[go: up one dir, main page]

CA2355125A1 - Thiochromanoylcyclohexenone derivatives - Google Patents

Thiochromanoylcyclohexenone derivatives Download PDF

Info

Publication number
CA2355125A1
CA2355125A1 CA002355125A CA2355125A CA2355125A1 CA 2355125 A1 CA2355125 A1 CA 2355125A1 CA 002355125 A CA002355125 A CA 002355125A CA 2355125 A CA2355125 A CA 2355125A CA 2355125 A1 CA2355125 A1 CA 2355125A1
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
formula
cyano
phenyl
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
CA002355125A
Other languages
French (fr)
Inventor
Klaus Langemann
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Guido Mayer
Ulf Misslitz
Ulf Neidlein
Matthias Witschel
Norbert Gotz
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2355125A1 publication Critical patent/CA2355125A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

The invention relates to thiochromanoyl cyclohexenone derivatives of formula (I), wherein the variables have the following meanings: A is an optionally substituted, saturated or unsaturated alkyl chain; R1 is cyano, rhodano, nitro, OR4, SR5, SOR6, SO2R6, ONR6NR7, ON=CR6R8, NR9R10, P(O)R11R12, P(S)R11R12, CO2R6, optionally substituted phenyl or heterocyclyl; R2 is alky l, alkyl halide, alkoxy or halogenalkoxy; R3 is hydrogen, alkyl or halogen; X i s oxygen, sulphur, S=O, S(=O)2, CR13R14, C=O or C=NR15; m is 0, 1 or 2; n is 0 , 1, 2, 3 or 4; R16 is substituted (3-oxo-1-cyclohexen-2-yl)-carbonyl or substituted (1,3-dioxo-2-cyclohexyl)-methylidene; and to their agriculturall y useful salts. The invention relates to intermediate products and methods for producing thiochromanoyl cyclohexenone derivatives, to products containing them and the use of these derivatives or products containing them for combating unwanted plants.

Description

Thiochromanoylcyclohexenone derivatives The present invention relates to novel thiochromanoylcyclohexenone derivatives of the formula I, R~
Ris A ~ S~m Rnz I
'X

where A is C1-C6-alkanediyl, CZ-C6-alkenediyl, C4-C6-alkanedienediyl or CZ-C6-alkynediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
R1 is cyano, thiocyanato, vitro, OR4, SRS, SORE, S02R6, ONR6R~, ON=CR6R8, NR9R1~, P(O)R11R12~ p(g)R11R12~ CORE, C02R6, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three lastmentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: vitro, cyano, C1-Cq-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
RZ is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R3 is hydrogen, halogen or C1-C6-alkyl;
X is oxygen, sulfur, S=0, S(=O)2, CR13R14, C=O or C=NR15 ;
m is 0, 1 or 2;
n is 0, 1, 2, 3 or 4;
R4, RS are one of the radicals mentioned under R6;

~~50/49637 ~ 02355125 2001-06-13 are hydrogen, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-CQ-alkylsulfonyl, Cl-C4-haloalkylsulfonyl, P(O)R11Ri2 or P(S)R11Ri2;
are phenylcarbonyl, phenoxycarbonyl, phenyl-C1-C4-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C1-C4-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R6 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkinyl or C3-C6-cycloalkyl, where the four lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and C1-C4-haloalkoxycarbonyl;
is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R~ is hydrogen or C1-C6-alkyl;
R8 is hydrogen, C1-C6-alkyl, C1-C6-alkoxycarbonyl, cyano or C1-C6-alkoxy;
R9 is one of the radicals mentioned under R4;

0050/49637 ~ 02355125 2001-06-13 is C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, aminocarbonyl, N-C1-C6-alkylaminocarbonyl or N,N-di-(C1-C6-alkyl)aminocarbonyl;
R1~ is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkinyl;
R11, Ri2 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R13~ R14 are hydrogen, nitro, halogen, cyano, C1-C6-alkyl, CI-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, N-C1-C6-alkylamino, N-C1-C6-haloalkylamino, N,N-di(C1-C6-alkyl)amino, N-C1-C6-alkoxyamino, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;
or R13, Ri4 together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R15 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R16 is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl or substituted (1,3-dioxo-2-cyclohexyl)-methylidene;
and their agriculturally useful salts.
Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or to the compositions which comprise them for controlling harmful plants.

0050/49637 ~ 02355125 2001-06-13 Moreover, this invention provides novel intermediates of the formula III, processes for their preparation and a process for preparing compounds of the formula X.
The literature, for example EP-A 283 261, discloses cyclohexanediones which are linked to a bicyclic heterocycle via a carbonyl group. Furthermore, WO 97/09324 describes 2-cyclohexan-1,3-dione thiochromanoyl derivatives and WO 97/30986 2-cyclohexan-1,3-dione-(2',3'-dihydrobenzodithiine) derivatives.
However, the herbicidal properties of the prior art compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel biologically, in particular herbicidally active compounds having improved properties.
This object is achieved by the thiochromanoylcyclohexenone derivatives of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers.
This invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, where the type of salt is usually immaterial. In general, suitable salts are the salts of both cations and the acid addition salts of those acids whose cations and anions, respectively, do not negatively affect the herbicidal activity of the compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where here, if desired, one to four hydrogen atoms may be replaced by C1-Cq-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, _. diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably 5 tri(C1-CQ-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Emphasis is given to the compounds of the formula I according to the invention where R16 is the radical IIa or IIb 8123 ~~
R22 R22- ~~ J .
R21- ~ R21-~~ R17 " ~0 R2 R/19\R18 R2 R19 R18 IIa IIb where:
R17 is hydroxyl, mercapto, halogen, OR24, SR24, SOR25, S02R25, OS02R25, P(O)R26R27, OP(O)R26R27~
p ( S ) R26R27 ~ OP ( S ) R26R27 ~ NR28R29 ~ ONR25R25 or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;

R18, R22 are hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
R19, R21, R23 are hydrogen or C1-C4-alkyl;
R2Q is hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)-methyl,(C1-C6-alkoxy)-(C1-C6-alkylthio)-methyl, di-(C1-C6-alkylthio)methyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-Cg-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, 0050/49637 ~ 02355125 2001-06-13 C1-C6-haloalkylsulfonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl;
is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six lastmentioned radicals may be substituted by one to three C1-C4-alkyl radicals;
or R19 and RZ~ or R2~ and R23 together form a n-bond or a C1-CS-alkyl chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or R19 and R23 together form a C1-C4-alkyl chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or Rz~ and R21 together form a -O-(CHy)p-O-, -O-(CHz)P-S-, -S-(CHZ)p-S-, -O-(CH2)q- or -S-(CH2)9-chain, which may be substituted by one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or R2~ and R21 together with the carbon to which they are attached form a carbonyl group;
R24 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6-haloalkinyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, CZ-C6-alkenylcarbonyl, CZ-C6-alkinylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkinyloxycarbonyl, C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkinylaminocarbonyl, N,N-di(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkinyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, ~~50/49637 ~ 02355125 2001-06-13 N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkinyl)-N-(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-CQ-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N-(C1-C6-alkyl)-N-phenylaminocarbonyl, phenyl-C2-C6-alkenylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N-(C1-C6-alkyl)-N-heterocyclylaminocarbonyl or heterocyclyl-C1-C6-alkenylcarbonyl, where the phenyl or the heterocyclyl radicals of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R25 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkinyl or C3-C6-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-CQ-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or C1-C4-haloalkoxycarbonyl;
is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl or the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following 0050/49637 ~ 02355125 2001-06-13 radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R26, RZ~ are hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, Ci-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R28 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkinyl, C3-C6-haloalkinyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, amino, Ci-C6-alkylamino, di-(C1-C6-alkyl)amino or C1-C6-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl or C3-C6-cycloalkyl;
is phenyl, phenyl-C1-C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C1-C4-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
Rz9 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
p is 2, 3 or 4;
q is 1, 2, 3, 4 or 5.
If R17 = hydroxyl or mercapto ~Y = O, S}, IIa also represents in view the tautomeric forms IIa', IIa " and IIa " ', X050/49637 ~ 02355125 2001-06-13 . a R22-I ~
R21 IIa"
R2 ~~ Y

R23II I~ R23II
R22- , R22 R21- ~ 821-2 YH ~ Y
R
R ~ ~ R1B 2 Rig R18 IIa IIa' I II / l 821 IIa'..
R2 ~ ~ O

and IIb also represents in view the tautomeric forms IIb', IIb "
and IIb" ' .

