 ; where Z 1 , Z 2 , Z 3 independently of one another are oxygen or sulfur; R 6 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, CI-C 3 -alkoxy-Ci-C 3 -alkyl, C 3 -C 6 -alkenyl, 25 Ci-C 3 -alkoxy-C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, Ci-C 3 -alkoxy-C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 3 -C 7 -cycloalkyl, 3- to 7-membered saturated heterocyclyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl 30 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-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -cyanoalkyl, Ci-C 4 -hydroxyalkyl, 35 Ci-C 4 -aminoalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, CI-C 4 -alkylsulfonyl, Ci-C 4 -haloalkylsulfonyl, (Ci-C 4 -alkoxy)carbonyl, (Ci-C 4 -alkyl)carbonyl, (Ci-C 4 -haloalkyl)carbonyl, (Ci-C 4 -alkyl)carbonyloxy, 40 (Ci-C 4 -haloalkyl)carbonyloxy, di(Ci-C 4 -alkyl)amino, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 4 -alkenyloxy, C 3 -C 4 -alkenylthio, C 3 -C 4 -alkynyloxy and C 3 -C 4 -alkynylthio; R 7 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, 45 Ci-C 3 -alkoxy-Ci-C 3 -alkyl, C 2 -C 6 -cyanoalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl; 171 R 8 is hydrogen, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl or halogen; R 9 is hydrogen, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl; or 5 R 8 and R 9 together are C=0; R 10 is Ci-C 1 5 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 1 0 -alkenyl, C 3 -C 1 0 -alkynyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, 10 Ci-C 6 -alkylsulfinyl-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl-Ci-C 6 -alkyl, Ci-C 3 -alkoxy-Ci-C 3 -alkoxy-C1-C 3 -alkyl, C3-C 6 -cycloalkyl-Ci-C 6 -alkyl, carboxyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, 15 Ci-C6-alkoxycarbonyl-C2-C 6 -alkenyl, C 3 -C 6 -alkenyloxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-Ci-C 6 -alkyl, C 3 -C 8 -cycloalkoxy-Ci-C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkyl, 20 C 3 -C 6 -alkynyloxy-C 1 -C 6 -alkyl, Ci-C 6 -haloalkoxy-Ci-C 6 -alkyl, C 3 -C 6 -haloalkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -haloalkynyloxy-Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl-Ci-C 6 -thioalkyl, 25 C 3 -C 6 -alkenylthio-C 1 -C 6 -alkyl, C 3 -C 6 -alkynylthio-C 1 -C 6 -alkyl, cyano-Ci-C 6 -alkyl, C 3 -C 6 -halocyclo-Ci-C 6 -alkyl, halo-C 3 -C 6 -alkenyl, CI-C 6 -alkoxy-C 3 -C 6 -alkenyl, Ci-C 6 -haloalkoxy-C 3 -C 6 -alkenyl, 30 C 1 -C 6 -alkylthio-C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy-C 3 -C 6 -alkynyl, . C 1 -C 6 -haloalkoxy-C 3 -C 6 -alkynyl, CI-C 6 -alkylthio-C 3 -C 6 -alkynyl, CHRICOR 7 , CHRIP(O)(OR 7 ) 2 , P(O)(OR 7 ) 2 , CHRlP(S)(OR 7 ) 2 , CHR 1 C(O)NR 1 lR 1 2 , CHR 1 C(O)NH 2 , 35 Ci-C 6 -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, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl; 40 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, 45 difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may in each case be mono- to pentasubstituted by halogen, 172 Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, CI-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, amino, Ci-C 4 -monoalkylamino, C 1 -C 4 -dialkylamino, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxycarbonyl, 5 Ci-C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, hydroxyl, nitro or cyano; R 11 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy; 10 R 12 is hydrogen, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-C 2 -C 6 -alkenyl, where the alkenyl 15 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 20 may