822 I ~
821 ~ IIb' ' R2 ~~ \O

RI23 I1 ~~
822 ~ 822 O
R2 R2 ~ ~ \ O ~ 821 2 R ~\
819 818 ~~R18 IIb IIb' 822_ 'IIb' ' ' R2 ~ ~ OH

The organic moieties mentioned for the substituents Ri-R29 or as radicals on phenyl-, heterocyclyl and N-heterocyclyl-radicals are individual inumerations of the particular group members. All hydrocarbon chains, i.e. all alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, alkylthio-, haloalkylthio-, alkylsulfinyl-, haloalkylsulfinyl-, alkylsulfonyl-, haloalkylsulfonyl-, N-alkylamino-, N,N-dialkylamino-, N-haloalkylamino-, N-alkoxyamino-, N-alkoxy-N-alkylamino-, alkylcarbonyl-, ~~~~~49637 ~ 02355125 2001-06-13 m haloalkylcarbonyl-, alkoxycarbonyl-, haloalkoxycarbonyl-, alkylthiocarbonyl-, alkylcarbonyloxy-, alkylaminocarbonyl-, dialkylaminocarbonyl-, dialkylaminothiocarbonyl-, dialkoxymethyl-, dialkylthiomethyl-, (alkoxy)(alkylthio)methyl-, 5 alkoxyiminoalkyl-, phenylalkenylcarbonyl-, heterocyclylalkenylcarbonyl-, N-alkoxy-N-alkylaminocarbonyl-, N-alkyl-N-phenylaminocarbonyl-, N-alkyl-N-heterocyclylaminocarbonyl-, phenylalkyl-, heterocyclylalkyl-, phenylcarbonylalkyl-, 10 heterocyclylcarbonylalkyl-, alkoxyalkoxycarbonyl-, alkenylcarbonyl-, alkenyloxycarbonyl-, alkenylaminocarbonyl-, N-alkenyl-N-alkylaminocarbonyl-, N-alkenyl-N-alkoxyaminocarbonyl-, alkynylcarbonyl-, alkynyloxycarbonyl-, alkynylaminocarbonyl-, N-alkynyl-N-alkylaminocarbonyl-, N-alkynyl-N-alkoxyaminocarbonyl-, alkenyl-, alkynyl-, haloalkenyl-, haloalkynyl-, alkenyloxy, alkynyloxy-, alkanediyl, alkenediyl, alkanedienediyl and alkynediyl moieties may be straight-chain or branched. Unless stated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The meaning halogen deals in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:

- C1-C4-alkyl, and the alkyl moieties of phenyl-CF-C4-alkyl and heterocyclyl-C1-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
- C1-C6-alkyl, and the alkyl moieties of C1-C6-alkoxyimino-C1-C6-alkyl, N-C1-C6-alkoxy-N-C1-C6-alkylamino, N-(C1-C6-alkoxy)-N-(C~-C6-alkyl)-aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)-aminocarbonyl, (C3-C6-alkynyl)-N-(C1-C6-alkyl)-aminocarbonyl, N-(C1-C6-alkyl)-N-phenylaminocarbonyl, N-(C1-C6-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl:
C1-C4-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 0050/49637 ~ 02355125 2001-06-13 IZ
_ 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
- C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 1-iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
- C1-C6-haloalkyl, and the haloalkyl moieties of N-c:l-C6-haloalkylamino: C1-C4-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
- C1-C4-alkoxy: for example, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
- C1-C6-alkoxy, and the alkoxy moieties of N-C1-C6-alkoxyamino, di-(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio) methyl, C1-C6-alkoxyimino-C1-C6-alkyl, N-C1-C6-alkoxy-N-C1-C6-alkylamino, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)-aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)-aminocarbonyl and N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)-aminocarbonyl: C1-C4-alkoxy, as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 0050/49637 ~ 02355125 2001-06-13 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
- C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 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-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
- C1-C6-haloalkoxy: C1-C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
- C1-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
- C1-C6-alkylthio: and the alkylthio moieties of C1-C6-alkylthiocarbonyl, di-(C1-C6-alkylthio)methyl and (C1-C6-alkoxy)(C1-C6-alkylthio)methyl: C1-C4-alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, l,l-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, . i 'A I3 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
- C1-C4-haloalkylthio: a C1-C4-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio,-1-(bromomethyl)-2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;
- C1-C6-haloalkylthio: C1-C4-haloalkylthio as mentioned above, and also, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
- C1-C4-alkylsulfinyl (C1-C4-alkyl-S(=O)-): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;
- C1-C6-alkylsulfinyl (C1-C6-alkyl-S(=O)-): C1-C4-alkylsulfinyl as mentioned above, and also pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, m 0050/49637 ~ 02355125 2001-06-13 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
- C1-C4-haloalkylsulfinyl: C1-C4-alkylsulfinyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, ZO 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, Heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;
- C1-C6-haloalkylsulfinyl: C1-C4-haloalkylsulfinyl as mentioned above, and also 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentyisulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
- C1-C4-alkylsulfonyl (C1-C4-alkyl-S(=O)2-): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl;
C1-C6-alkylsulfonyl (C1-C6-alkyl-S(=O)z-): C1-C4-alkylsulfonyl as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, UUSU/49b37 ~ 02355125 2001-06-13 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 5 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;
- C1-C4-haloalkylsulfonyl: a C1-C4-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;
C1-C6-haloalkylsulfonyl: C1-C4-haloalkylsulfonyl as mentioned above, and also 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
- C1-C6-alkylamino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 0050/49637 ~ 02355125 2001-06-13 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
- di-(C1-C4-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino, 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,N-di-(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(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, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
- di-(C1-C6-alkyl)amino: di-(C1-C4-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino.