be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, CI-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, amino, Ci-C 4 -monoalkylamino, Ci-C 4 -dialkylamino, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxycarbonyl, 25 Ci-C 4 -alkoxycarbonyl-Ci-C 4 -alkyl, hydroxyl, nitro or cyano or R 11 and R 12 together with the common nitrogen atom are a 30 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-(Ci-C 6 -alkyl)-; 35 R1 2 ' is as defined for R 12 , but excluding hydrogen; R 13 is hydrogen, Ci-C 6 -alkyl, CI-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, hydroxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, 40 Ci-C 6 -alkylthio-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-C 2 -C 6 -alkenyl, (Ci-C 6 -alkyl)carbonyloxy-Ci-C 6 -alkyl or 45 phenyl-Ci-C 6 -alkyl, in which the phenyl ring may, if desired, carry one, two or three substituents selected from the group consisting of cyano, nitro, halogen, 173 Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; R 14 is hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, 5 C 3 -C 6 -alkynyl, CI-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, (C 3 -C 6 -alkenyloxy)carbonyl-Ci-C 6 -alkyl, phenyl or phenyl-Ci-C 6 -alkyl, where the phenyl ring of the two last-mentioned groups may be unsubstituted or may carry 10 one, two or three radicals selected from the group consisting of halogen, nitro, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkyl)carbonyl; R 14 ' is as defined for R 14 , but excluding hydrogen; 15 R 15 is hydrogen, hydroxyl, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkoxy, C 3 -C 6 -alkenyl or C 3 -C 6 -alkenyloxy; 20 R 16 is hydrogen, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, Ci-C 6 -alkylthio, Ci-C 6 -haloalkylthio, (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -haloalkyl)carbonyloxy, Ci-C 6 -alkylsulfonyloxy or Ci-C 6 -haloalkylsulfonyloxy, 25 where the 12 last-mentioned radicals may carry one of the following substituents: hydroxyl, cyano, hydroxycarbonyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkyl)aminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, (Ci-C 6 -alkyl)carbonyloxy, 30 C 1 -C 6 -alkoxy-(Ci-C 6 -alkyl)aminocarbonyl; is (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -haloalkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkoxy)carbonyloxy, (Ci-C 6 -alkyl)carbonylthio, (Ci-C 6 -haloalkyl)carbonylthio, 35 (Ci-C 6 -alkoxy)carbonylthio, C 2 -C 6 -alkenyl, (C 2 -C 6 -alkenyl)carbonyloxy, C 2 -C 6 -alkenylthio, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 3 -C 6 -alkynylthio, (C 2 -C 6 -alkynyl)carbonyloxy, C3-C6-alkynylsulfonyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, 40 C 3 -C 6 -cycloalkylthio, (C 3 -C 6 -cycloalkyl)carbonyloxy, C 3 -C 6 -cycloalkylsulfonyloxy; is phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-Ci-C 6 -alkyl, 45 phenyl-Ci-C 6 -alkoxy, phenyl-Ci-C 6 -alkylthio, phenyl-(Ci-C 6 -alkyl)carbonyloxy or phenyl-(Ci-C 6 -alkyl)sulfonyloxy, where the phenyl rings 174 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, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy 5 and (Ci-C 6 -alkoxy)carbonyl; R 17 is hydrogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C6-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy-Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl; 10 R 18 is hydrogen, hydroxyl, Ci-C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkoxy, 15 C 5 -C 7 -cycloalkenyloxy, Ci-C 6 -haloalkoxy, C 3 -C 6 -haloalkenyloxy, hydroxy-Ci-C 6 -alkoxy, cyano-Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl-Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, C 1 -C 6 -alkoxy-C 3 -C 6 -alkenyloxy, (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -haloalkyl)carbonyloxy, 20 (Ci-C 6 -alkyl)carbamoyloxy, (Ci-C 6 -haloalkyl)carbamoyloxy, (Ci-C 6 -alkyl)carbonyl-Ci-C6 -alkyl, (Ci-C 6 -alkyl)carbonyl-Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C6 -alkoxy, 25 Ci-C 6 -alkylthio-Ci-C 6 -alkoxy, di(Ci-C 6 -alkyl)amino-Ci-C 6 -alkoxy, -N(R 29 )R 30 , phenyl which for its part may carry one, two or three substituents, in each case selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, 30 Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; is phenyl-Ci-C 6 -alkoxy, phenyl-(Ci-C 6 -alkyl), phenyl-C 3 -C 6 -alkenyloxy or phenyl-C 3 -C 6 -alkynyloxy, where 35 in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -0-, -S- or -N(Ci-C 6 -alkyl)- and where the phenyl rings in the four last-mentioned groups may be unsubstituted or may for their part carry one to three 40 substituents, selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; is C 3 -C 7 -heterocyclyl, C 3 -C 7 -heterocyclyl-Ci-C 6 -alkyl, 45 C 3 -C 7 -heterocyclyl-Ci-C 6 -alkoxy, C 3 -C 7 -heterocyclyl-C 3 -C 6 -alkenyloxy or C 3 -C 7 -heterocyclyl-C 3 -C 6 -alkynyloxy, where in -each case 175 one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -0-, -S- or -N(Ci-C 6 -alkyl)- and where each heterocycle may be saturated, unsaturated or aromatic and is either 5 unsubstituted or for its part carries one to three substituents, selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; 10 R 1 9 , R 20 independently of one another are Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, CI-C 6 -alkoxy-Ci-C 6 -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 15 not adjacent to the variables Z 2 and Z 3 may be replaced by -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)- and where the carbon chain may carry one to three substituents selected from the group consisting of cyano, nitro, amino, halogen, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, Ci-C 6 -alkoxy, 20 C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, Ci-C 6 -haloalkyl, cyano-Ci-C 6 -alkyl, hydroxy-Ci-C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-CI-C 6 -alkyl, C 3 -C 6 -alkynyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, carboxyl, (Ci-C 6 -alkoxy)carbonyl, 25 (Ci-C 6 -alkyl)carbonyloxy-C 1 -C 6 -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 30 ring members, one or two heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen and Ci-C 6 -alkyl-substituted nitrogen and which may for its part, if desired, carry one or two of the following substituents: cyano, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, 35 Ci-C 6 -alkoxy, cyano-Ci-C 6 -alkyl, CI-C 6 -haloalkyl and (Ci-C 6 -alkoxy)carbonyl; R 21 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkyl)carbonyl or 40 (Ci-C 6 -alkoxy)carbonyl; R 22 is hydrogen, O-R 3 1 , S-R 31 , Ci-C 6 -alkyl which may carry one or two Ci-C 6 -alkoxy substituents, is C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, 45 Ci-C 6 -alkylthio-Ci-C 6 -alkyl, Ci-C 6 -alkyliminooxy, -N(R27)R28 or phenyl which may be unsubstituted or may carry one to three -substituents, in each case selected 176 from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; 5 R 23 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, -N(R 27 )R 2 8 or phenyl which for its part may carry one to three substituents selected from the group consisting of cyano, 10 nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; R 24 is