0050/49637 ~ 02355125 2001-06-13 - - C1-C4-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;
- C1-C6-alkylcarbonyl: CI-C4-alkylcarbonyl, as mentioned above and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2,-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
- C1-C4-haloalkylcarbonyl: a C1-C4-alkylcarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, Heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;

C1-C6-haloalkylcarbonyl: a C1-C4-haloalkylcarbonyl radical as mentioned above, and also 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;
C1-C4-alkoxycarbonyl, and the alkoxy moieties of di-(C1-C4-alkyl)amino-C1-C4-alkoxycarbonyl, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
- C1-C6-alkoxycarbonyl: CI-C4-alkoxycarbonyl, as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl;
- C1-C4-haloalkoxycarbonyl: a C1-C4-alkoxycarbonyl radical as - mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;
- C1-C6-haloalkoxycarbonyl: a C1-C4-haloalkoxycarbonyl radical as mentioned above, and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;
- (C1-C4-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;
(C1-C4-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
- (C1-C6-alkylamino)carbonyl: (C1-C4-alkylamino)carbonyl, as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;

,t 0050/49637 - di-(C1-C4-alkyl)aminocarbonyl: for example, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, 5 N,N-di-(1-methylpropyl)aminocarbonyl, N,N-di-(2-methylpropyl)aminocarbonyl, N,N-di-(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, 10 N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, 15 N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, 20 N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(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, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;
- di-(C1-C6-alkyl)aminocarbonyl: di-(C1-C4-alkyl)aminocarbonyl, as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-(2-methylbutyl)aminocarbonyl, N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl, N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, I5 N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methylpentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1-ethylbutyl)aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;

., 0050/49637 - di-(C1-C6-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl, N,N-di-(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di-(1-methylpropyl)aminothiocarbonyl, N,N-di-(2-methylpropyl)aminothiocarbonyl, N,N-di-(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl, N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N-(1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(2-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylaminothiocarbonyl, N-(2-methylpropyl)-N-propylaminothiocarbonyl, N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbony~l, N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-(1-methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methylpropyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1-methylbutyl)aminothiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-methylpentyl)aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyl, N-methyl-N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothiocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methylpentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;

S

CI-Cq-alkoxy-C1-Cq-alkoxy, and the alkoxyalkoxy moieties of C1-Cq-alkoxy-C1-Cq-alkoxycarbonyl: C1-Cq-alkoxy which is substituted by C1-Cq-alkoxy as mentioned above, i.e., for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)-propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)-propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)-propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)-butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)-butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)-butoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;
- - C3-C6-alkenyl, and the alkenyl moieties of C3-C6-alkenylcarbonyl, C3-C6-alkenyloxy, C3-C6-alkenyloxycarbonyl, C3-C6-alkenylaminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, 2-buten-1-y1, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-i-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 5 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 10 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;
- CZ-C6-alkenyl, and the alkenyl moieties of CZ-C6-alkenylcarbonyl, phenyl-CZ-C6-alkenylcarbonyl and 15 heterocyclyl-C2-C6-alkenylcarbonyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, 20 chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-tri-chloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 25 2,3-dibromobut-2-enyl;
- C3-C6-alkynyl, and the alkynyl moieties of C3-C6-alkynylcarbonyl, C3-C6-alkynyloxy, C3-C6-alkynyloxycarbonyl, C3-C6-alkynylaminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl: for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl;
3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;
- CZ-C6-alkynyl, and the alkynyl moieties of CZ-C6-alkynylcarbonyl: C3-C6-alkynyl as mentioned above, and also ethynyl;

C3-C6-haloalkynyl: a C3-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
- C3-C6-cycloalkyl, and the cycloalkyl moieties of C3-C6-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
- C1-C6-alkanediyl: methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl, 1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3-diyl, pentane-2,2-diyl, 1-methylbutane-1,1-diyl, 1-methylbutane-1,2-diyl, 1-methylbutane-1,3-diyl, 1-methylbutane-1,4-diyl, 2-methylbutane-1,1-diyl, 2-methylbutane-1,2-diyl, 2-methylbutane-1,3-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylpropane-1,1-diyl, 2,2-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,2-diyl, 2,3-dimethylpropane-1,3-diyl, 2,3-dimethylpropane-1,2-diyl, 1,3-dimethylpropane-1,3-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-1,3-diyl, hexane-1,4-diyl-, hexane-1,5-diyl, hexane-1,6-diyl, hexane-2,5-diyl, 2-methylplutane-1,1-diyl, 1-methylpentane-1,2-diyl, 1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl, 1-methylpentane-1,5-diyl, 2-methylpentane-1,1-diyl, 2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl, 2-methylpentane-1,4-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl, 3-methylpentane-1,3-diyl, 3-methylpentane-1,4-diyl, 3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl, 1,1-dimethylbutane-1,3-diyl, 1,1-dimethylbutane-1,4-diyl, 1,2-dimethylbutane-1,1-diyl, 1,2-dimethylbutane-1,2-diyl, 1,2-dimethylbutane-1,3-diyl, 1,2-dimethylbutane-1,4-diyl, 1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl, 1,3-dimethylbutane-1,3-diyl, 1,3-dimethylbutane-1,4-diyl, 1-ethylbutane-1,1-diyl, 1-ethylbutane-1,2-diyl, 1-ethylbutane-1,3-diyl, 1-ethylbutane-1,4-diyl, 2-ethylbutane-1,1-diyl, 2-ethylbutane-1,2-diyl, 2-ethylbutane-1,3-diyl, 2-ethylbutane-1,4-diyl, 2-ethylbutane-2,3-diyl, 2,2-dimethylbutane-1,1-diyl, 2,2-dimethylbutane-1,3-diyl, 2,2-dimethylbutane-1,4-diyl, ~1-isopropylpropane-1,1-diyl, 1-isopropylpropane-1,2-diyl, 1-isopropylpropane-1,3-diyl, 2-isopropylpropane-1,1-diyl, 2-isopropylpropane-1,2-diyl, 2-isopropylpropane-1,3-diyl, 1,2,3-trimethylpropane-1,1-diyl, 1,2,3-trimethylpropane-1,2-diyl or 1,2,3-trimethylpropane-1,3-diyl;
- CZ-C6-alkenediyl: ethene-1,1-diyl, ethene-1,2-diyl, 1-propene-1,1-diyl, 1-propene-1,2-diyl, 1-propene-1,3-diyl, 2-propene-1,1-diyl, 2-propene-1,2-diyl, 2-propene-1,3-diyl, 1-butene-1,1-diyl, 1-butene-1,2-diyl, 1-butene-1,3-diyl, 1-butene-1,4-diyl, 2-butene-1,1-diyl, 2-butene-1,2-diyl, 2-butene-1,3-diyl, 2-butene-1,4-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-methyl-1-propene-1,2-diyl, 1-methyl-1-propene-1,3-diyl, 1-methyl-2-propene-1,1-diyl, 1-methyl-2-propene-1,2-diyl, 1-methyl-2-propene-1,3-diyl, 2-methyl-1,1-propene-1,1-diyl, 2-methyl-1-propene-1,3-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-pentene-1,1-diyl, 1-pentene-1,2-diyl, 1-pentene-1,3-diyl, 1-pentene-1,4-diyl, 1-pentene-1,5-diyl, 1-hexene-1,1-diyl, 1-hexene-1,2-diyl, 1-hexene-1,3-diyl, 1-hexene-1,4-diyl, 1-hexene-1,5-diyl or 1-hexene-1,6-diyl;
- Cz-C6-alkanedienediyl: 1,3-butadiene-1,1-diyl, 1,3-butadiene-1,2-diyl, 1,3-butadiene-1,3-diyl, 1,3-butadiene-1,4-diyl, 1,3-pentadiene-1,1-diyl, 1,3-pentadiene-1,2-diyl, 1,3-pentadiene-1,3-diyl, 1,3-pentadiene-1,4-diyl, 1,3-pentadiene-1,5-diyl, 2,4-pentadiene-1,1-diyl, 2,4-pentadiene-1,2-diyl, 2,4-pentadiene-1,3-diyl, 2,4-pentadiene-1,4-diyl, 2,4-pentadiene-1,5-diyl, 1-methyl-1,3-butadiene-1,4-diyl, 1,3-hexadiene-1,1-diyl, 1,3-hexadiene-1,2-diyl, 1,3-hexadiene-1,3-diyl, 1,3-hexadiene-1,4-diyl, 1,3-hexadiene-1,5-diyl, 1,3-hexadiene-1,6-diyl, 1-methyl-1,3-pentadiene-1,2-diyl, 1-methyl-1,3-pentadiene-1,3-diyl, 1-methyl-1,3-pentadiene-1,4-diyl or 1-methyl-1,3-pentadiene-1,5-diyl;
- CZ-C6-alkynediyl: ethyne-1,2-diyl, 1-propyne-1,3-diyl, 2-propyne-1,1-diyl, 2-propyne-1,3-diyl, 1-butyne-1,3-diyl, 1-butyne-1,4-diyl, 2-butyne-1,1-diyl, 2-butyne-1,4-diyl, 1-methyl-2-propyne-1,1-diyl, 1-methyl-2-propyne-1,3-diyl, 1-pentyne-1,3-diyl, 1-pentyne-1,4-diyl, 1-pentyne-1,5-diyl, 2-pentyne-1,1-diyl, 2-pentyne-1,4-diyl, 2-pentyne-1,5-diyl, 3-pentyne-1,1-diyl, 3-pentyne-1,2-diyl, 3-pentyne-1,5-diyl, 4-pentyne-1,1-diyl, 4-pentyne-1,2-diyl, 4-pentyne-1,3-diyl, 4-pentyne-1,5-diyl, 1-hexyne-1,3-diyl, 1-hexyne-1,4-diyl, 1-hexyne-1,5-diyl, 1-hexyne-I,6-diyl, 2-hexyne-1,1-diyl, 2-hexyne-1,4-diyl, 2-hexyne-1,5-diyl, 2-hexyne-1,6-diyl, 3-hexyne-1,1-diyl, 3-hexyne-1,2-diyl, 3-hexyne-1,5-diyl, 3-hexyne-1,6-diyl, 4-hexyne-1,1-diyl, 4-hexyne-1,2-diyl, 4-hexyne-1,3-diyl, 4-hexyne-1,6-diyl, 5-hexyne-1,1-diyl, 5-hexyne-1,2-diyl, 5-hexyne-1,3-diyl, 5-hexyne-1,4-diyl or 5-hexyne-1,6-diyl;
- heterocyclyl, and the heterocyclyl moieties of heterocyclylcarbonyl, heterocyclyl-C1-C6-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-C1-C6-alkyl, N-(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via carbon and contains one to four identical or different heteroatoms selected from the following group:
oxygen, sulfur or nitrogen, i.e., for example, 5-membered rings having one heteroatom such as, for example:
tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl,tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;
5-membered rings having two heteroatoms, such as, for example, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, - 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-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-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 03-1,2-dithiol-3-yl, 03-1,2-dithiol-4-yl, 03-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-vxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;
5-membered rings having three heteroatoms, such as, for example, 1,2,3-OZ-oxadiazolin-4-yl, 1,2,3-~2-oxadiazolin-5-yl, 1,2,4-04-oxadiazolin-3-yl, 1,2,4-04-oxadiazolin-5-yl, 1,2,4-02-oxadiazolin-3-yl, 1,2,4-OZ-oxadiazolin-5-yl, 1,2,4-03-oxadiazolin-3-yl, 1,2,4-03-oxadiazolin-5-yl, 1,3,4-02-oxadiazolin-2-yl, 1,3,4-OZ-oxadiazolin-5-yl, 1,3,4-03-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 5 1,2,4-04-thiadiazolin-3-yl, 1,2,4-04-thiadiazolin-5-yl, 1,2,4-03-thiadiazolin-3-yl, 1,2,4-03-thiadiazolin-5-yl, 1,2,4-02-thiad'iazolin-3-yl, 1,2,4-02-thiadiazolin-5-yl, 1,3,4-~Z-thiadiazolin-2-yl, 1,3,4-~Z-thiadiazolin-5-yl, 1,3,4-03-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 10 1,3,2-dioxathiolan-4-yl, 1,2,3-02-triazolin-4-yl, 1,2,3-~2-triazolin-5-yl, 1,2,4-~2-triazolin-3-yl, 1,2,4-Oz-triazolin-5-yl, 1,2,4-03-triazolin-3-yl, 1,2,4-03-triazolin-5-yl, 1,2,4-O1-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 15 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 20 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazal-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;
5-membered rings having four heteroatoms, such as, for 25 example, tetrazol-5-yl, 6-membered rings having one heteroatom, such as, for example, tetrahydropyran-2-yl, tetrahydropyran-3-yl, 30 tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, - tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;
6-membered rings having two heteroatoms, such as, for example, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-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, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-I,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5-6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;

., 0050/49637 6-membered rings having three heteroatoms, such as, for example, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl;
6-membered rings having four heteroatoms, such as, for example, 1,2,4,5-tetrazin-3-yl;
where the sulfur of the abovementioned heterocycles may be oxidized to S=0 or S(=0)Z;
and where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C3-C6-carbocycle or another 5-to 6-membered heterocycle.
- N-bonded heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-bonded heterocyclic ring which contains at least one nitrogen and which may contain one to three identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example, N-bonded 5-membered rings having one heteroatom, such as, for example, tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl or pyrrol-1-yl;
N-bonded 5-membered rings having two heteroatoms, such as, for example, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl or imidazol-1-yl;
N-bonded 5-membered rings having three heteroatoms, such as, for example, 1,2,4-04-oxadiazolin-2-yl, 1,2,4-OZ-oxadiazolin-4-yl, 1,2,4-03-oxadiazolin-2-yl, 1,3,4-OZ-oxadiazolin-4-yl, 1,2,4-05-thiadiazolin-2-yl, 1,2,4-03-thiadiazolin-2-yl, 1,2,4-OZ-thiadiazolin-4-yl, 1,3,4-OZ-thiadiazolin-4-yl, 1,2,3-Oz-triazolin-1-yl, 1,2,4-~2-triazolin-1-yl, 1,2,4-~Z-triazolin-4-yl, 1,2,4-~3-triazolin-1-yl, 1,2,4-O1-triazolin-4-yl, 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl;

and also N-bonded 6-membered rings having one heteroatom, such as, for example, piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl or 1,2-dihydropyridin-1-yl; N-bonded 6-membered rings having two heteroatoms, such as, for example, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl, and also N-bonded cyclic imides such as: phthalimide, tetrahydrophthalimide, succinimide, maleinimide or glutarimide.
All phenyl rings or heterocyclyl radicals and also phenyl components in phenyl-alkyl, phenylcarbonyl-alkyl, phenylcarbonyl, phenylalkylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl and phenoxysulfonyl or all heterocyclyl components in heterocyclyl-alkyl, heterocyclylcarbonylalkyl, heterocyclylcarbonyl, heterocyclylalkylcarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylsulfonyl and heterocyclyloxysulfonyl are, unless stated otherwise, preferably unsubstituted or they carry one to three halogen atoms and/or one nitro group, a cyano radical ., 0050/49637 - N-bonded 5-membered rings having four heteroatoms, such as, for example, tetrazol-1-yl;