hydrogen, cyano, halogen, CI-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkyl, (Ci-C 6 -alkyl)carbonyl or 15 (C 1 -C 6 -alkoxy)carbonyl; R 25 is hydrogen, cyano, Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl; R 26 , R 31 independently of one another are hydrogen, 20 Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, (Ci-C 6 -alkyl)carbonyl, 25 (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkyl)carbonyloxy, (C 3 -C 6 -alkenyloxy)carbonyl; are (Ci-C 6 -haloalkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, Ci-C 6 -alkylaminocarbonyl, di(Ci-C 6 -alkyl)aminocarbonyl, 30 Ci-C 6 -alkyloximino-Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl; are phenyl or phenyl-Ci-C 6 -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 35 consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; R 2 7 , R 2 8 , R 2 9 , R 3 0 independently of one another are hydrogen, CI-C 6 -alkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, 40 C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, C 1 -C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C6 -alkyl, 45 are (Ci-C 6 -alkoxy)carbonyl-C 2 -C 6 -alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are Ci-C 6 -alkylsulfonyl, 177 (Ci-C6-alkoxy)carbonyl-Cl-C 6 -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 5 selected from the group consisting of cyano, nitro, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; or R 27 and R 2 8 and/or 10 R 2 9 and R 3 0 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: 15 -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)-; 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 01 in which R 3 = fluorine and 20 R4 = chlorine, and R 5 is selected from the group consisting of isopropoxy, propargyloxy, allyloxy, benzyloxy and isopropoxycarbonyl, hydroxyiminomethyl, methoxyiminomethyl, CH=NOCH 2 CO 2 CH 3 , -CH=N-0-C(CH 3 ) 2 -CO 2 CH 3 , propargyloxyiminomethyl, 25 -CH=C(Cl)-CO 2 CH 3 , -CH=C(Cl)C0 2 C 2 H 5 , -CH=C(Cl)-C0 2 -CH 2 -CO 2 CH 3 , -CH=C(Cl)-C0 2 -CH(CH 3 )CO 2 CH 3 , -CH=C(Cl)-C0 2 -CH 2 -CO 2 -tert-butyl, -CH=C(Cl)-CO 2 H, -CH=C(Cl)-CONHOCH 3 , -CH=C(Cl)-CONHOC 2 H 5 or -CH=N-0-CH (CH 3 ) -CO 2 CH 3 ; 30 or Q is a radical of the formula Q1 where R 3 R 5 [sic] = hydrogen and R 5 = chlorine, or Q is a radical of the formula Q1 where R 3 = R4= chlorine and R 5 = H, methoxyiminomethyl, -CH=C(Cl)CO 2 H or -CH=C(Cl)-CO 2 C(CH 3 ) 3 ; 35 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 7 = propargyl, allyl or
3-(ethoxycarbonyl)prop-2-yl or Q is a radical of the 40 formula Q1 where R 3 = R4 = chlorine and R 5 = hydrogen; and the agriculturally useful salts of the compounds of the formulae Ia and Ib. 45 2. A compound of the formula Ia or Ib as claimed in claim 1 where the variables are as defined below: 178 Z is O or S RA is C0 2 RI, halogen, cyano, OR 2 or Ci-C 3 -alkyl; 5 m is 0, 1, 2 or 3; Q is Qi, Q2 or Q4; X, Y and Y' independently of one another are 0 or S; 10 T is a chemical bond or 0; U is a chemical bond, Ci-C 4 -alkylene, 0 or S; 15 R is hydrogen, C(O)OR10, C(O)SR 1 0, C(S)OR 10 , C(S)SR 1 o, CHO, CN, C(O)R 2 , C(O)NRi 1 R 1 2 , C(S)NR 11 R 1 2 , C(O)NHC(O)OR 12 ', C(O)NHS(0) 2 Ri 2 ', C(O)NHS(O) 2 OR 1 2 '; R 1 is hydrogen or Ci-C 3 -alkyl; 20 R 2 is Ci-C 3 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, Ci-C 3 -haloalkyl, Ci-C 3 -alkoxycarbonyl-Ci-C 3 -alkyl, cyano-Ci-C 3 -alkyl, benzyl, which may be substituted by halogen, Ci-C 4 -alkyl 25 or trifluoromethyl, or is phenyl, which may be substituted by halogen, CI-C 4 -alkyl, trifluoromethyl or CI-C 4 -alkoxy; 30 R 3 is hydrogen, fluorine or chlorine; R 4 is chlorine, trifluoromethyl or cyano; R 5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, 35 Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -haloalkoxy, Ci-C 6 -haloalkylthio, Ci-C 6 -alkoxy-(Ci-C 6 -alkyl)carbonyl, Ci-C 6 -alkylthio-(Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkyl)iminooxycarbonyl, Cl-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxyamino-Ci-C 6 -alkyl, 40 Cl-C 6 -alkoxy-Ci-C 6 -alkylamino-Ci-C 6 -alkyl, is Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkylthio, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylthio, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynylthio, 45 (Ci-C 6 -alkyl)carbonyloxy, (Ci-C 6 -alkyl)carbonylthio, (Ci-C 6 -alkoxy)carbonyloxy, (C 2 -C 6 -alkenyl)carbonyloxy, (C 2 -C 6 -alkenyl)carbonylthio, (C 2 -C 6 -alkynyl)carbonyloxy, 179 (C2-C 6 -alkynyl)carbonylthio, C1-C 6 -alkylsulfonyloxy or Ci-C 6 -alkylsulfonyl, where each of these 17 radicals may, if desired, carry one, two or three substituents, selected from the group consisting of: 5 - halogen, nitro, cyano, hydroxyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, Ci-C 6 -alkoxy-Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkylsulfinyl, 10 Ci-C 6 -alkylsulfonyl, Cl-C6-alkylideneaminooxy, oxo, =N-OR 1 3 - phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned substituents may for their part carry 15 one, two or three substituents, in each case selected from the group consisting of halogen, nitro, cyano, Ci-C 6 -alkyl, C 1 -C 6 -haloalkyl, Ci-C 6 -alkoxy and (Ci-C 6 -alkoxy)carbonyl; 20 - -CO-R 1 4 , -CO-OR 1 4 , -CO-SR 1 4 , -CO-N(R 14 )-Rl 5 , -OCO-R 1 4 , -OCO-OR 1 4 ', -OCO-SR 1 4 ', -OCO-N(R 1 4 )-R 1 5 , -N(R 1 4 )-R 1 5 , and -C(R 1 6 )=N-OR 1 3 ; is C(Zl)-R 1 7 , -C(=NR1 8 )R 1 7 , C(R 1 7 )(Z 2 R 1 9 )(Z 3 R 2 0 ), 25 C(R 1 7 )=C(R 2 1 )-CN, C(R 1 7 )=C(R 2 1 )-CO-R 2 2 , -CH(R 1 7 )-CH(R 2 1 )-COR 2 2 , -C(R 1 7 )=C(R 2 1 )-CH 2 -CO-R 2 2 , -C (R 17 ) =C (R 2 1 ) -C (R 2 3 ) =C (R 2 4 ) -CO-R 2 2 , -C(R 1 7 )=C(R 2 1 )-CH 2 -CH(R 2 5 )-CO-R 2 2 , -CO-OR 2 6 , -CO-SR 2 6 , -CON(R 2 6 )-OR 1 3 , -C=C-CO-NHOR 1 3 , -C=C-CO-N(R 2 6 )-OR 1 3 , 30 -C=C-CS-NH-OR 1 3 , -C=C-CS-N(R 2 6 )-OR 1 3 , -C(R 1 7 )=C(R 2 1 )-CO-NHOR1 3 , -C(R 1 7 )=C(R 2 1 )-CO-N(R 2 6 )-OR1 3 , -C(R 1 7 )=C(R 2 1 )-CS-NHOR1 3 , -C(R 1 7 )=C(R 2 1 )-CS-N(R 2 6 )-OR1 3 , -C(R 1 7 )=C(R 2 1 )-C(R 1 6 )=N-OR 1 3 , C(R 1 6 )=N-OR 1 3 , -C=C-C(R 1 6 )=NOR1 3 , C(Z 2 R 1 9 )(Z 3 R 2 0 )-OR 2 6 , 35 -C(Z 2 R1 9 )(Z 2 R 2 0)SR 2 6 , C(Z 2 R 1 9 )(Z 3 R 2 0 )-N(R 2 7 )R 2 8 , -N(R 2 7 )-R 2 8 , -CO-N(R 2 7 )-R 2 8 or -C(R1 7 )=C(R 2 1 )CO-N(R 2 7 )R 2 8 ; in which Z 1 , Z 2 , Z 3 independently of one another are oxygen or sulfur; R 6 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, 40 C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, or is 3- to 7-membered saturated heterocyclyl which contains one or more oxygen and/or sulfur atoms; R 7 is hydrogen or Ci-C 6 -alkyl; 45 R 8 is hydrogen or Ci-C 3 -alkyl; 180 R 9 is hydrogen, Ci-C 3 -alkyl R 8 and R 9 together are C=O; 5 R 10 is Ci-C 15 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 1 0 -alkenyl, C 3 -C 1 0 -alkynyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -alkenyloxy-Ci-C 6 -alkyl, C 3 -C 6 -alkynyloxy-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, 10 is phenyl or benzyl which may in each case be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, amino, C 2 -C 4 -monoalkylamino, Ci-C 4 -dialkylamino, 15 CI-C 4 -alkoxycarbonyl, nitro or cyano; R 11 is hydrogen, Ci-C 6 -alkyl or Ci-C 6 -alkoxy; R 12 is