and/or one or two methyl-, trifluoromethyl-, methoxy- or trifluoromethoxy substituents.
The compounds of the formula I according to the invention where R16 = IIa are referred to as compounds of the formula Ia, and compounds of the formula I where R16 = IIb are referred to as Ib.
With a view to the use of the compounds of the formula I
according to the invention as herbicides, the variables preferably have the following meanings, in each case on their own or in combination:
A is C1-C6-alkanediyl or C2-C6-alkenediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C1-C4-alkoxy, C1-CQ-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
preferably C1-C4-alkanediyl, such as methane-1,1-diyl, ethane-1,1-diyl or ethane-1,2-diyl, or C2-C4-alkenediyl, such as ethene-1,1-diyl, ethene-1,2-diyl, 1-methyl-ethene-1,2-diyl or 1-propene-1,2-diyl;
particularly preferably methane-1,1-diyl or ethene-1,2-diyl;
R1 is cyano, thiocyanato, nitro, OR4, SRS, SORE, SOyR6, ONR6R~, ON=CR6R8, NR9R1~, P(O)R11Ri2~ p(g)Ri1R12~ CORE, COyR6 or N-bonded heterocyclyl, where the lastmentioned radical for its part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
preferably cyano, thiocyanato, nitro, OR4, SRS, SOZR6, ONR6R7, ON=CR6R~, NR9R1~, P(0)RllRlz, p(S)R11R12, CORE, COzR6 or N-bonded heterocyclyl, such as pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-1-yl, pyrrolidin-1-yl, tetrahydroisoxazol-2-yl or morpholin-4-yl;
particularly preferably cyano, nitro, OR4, SOZR6, ONR6R~, p ( 0 ) Ri iRi2 ~ p ( S ) Ri iRi2 ~ COR6 or COZR6 f RZ is C1-C4-alkyl, such as methyl, ethyl, propyl or 1-methylethyl;
R3 is hydrogen, halogen, such as fluorine, chlorine or bromine, or C1-C4-alkyl, such as methyl or ethyl;
particularly preferably hydrogen, chlorine or methyl;
very particularly preferably hydrogen;

X S(=O)2, CRi3Rza or C=O;
preferably S(=0)2 or CR13R14;
m 0, 1 or 2;
preferably 2;
n 0, 1, 2, 3 or 4;
preferably 0,1 or 2;
particularly preferably 0;
R4, R5 are one of the radicals mentioned under R6;
are hydrogen, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-CQ-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, P(O)R11Ri2 or P(S)R11Ri2;
preferably C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkylsulfonyl or C1-CQ-haloalkylsulfonyl;
R6 is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and C1-C4-haloalkoxycarbonyl;
is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl- and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-CQ-alkoxycarbonyl;
is preferably C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy or C1-C4-alkoxycarbonyl;
R~ is hydrogen or C1-C4-alkyl, such as methyl or ethyl;
R8 is hydrogen, C1-C6-alkyl, C1-C6-alkoxycarbonyl or C1-C6-alkoxy;
preferably hydrogen, C1-C4-alkyl or C1-C4-alkoxy;

0050/49637 ~ 02355125 2001-06-13 i R9 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkylcarbonyl, C1-C6-alkoxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy;
R1~ is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R11, Ri2 are hydroxyl, C1-C6-alkyl or C1-C6-alkoxy;
R13, R14 are hydrogen, C1-C6-alkyl or C1-C6-haloalkyl;
preferably hydrogen or C1-C6-alkyl, such as methyl, ethyl or propyl;
or R13, R14 together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, G1-C6-alkoxy or C1-C6-haloalkoxy;
preferably (R13, Ri4) are hydrogen, C1-C4-alkyl such as methyl, ethyl or n-propyl or C1-C4-haloalkyl such as chloromethyl, fluoromethyl or trifluoromethyl;
particularly preferably hydrogen, methyl or ethyl;
R17 is hydroxy, mercapto, halogen, OR24, SR24, SOR25, S02RZS, OSOZRzS, OP(O)R26R27, OP(S)R26R27. NR28R29, ONR25R25 or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C9-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
preferably hydroxyl, mercapto, halogen, ORz4, SR24, S02R25, OSOZR25, NRZBR29, ONR25RZ5 or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
RlB, Rz2 are hydrogen or C1-CQ-alkyl, such as methyl, ethyl or propyl;
preferably hydrogen or methyl;
Ri9 RZ1, R2s are hydrogen or C1-C4-alkyl, such as methyl, ethyl or propyl;
preferably hydrogen or methyl;

R2o is hydrogen, hydroxyl, C1-C6-alkyl, di-(C1-C6-alkoxy)-methyl,(C1-C6-alkoxy)-(C1-C6-alkyl-thio)methyl, di(Cl-C6-alkylthio)methyl, CI-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
is I,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, I,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six lastmentioned radicals may be substituted by one to three C1-C4-alkyl radicals;
is preferably hydrogen, hydroxyl or C1-C4-alkyl, such as methyl, ethyl or propyl;
or R19 and R2~ or R2a and Rz3 together form a n-bond or a C3-CS-alkyl chain Which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or R19 and R23 together form a C1-C4-alkyl chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or R2~ and R21 together form a -O-(CHZ)p-O-, -O-(CHZ)p-S- or -S-(CHZ)p-S chain which may be substituted by one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
preferably, R2~ and R21 together form a -0-(CHZ)p-0-, -O-(CHZ)p-S-or -S-(CHZ)p-S chain which may be substituted by one to three radicals from the following groups: C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
or Rzo and R21 together with the carbon to which they are attached form a carbonyl group;

. 0050/49637 R24 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, 5 C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, N,N-di(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkyl)aminocarbonyl, 10 N-(C1-C6-alkoxy)-N=(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, where the abovementioned 15 alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, hydroxycarbonyl, 20 C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
is phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, 25 phenyl-Cz-C6-alkenylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl or heterocyclyl-C1-C6-alkenylcarbonyl, where the phenyl or 30 the heterocyclyl radical of the 14 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
is preferably C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl or N,N-di(C1-C6-alkyl)aminocarbonyl, where the abovementioned alkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-CQ-alkoxy, C1-CQ-alkylthio or C1-C4-alkoxycarbonyl;
is phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or the heterocyclyl radical of the 10 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R25 is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-cycloalkyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-CQ-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl- or the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
Rzs, R2~ are hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-CQ-haloalkyl, C1-CQ-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
Rz8 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy or di-(C1-C6-alkyl)amino, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl or C3-C6-cycloalkyl;
is phenyl, phenyl-C1-C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C1-C4-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
Rz9 is C1-C6-alkyl or C3-C6-alkenyl;
p is 2, 3 or 4.
Very particularly preference is given to compounds of the formula I where R1 is cyano, thiocyanato, nitro, OR4, S02R6, ONR6R7, ON=CR6R~, NR9R1~, P(O)R11R1z~ p(S)R11R12~ CORE, COzRs or N-bonded heterocyclyl;
R4 C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or C1-C4-haloalkoxycarbonyl;
is CI-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, p(0)RiiRl2 or P(S)R11R12~
is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following - radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl.
Very particular preference is also given to the compounds of the formula I where R1 is cyano, thiocyanato, vitro, SRS, S02R6, ONR6R~, ON=CR6R8, NR9R1~, P(0)RllRlz, p(S)R11R12~ CORE, C02R6 or N-bonded heterocyclyl.
Very particular preference is also given to the compounds of the formula I where R1~ is hydroxyl.
Very particular preference is also given to the compounds of the formula I where R1~ iS halogen, OR24, SRZ4, SOyR25, OS02R25, NRZ$R29, ONR25R2s or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, CI-C4-alkoxy or C1-C4-haloalkoxy.
Very particular preference is also given to the compounds of the formula I where Rle, R2z are hydrogen or C1-C4-alkyl;
R19, R21, R23 are hydrogen or C1-C4-alkyl;
R2~ is hydrogen, hydroxyl, C1-C6-alkyl, di-(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)-(C1-C6-alkylthio)methyl, di-(C1-C6-alkylthio)methyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
in particular hydrogen, hydroxyl or C1-C6-alkyl;
or R19 and R23 together form a C1-C4-alkyl chain which may carry one to three radicals from the following group: halogen, C1-C4-alkyl or C1-C4-haloalkyl;
in particular, R19 and Rz3 together form a methylene bridge which may carry one or two radicals from the following group: halogen, C1-C2-alkyl or C1-C2-haloalkyl;
or Rz~ and RZ1 together with the carbon to which they are attached form a carbonyl group.
Very particular preference is also given to the compounds of the formula I where R18, Rz2 are hydrogen or C1-CQ-alkyl;

Rls~ R21~ R23 are hydrogen or C1-C4-alkyl;
R2° is hydrogen, hydroxyl, C1-C6-alkyl, di-(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)-(C1-C6-alkylthio)methyl, di-(C1-C6-alkylthio)methyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
in particular hydrogen, hydroxyl or C1-C6-alkyl;
or R2° and R21 together with the carbon to which they are attached form a carbonyl group.
Very particular preference is also given to the compounds of the formula I where A is C1-C6-alkanediyl;
particularly preferably methanediyl;
R1 is NO2 , OR4, SRS, SORE , S02R6 , NR9R1°, P ( O ) R11Ri2 or N-bonded heterocyclyl;
particularly preferably OR4, SRS, SORE, SO2R6, P(O)R11Ri2 or N-bonded heterocyclyl, such as, for example, pyrazol-1-yl, 1,2,4-triazol-1-yl or morpholin-4-yl;
very particularly preferably OR4, SRS, S02R6, or P(0)R11R12;
likewise very particularly preferably SRS or S02R6;
likewise very particularly preferably OR4;
R3 is hydrogen;
X is CR13R14, C=O or S02;
particularly preferably CRl3Ria or S02;
very particularly preferably CR13Ri4;
likewise very particularly preferably SO2;
m is 2;
n is O;
R4 is C1-C6-alkyl which may be partially or fully halogenated;

R5 is C1-C6-alkyl, C3-C6-alkenyl or heterocyclyl;
particularly preferably C1-C6-alkyl or C3-C6-alkenyl;
very particularly preferably C1-C6-alkyl;
5 R6 is C1-C6-alkyl or C3-C6-alkenyl, where the two radicals mentioned may be partially or fully halogenated;
particularly preferably C1-C6-alkyl or C3-C6-alkenyl;
very particularly preferably C1-C6-alkyl;
R9 is C1-C6-alkyl, C3-C6-alkenyl or C1-C4-haloalkylcarbonyl;
R1° is C1-C6-alkyl or C3-C6-alkenyl;
R11,R12 are C1-C6-alkyl;
R1~ is hydroxyl;
R1B,R19,Rz°,RZ1,R22,R23 are hydrogen or C1-C4-alkyl;
particularly preferably hydrogen or methyl;
or R2° and RZ1 together with the carbon to which they are attached form a carbonyl group.
Very particular preference is also given to the compounds of the formula Ia.
Most preference is given to the compounds of the formula Ia (=I
where R3, R1g to R23=H, R1~=OH, m=2, n=O), in particular to the compounds Ial.l to Ia1.285, where the radical definitions R1 to Rz3, A, X, m and n have a particular importance for the compounds according to the invention not only in combination with one another, but in each case also on their own.
O O A
SO2~ Ial H~XJ
Table 1 No. A R x Ial.l CHZ NOZ S02 Ial.2 CHZ OCH3 SOZ

45Ial.3 CHZ OCHZCH3 S02 Ial.4 CHy O(CH2)zCH3 SOZ

Ial.S CHZ O(CH2)3CH3 _ No. A Rl g Ial.6 CH2 OCH(CH3)Z_ SOZ
..
~

Ial . 7 CHZ OCH S02 ( CHg ) CH2CH3 Ial.B CH2 OCHZCH(CH3)2 S02 Ial.9 CHZ OC(CH3)3 SOZ

Ia1.10 CH2 OCHZCH=CHy S02 Ial.ll CHy OCH2CH=CH-CH3 S02 Ia1.12 CHy OCH(CH3)CH=CH2 SOZ

Ia1.13 CHz OCHZC.CH SOZ

Ia1.14 CHZ OCH(CH3)C~CH SOy Ia1.15 CHZ OCH2C.C-CH3 SOZ

Ia1.16 CHZ OCHZF SOZ

Ia1.17 CHZ OCHZC1 S02 Ia1.18 CHZ OCF3 S02 Ia1.19 CHZ OCHF2 SOZ

Ia1.20 CHz OCH2CHyF S02 Ia1.21 CH2 OCH2CH2C1 SOZ

Ia1.22 CHz OCHZCF3 S02 Ia1.23 CH2 OCHzCCI3 SOZ

Ia1.24 CHZ OCH2CN S02 Ia1.25 CHZ OCH(CH3)CN S02 Ia1.26 CHZ OCHyC6H5 S02 Ia1.27 CHZ OCH2(furan-2-yl) SOZ

Ia1.28 CHz OCH2(furan-3-yl) - S02 Ia1.29 CH2 SCH3 S02 Ia1.30 CH2 SCHzCH3 S02 Ia1.31 CHy S(CHZ)2CH3 SOZ

Ia1.32 CHy S(CH2)3CH3 S02 Ia1.33 CHZ SCH(CH3)Z S02 Ia1.34 CHZ SCHZCH(CH3)2 SOZ

Ia1.35 CHZ SCHZCH=CH2 SOz Ia1.36 CHZ SCH2C.CH SOZ

Ia1.37 CHZ SC6H5 S02 Ia1.38 CHZ S(4-CH3-C6H4) SOZ

Ia1.39 CHZ S(4-C1-C6H4) SOZ

Ia1.40 CHZ SOyCH3 SOZ

Ia1.41 CHz SOzCHzCH3 SOZ

Ia1.42 CHZ S02(CHZ)zCH3 SOZ

Ia1.43 CHZ SOZ(CH2)3CH3 SOZ

Ia1.44 CHy S02CH(CH3)2 SOZ

Ia1.45 CH2 SOZCH2CH(CH3)z SOz Ia1.46 CHZ SOyCH2CH=CHZ SOZ

Ia1.47 CHz S02CHZC=CH SOZ

Ia1.48 CH2 SOZC6H5 SOZ

Ia1.49 CHy SOy(4-CH3-C6H4) SOZ

Ia1.50 CHz SOZ(4-C1-C6HQ) SOZ

Ia1.51 CHZ S02CF3 S02 Ia1.52 CHZ N(OCH3)CH3 SOZ

Ia1.53 CHZ P(O)(OCH3)y SOy Ia1.54 CHz P(0)(OCHZCH3)z SOy Ia1.55 CHy P(O)(OC6H5)2 SOz Ia1.56 CHz P(O)(CH3)z SOz No . A R~~ g Ia1.57 CHz P(O)(CHyCH3)z SOz ~~