hydrogen, CI-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, 20 Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, phenyl or benzyl which may be mono- to pentasubstituted by halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -dialkylamino, Ci-C4-alkoxycarbonyl, nitro or cyano; or 25 R 12 ' is as defined for R 1 2 , but excluding hydrogen; R 11 and R 1 2 together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle; 30 R 13 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, cyano-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl or phenylalkyl, where 35 the phenyl ring may be mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl or Ci-C 3 -alkoxy; R 14 is hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, 40 C 3 -C 6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)carbonyl-Ci-C 6 -alkyl, C3-C 6 -alkenyloxycarbonyl-Cl-C 6 -alkyl, 45 181 is phenyl or benzyl which may be unsubstituted on the phenyl ring or may be mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl or Ci-C 3 -alkoxy; 5 R 14 ' is as defined for R 1 4 , but excluding hydrogen; R 15 is hydrogen, hydroxyl, CI-C 6 -alkyl, Ci-C 6 -alkoxy, (Ci-C 3 -alkoxy)carbonyl-C 1 -C 3 -alkoxy, C 3 -C 6 -alkenyl or 10 C 3 -C 6 -alkynyl; R 16 is hydrogen, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, (Ci-C 6 -alkoxy)carbonylalkoxy, C 2 -C 6 -alkenyl, 15 (C 2 -C 6 -alkenyl)carbonyloxy, C 3 -C 6 -alkynyl, (C 2 -C 6 -alkynyl)carbonyloxy, is phenyl, phenoxy or benzyl, where the phenyl rings of the 3 last-mentioned radicals may be unsubstituted or 20 mono- to trisubstituted by halogen, cyano, nitro, Ci-C 3 -alkyl, Ci-C 3 -haloalkyl, Ci-C 3 -alkoxy or (Ci-C 3 -alkoxy)carbonyl; R 17 is hydrogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, 25 C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl or (Ci-C 6 -alkoxy)carbonyl; R 18 is hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -haloalkyl, 30 C 1 -C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkoxy, (Ci-C 6 -alkoxy)carbonyl-Ci-C6 -alkyl, is phenyl or phenyl-(Ci-C 6 -alkyl), where the two last-mentioned phenyl radicals may be substituted by 35 halogen, cyano, nitro, CI-C 3 -alkyl, Ci-C 3 -haloalkyl, CI-C 3 -alkoxy or (Ci-C 3 -alkoxy)carbonyl; R 19 , R 2 0 independently of one another are Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, 40 C 1 -C 6 -alkoxy-Ci-C 6 -alkyl, or R 19 and R 2 0 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 45 Z 2 and Z 3 may be replaced by -0-, -S-, -N=, -NH- or -N(Ci-C 6 -alkyl)- and where the carbon chain may be 182 substituted once to three times by halogen or Ci-C 6 -alkyl; R 21 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl 5 or CI-C 6 -alkoxy; R 22 is hydrogen, OR 3 1 , S-R 3 1 , Ci-C 6 -alkyl, which may carry one or two CI-C 6 -alkoxy substituents, is C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -haloalkyl or C 3 -C 6 -cycloalkyl; 10 R 23 is hydrogen, cyano, halogen, CI-C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; R 24 is hydrogen, cyano, halogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy or 15 Ci-C 6 -haloalkyl; R 25 is hydrogen, cyano or Ci-C 6 -alkyl; R 26 , R 31 independently of one another are hydrogen, 20 CI-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: cyano, halogen, CI-C 6 -alkoxy, Ci-C 6 -alkylcarbonyl, (C 1 -C 6 -alkoxy)carbonyl; 25 or are (Ci-C 6 -alkyl)carbonyl, (Ci-C 6 -alkoxy)carbonyl, phenyl or phenyl-Ci-C 6 -alkyl; R 27 , R 2 8 , R 2 9 , R 3 0 independently of one another are hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, 30 C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, C 1 -C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylcarbonyl, (Ci-C 6 -alkoxy)carbonyl, or R 27 and R 2 8 and/or R 29 and R 3 0 together with the respective 35 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. 