Ia1.58 CHz P(0) SOz (C6H5)2 Ia1.59 CHZ P(S)(OCH3)z SOz Ia1.60 CHz P(S)(OCH2CH3)z SOz Ia1.61 CHz thien-2-yl SOz Ia1.62 CHz morpholin-4-yl SOz Ia1.63 CHz tetrahydroisoxazol-2-yl SOz Ia1.64 CHZ pyrrolidin-1-yl 80z Ia1.65 CHz imidazol-1-yl SOz Ia1.66 CHZ pyrazol-1-yl SOz Ia1.67 CHZ 1,2,4-triazol-1-yl SOz Ia1.68 CHz NOz C(CH3)2 Ia1.69 CHZ OCH3 C(CH3)z Ia1.70 CHz OCH2CH3 C(CH3)z Ia1.71 CHZ O(CHz)zCH3 C(CH3)z Ia1.72 CHz O(CHZ)3CH3 C(CH3)z Ia1.73 CHz OCH(CH3)z C(CH3)z Ia1.74 CHz OCH(CH3)CHZCH3 C(CH3)z Ia1.75 CHz OCH2CH(CH3)z C(CH3)z Ia1.76 CHz OC(CH3)g C(CH3)z Ia1.77 CHz OCH2CH=CHz C(CH3)z Ia1.78 CHZ OCHyCH=CH-CH3 C(CH3)z Ia1.79 CHZ OCH(CH3)CH=CHZ C(CH3)2 Ia1.80 CHz OCHZC.CH C(CH3)z Ia1.81 CHz OCH(CH3)C.CH C(CH3)2 Ia1.82 CHZ OCH2C.C-CH3 C(CH3)z Ia1.83 CHZ OCHyF C(CH3)z Ia1.84 CHz OCHyCl C(CH3)z Ia1.85 CHz OCF3 C(CH3)z Ia1.86 CHz OCHFz C(CH3)z Ia1.87 CHz OCH2CHZF C(CH3)z Ia1.88 CHZ OCHZCH2C1 C(CH3)z Ia1.89 CHZ OCHZCF3 C(CH3)z Ia1.90 CHZ OCHZCC13 C(CH3)z Ia1.91 CHz OCH2CN C(CH3)z Ia1.92 CHZ OCH(CH3)CN C(CH3)z Ia1.93 CHz OCH2C6H5 C(CH3)z Ia1.94 CHz OCHz(furan-2-yl) C(CH3)2 Ia1.95 CHZ OCHz(furan-3-yl) C(CH3)z Ia1.96 CHz SCH3 C(CH3)z Ia1.97 CHZ SCHyCH3 C(CH3)2 Ia1.98 CHz S(CHz)zCH3 C(CH3)z Ia1.99 CHz S(CHz)3CH3 C(CH3)z Ia1.100 CHZ SCH(CH3)z C(CH3)z Ia1.101 CHZ SCH2CH(CH3)z C(CH3)z Ia1.102 CHz SCH2CH=CHz C(CH3)z Ia1.103 CHz SCHZC~CH C(CH3)z Ia1.104 CHZ SC6H5 C(CH3)2 Ia1.105 CHZ S(4-CH3-C6H4) C(CH3)z Ia1.106 CHZ S(4-C1-C6H4) C(CH3)z Ia1.107 CHz SOZCH3 C(CH3)2 No. A R g ~
~~~

Ia1.108 CHZ SOpCHpCH3 C(CH3)2 ~

Ia1.109 CHZ S02(CHZ)2GH3 C(CHg)2 Ia1.110 CHZ SOy(CH2)3CH3 C(CH3)z Ial.lll CH2 S02CH(CH3)Z C(CH3)Z

Ia1.112 CH2 SOZCH2CH(CH3)2 C(CH3)2 Ia1.113 CH2 SOZCHyCH=CH2 C(CH3)2 Ia1.114 CHZ SOyCH2C~GH C(CH3)2 Ia1.115 CH2 SOyC6H5 C(CH3)2 Ia1.I16 CH2 SOy(4-CHg-C6Hq) C(CH3)y Ia1.117 CH2 S02(4-C1-C6Hq) C(CH3)y Ia1.118 CH2 SOZCF3 C(CHg)2 Ia1.119 CH2 N(OCH3)CH3 C(CH3)y Ia1.120 CHZ P(O)(OCH3)z C(CH3)2 Ia1.121 CHz P(O)(OCHZCH3)y C(CH3)2 Ia1.122 CH2 P(O)(OC6H5)2 C(CH3)2 Ia1.123 CHZ P(O)(CH3)y C(CH3)2 Ia1.124 CHZ P(0)(CHZCH3)2 C(CH3)2 Ia1.125 CHz P(O)(C6H5)2 C(CH3)2 Ia1.126 CHz P(S)(OCH3)2 C(CH3)2 Ia1.127 CHZ P(S)(OCHzCH3)2 C(CH3)z Ia1.128 CH2 thien-2-yl C(CH3)2 Ia1.129 CHZ morpholin-4-yl C(CH3)2 Ia1.130 CH2 tetrahydroisoxazol-2-yl C(CH3)2 Ia1.131 CH2 pyrrolidin-1-yl C(CH3)2 Ia1.132 CH2 imidazol-1-yl C(CH3)z Ia1.133 CH2 pyrazol-1-yl C(CH3)2 Ia1.134 CHZ 1,2,4-triazol-1-yl C(CH3)2 Ia1.135 CHZ NOz C=0 Ia1.136 CHZ OCH3 C=O

Ia1.137 CH2 OCHyCH3 C=O

Ia1.138 CH2 O(CH2)ZCH3 C=O

Ia1.139 CHz O(CH2)3CH3 C=0 Ia1.140 CHZ OCH(CH3)2 C=0 Ia1.141 CHz OCH(CHg)CH2CH3 C=O

- Ia1.142 CH2 OCHZCH(CH3)z C=O

Ia1.143 CHZ OC(CH3)3 C=O

Ia1.144 CHy OCHZCH=CHZ C=O

Ia1.145 CHZ OCHZCH=CH-CH3 C=O

Ia1.146 CHz OCH(CH3)CH=CHZ C=0 Ia1.147 CHZ OCHZCgCH C=0 Ia1.148 CHZ OCH(CH3)C$CH C=O

Ia1.149 CHZ OCH2C~C-CH3 C=0 Ia1.150 CHZ OCHyF C=O

Ia1.151 CHy OCHZC1 C=O

Ia1.152 CHZ OCF3 C=O

Ia1.153 CHZ OCHFz C=O

Ia1.154 CHZ OCHZCH2F C=O

Ia1.155 CHy OCHZCHZCl C=O

Ia1.156 CHZ OCHZCF3 C=O

Ia1.157 CHZ OCHzCCI3 C=0 Ia1.158 CHZ OCH2CN C=O

No . A R '- g Ia1.159 CH2 OCH(CH3)CN C=0 Ia1.160 CHZ _ C=O
OCHyC6H5 Ia1.161 CH2 OCHZ(furan-2-yl) C=O

Ia1.162 CH2 OCH2(furan-3-yl) C=0 Ia1.163 CHy SCHg C=0 Ia1.164 CHy SCHyCH3 C=O

Ia1.165 CHy S(CHz)2CH3 C=0 Ia1.166 CH2 S(CH2)3CH3 C=0 Ia1.167 CH2 SCH(CH3)y C=0 Ia1.168 CH2 SCHyCH(CH3)2 C=0 Ia1.169 CHZ SCHyCH=CH2 C=O

Ia1.170 CHZ SCH2C.CH C=0 Ia1.171 CH2 SC6H5 C=O

Ia1.172 CHZ S(4-CH3-C6H4) C=O

Ia1.173 CHZ S(4-C1-C6H4) C=O

Ia1.174 CHy SOyCH3 C=O

Ia1.175 CH2 S02CHZCH3 C=O

Ia1.176 CHy SOZ(CH2)2CH3 C=0 Ia1.177 CH2 SOy(CH2)gCH3 C=O

Ia1.178 CHZ SOyCH(CH3)Z C=O

Ia1.179 CH2 S02CH2CH(CH3)2 C=O