40 3. A compound of the formula Ia or Ib as claimed in claim 1 or 2 in which Q is Q 1 and R 5 is Ci-C 6 -alkoxy, C 2 -C 6 -alkenyloxy or C 2 -C 6 -alkynyloxy, where each of the 3 last-mentioned radicals may, if 45 desired, carry one to three substituents, in each case selected from the group consisting of halogen, Ci-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, 183 Ci-C 6 -alkylsulfonyl, -CO-R 14 , -CO-OR 14 , -CO-N(R 1 4 )-R 1 5 , -N(R1 4 )-R1 5 and -C(R 1 6 )=N-OR 13 ; is -CO-R 17 , -C(NR 18 )-R 1 7 , -C(R 1 7 )(OR 19 )(OR 20 ), 5 -C(R 1 7 )=C(R 2 1 )-CO-R 22 , -CH(R 17 )-CH(R 2 1 )-CO-R 22 , -CO-OR 2 6 , -CO-N(R 2 6 )-OR 13 , -C(R1 7 )=C(R 21 )-CO-N(R 26 )-OR 13 , -C(R 1 6 )=N-OR 13 , -C(OR 19 )(OR 2 0 )-OR 2 6 , -N(R 27 )R 28 , -CON(R 27 )R 28 or -C(R 1 7 )=C(R 27 )CO-N(R 27 )R 28 ; 10 in which R 13 to R 22 and R 2 6 to R 2 8 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 different from hydrogen if Q is Q1, Q4, Q5 or Q6 and Z is oxygen. 15 5. A compound of the formula Ia or Ib as claimed in any of the preceding claims in which R is CI-C 6 -alkyloxycarbonyl, (Ci-C 6 -alkoxy)thiocarbonyl, 20 (Ci-C 6 -alkylthio)carbonyl, -CHO, -CN, -C(O)NRilR1 2 , -C(O)NHC(O)Cl, -C(O)NHS(0) 2 Cl, C(O)NHC(O)OR 12 ', C(O)NHS(O) 2 R1 2 ', C(O)R 2 , P(O)Rl(ORI), P(O)(ORI) 2 ; S(O)R 2 , S(O) 2 R 2 or S(O) 2 NHR 2 25 in which the variables R 1 , R 2 , R 11 , R 12 and R 12 ' are as defined below: R 1 is Ci-C 6 -alkyl 30 R 2 is C 1 -C 6 -alkyl R 11 is hydrogen or Ci-C 6 -alkyl R 12 is hydrogen, CI-C 6 -alkyl or Ci-C 6 -alkoxy, and 35 R 12 ' is Ci-C 6 -alkyl or Ci-C 6 -alkyloxy; Z is O or S, 40 X is 0 or S, and m has the value 0. 6. A compound as claimed in claim 5 in which Q is Q1, 45 R 3 is hydrogen or halogen 184 R 4 is hydrogen, halogen or cyano, and 5 R 5 is Cl-C 6 -alkyl, C 3 -C 6 -alkenyl, Cl-C 6 -haloalkyl, C 3 -C 6 -haloalkenyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C 1 -C 6 -alkylthio, Cl-C 6 -haloalkylthio, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, haloalkenyloxy, alkenylthio, haloalkenylthio, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkoxy, 10 C3-C6-alkenyloxycarbonyl-Cl-C 6 -alkoxy, C 3 -C 6 -alkynyloxycarbonyl-C 1 -C 6 -alkoxy, Cl-C6-alkoxy-Cl-C 6 -alkoxycarbonyl-Cl-C 6 -alkoxy, (C 3 -C 6 -alkenyloxy) carbonyl-Cl-C 6 -alkoxycarbonyl-Cl-C 4 alkoxy, Cl-C 6 -alkoxycarbonyl-Cl-C 6 -alkylthio, 15 Cl-C6-alkenyloxycarbonyl-Cl-C 6 -alkylthio, Ci-C 6 -alkynyloxycarbonyl-Cl-C 6 -alkylthio, Cl-C6-alkoxy-Cl-C 6 -alkoxycarbonyl-Cl-C 6 -alkylthio, Cl-C 6 -alkoxyamino-Cl-C 6 -alkyl, N-C 1 -C 6 -alkoxy-N- (Cl-C 6 -alkyl )amino-Cl-C 6 -alkyl, 20 C-C 6 -alkylsulfonylamino, -C00R 26 , -C0NR 2 7 R 28 ,' -C(=NR1 8 )Rl 7 , -C(Rl 6 )=NORl1 3 , C(R 1 7 )=C(R 2 I)-CO-R 2 2 , where the variables R 13 , R 16 , R 17 , R 2 1 , R 22 , R 26 to R 28 are as defined below: 25 R 13 is Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, C 3 -0 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -cyanoalkyl or Cl-C6-alkoxycarbonyl-Cl-C 6 -alkyl; 30 R 16 is hydrogen, Cl-C 6 -alkyl, C 1 -C 6 -alkoxy, Cl-C 6 -alkoxycarbonyl-Cl-C 6 -alkyl, Cl-C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy or phenoxycarbonyl-C 1 -C 6 -alkoxy; 35 R 17 is hydrogen, Cl-C 6 -alkyl; R 21 is hydrogen, halogen, CI-C 6 -alkyl; R 22 is hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, 40 Cl-C 6 -alkoxycarbonyl-Cl-C 6 -alkyl; R 26 is Cl-C 6 -alkyl, C 3 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, Cl-C6-alkoxycarbonyl-Cl-C 6 -alkyl, C3-C6-alkenyloxycarbonyl-Cl-C 6 -alkyl, 45 C3-C6-alkynyloxycarbonyl-Cl-C 6 -alkyl, Cl-C 6 -alkoxyalkyl; 185 R 2 7 is hydrogen, CI-C 6 -alkyl; R 28 is hydrogen, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, 5 or R 2 7 and R 2 8 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring. 7. A compound of the formula Ia or Ib as claimed in claim 5 in 10 which Q is Q2 or Q3, where R 3 is hydrogen or halogen, 15 R 4 is hydrogen or halogen, Y is O or S, 20 U is a single bond, oxygen or Ci-C 4 -alkylene, and R 6 is hydrogen, halogen, cyano, Ci-C 6 -alkyl, CI-C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, saturated C 3 -C 7 -heterocyclyl which has one or two heteroatoms selected from the group consisting 25 of oxygen and sulfur in the ring, is Ci-C 6 -alkoxyalkyl, cyano-Ci-C 6 -alkyl, CO 2 H, Ci-C 6 -alkoxycarbonyl, Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl. 30 8. A compound of the formula Ia or Ib as claimed in claim 5 in which Q is Q4 or Q5, in which 35 R 3 is hydrogen or halogen Y is O or S Y' in the formula Q5 is oxygen or sulfur 40 T is a single bond, oxygen or Ci-C 4 -alkylene and R 7 is hydrogen, halogen, cyano, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, saturated C 3 -C7-heterocyclyl which has 45 one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, is Ci-C 6 -alkoxyalkyl, cyano-Ci-C 6 -alkyl, CO 2 H, Ci-C 6 -alkoxycarbonyl, 186 Ci-C 6 -alkoxycarbonyl-Ci-C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl.
9. A compound of the formula Ia or Ib as claimed in claim 5 in 5 which Q is Q6 R 3 is hydrogen or halogen 10 R 4 is hydrogen or halogen R 8 and R 9 independently of one another are hydrogen, Ci-C 6 -alkyl, halogen, cycloalkyl or Ci-C 6 -haloalkyl, or 15 RO and R 9 together with the carbon atom to which they are attached are a carbonyl group.
10. A compound of the formula Ia or Ib as claimed in any of the 20 preceding claims in which Q is Q1, Z is oxygen, 25 X is oxygen or sulfur, m has the value 0, 30 R is hydrogen, Ci-C 4 -alkoxycarbonyl or (Ci-C 4 -alkoxycarbonyl)iminocarbonyl, R 3 is fluorine, chlorine or hydrogen, 35 R 4 is halogen, and R 5 is CN, COOH, Ci-C 4 -alkoxyiminomethyl, Ci-C 4 -alkoxy, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -alkenyloxy, C3-C 6 -alkynyloxy, C 3 -C 6 -alkenyloxyiminomethyl, 40 (CI-C 4 -alkoxycarbonyl)-C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxyiminomethyl, 2-[CI-C 4 -alkoxycarbonyl]-2-chloroethyl, 2-[Ci-C 4 -alkoxycarbonyl]-2-chloroethenyl, Ci-C 4 -alkoxycarbonyl, (Ci-C 6 -alkoxycarbonyl)-Ci-C 4 -alkoxy, 45 (Ci-C 6 -alkoxycarbonyl)-Ci-C 4 -thioalkyl, 187 is COOR 2 6 where R 2 6 = Ci-C 4 -alkoxy-Ci-C 4 -alkyl or C 3 -C6-alkenyloxycarbonyl-Ci-C4-alkyl, is CONR 2 7 R 2 8 where R 2 7 = hydrogen or Ci-C 4 -alkyl and R 2 8 = 5 hydrogen, Ci-C 4 -alkyl or Ci-C 4 -alkoxy, is C(=NR 1 7 )Ri 8 in which R 1 7 is Ci-C 4 -alkoxy and R 18 is Ci-C 4 -alkoxy or Ci-C 4 -alkoxycarbonyl-Ci-C4-alkoxy. 10 11. 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 10 or an agriculturally useful salt of Ia or Ib and customary auxiliaries. 15 12. 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 10 or an agriculturally useful salt of Ia or Ib to act on plants, 20 their habitat and/or on seed.
13. The use of substituted ureas of the formula Ia or Ib in which the variables are as defined in any of claims 1 to 10 or their agriculturally useful salts as herbicides. 25 30 35 40 45
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