Ia1.180 CH2 S02CHZCH=CHZ C=0 Ia1.181 CHZ SOyCHZCCH C=O

Ia1.182 CH2 S02C6H5 C=0 Ia1.183 CHz SOZ(4-CH3-C6H4) C=O

Ia1.184 CH2 S02(4-C1-C6H4) C=0 Ia1.185 CHZ SOZCF3 C=0 Ia1.186 CH2 N(OCH3)CH3 C=O

Ia1.187 CHZ P(0)(OCH3)2 C=O

Ia1.188 CHz P(O)(OCHZCH3)z C=O

Ia1.189 CHy P(O)(OC6H5)2 C=O

Ia1.190 CH2 P(O)(CH3)2 C=0 Ia1.191 CHy P(O)(CH2CH3)2 C=O

Ia1.192 CHZ P(O)(C6H5)Z C=0 Ia1.193 CHz P(S)(OCH3)2 C=O

Ia1.194 CH2 P(S)(OCHZCH3)2 C=0 Ia1.195 CH2 thien-2-yl C=O

Ia1.196 CH2 morpholin-4-yl C=0 Ia1.197 CHZ tetrahydroisoxazol-2-yl C=0 Ia1.198 CHZ pyrrolidin-1-yl C=0 Ia1.199 CH2 imidazol-1-yl C=0 Ia1.200 CHZ pyrazol-1-yl C=0 Ia1.201 CHy 1,2,4-triazol-1-yl C=O

Ia1.202 CH=CH CN SOZ

Ia1.203 CH=CH NOy SOz Ia1.204 CH=CH SOzCH3 SOZ

Ia1.205 CH=CH SOZCH2CH3 SOZ

Ia1.206 CH=CH SOZ(CH2)zCH3 SOz Ia1.207 CH=CH SOZ(CH2)3CH3 SOy Ia1.208 CH=CH S02CH(CH3)z SOz Ia1.209 CH=CH S02CHzCH(CH3)2 SOy No. A -. R R

Ia1.210 CH=CH ~ SO2 ' '--Ia1.211 CH=CH , SO2 Ia1.212 CH=CH COCH2F SO2 5 Ia1.213 CH=CH COCH2C1 SO2 Ia1.214 CH=CH COCH2Br SO2 Ia1.215 CH=CH COCF3 S02 Ia1.216 CH=CH COCHF2 SO2 Ia1.217 CH=CH C02CH3 S02 Ia1.218 CH=CH C02CH2CH3 Sp2 10 Ia1.219 CH=CH CO2(CH)2CH3 Sp2 Ia1.220 CH=CH CO2(CH2)3CHg SO2 Ia1.221 CH=CH C02CH(CH3)2 SO2 Ia1.222 CH=CH CO2CH2CH(CH3)2 S02 Ia1.223 CH=CH CO2CH2CH2F S02 15 Ia1.224 CH=CH C02CH2CH2C1 S02 Ia1.225 CH=CH CO2CH2CF3 S02 Ia1.226 CH=CH CO2CH2CC13 S02 Ia1.227 CH=CH C02C6H5 Sp2 Ia1.228 CH=CH furan-2-yl S02 Ia1.229 CH=CH thien-2-yl SO2 20 Ia1.230 CH=CH CN C(CH3)2 Ia1.231 CH=CH N02 C(CH3)2 Ia1.232 CH=CH S02CH3 C(CH3)2 Ia1.233 CH=CH S02CH2CH3 C(CH3)2 Ia1.234 CH=CH S02(CH2)2CH3 C(C133)2 25 Ia1.235 CH=CH S02(CH2)3CH3 C(CH3)2 Ia1.236 CH=CH S02CH(CH3)2 C(CH3)2 Ia1.237 CH=CH S02CH2CF~(CH3)2 C(CH3)2 Ia1.238 CH=CH COCH3 C(CH3)2 Ia1.239 CH=CH COCH2CH3 C(CH3)2 Ia1.240 CH=CH COCH2F C(CH3)2 30 Ia1.241 CH=CH COCH2C1 C(CH3)2 Ia1.242 CH=CH COCH2Br C(CH3)2 Ia1.243 CH=CH COCF3 C(CH3)2 Ia1.244 CH=CH COCHF2 C(CH3)2 Ia1.245 CH=CH CO2CH3 C(CH3)2 35 Ia1.246 CH=CH C02CH2CH3 C(CH3)2 Ia1.247 CH=CH C02(CH)2CH3 C(CH3)2 Ia1.248 CH=CH CO2(CH2)3CH3 C(CH3)2 Ia1.249 CH=CH C02CH(CH3)2 C(CH3)2 Ia1.250 CH=CH C02CH2CH(CH3)2 C(CH3)2 Ia1.251 CH=CH C02CH2CH2F C(CH3)2 40 Ia1.252 CH=CH C02CH2CH2C1 C(CH3)2 Ia1.253 CH=CH C02CH2CF3 C(CH3)2 Ia1.254 CH=CH C02CH2CC13 C(CH3)2 Ia1.255 CH=CH C02C6H5 C(CH3)2 Ia1.256 CH=CH furan-2-yl C(CH3)2 45 Ia1.257 CH=CH thien-2-yl C(CH3)2 Ia1.258 CH=CH CN C=O

Ia1.259 CH=CH N02 C=0 Ia1.260 CH=CH S02CH3 C=O

No. A g - x Ia1.261 CH=CH SO2CH2CH3 C=O
~

Ia1.262 CH=CH S02(CH2)2CH3 C=O

Ia1.263 CH=CH SO2(CH2)3CH3 C=O

Ia1.264 CH=CH S02CH(CHg)2 C=O

Ia1.265 CH=CH S02CH2CH(CH3)2 C=0 Ia1.266 CH=CH COCH3 C=O

Ia1.267 CH=CH COCH2CH3 C=0 Ia1.268 CH=CH COCH2F C=0 Ia1.269 CH=CH COCH2C1 C=0 Ia1.270 CH=CH COCH2Br C=0 Ia1.271 CH=CH COCF3 C=O

Ia1.272 CH=CH COCHF2 C=O

Ia1.273 CH=CH C02CH3 C=O

Ia1.274 CH=CH CO2CH2CH3 C=O

Ia1.275 CH=CH C02(CH)2CH3 C=O

Ia1.276 CH=CH C02(CH2)3CH3 C=O

Ia1.277 CH=CH CO2CH(CH3)2 C=O

Ia1.278 CH=CH C02CH2GH(CH3)2 C=O

Ia1.279 CH=CH C02CH2CH2F C=0 Ia1.280 CH=CH C02CH2CH2C1 C=O

Ia1.281 CH=CH C02CH2CF3 C=O

Ia1.282 CH=CH C02CH2CC13 C=0 Ia1.283 CH=CH CO2C6H5 C=O

Ia1.284 CH=CH furan-2-yl C=O

Ia1.285 CH=CH thien-2-yl C=O

Most preference is furthermore given to the following thiochromanoylcyclohexenone derivatives of the formula I:
- the compounds of the formula Ia2, in particular the compounds Ia2.1 to Ia2.285, which differ from the compounds Ial.l to Ia1.285 in that R2~ and R21 are methyl.
R~

I I ~ S02\
OH
Ia2 - the compounds of the formula Ia3, in particular the compounds Ia3.1 to Ia3.285, which differ from the compounds Ial.l to Ia1.285 in that Rzo is methyl.

R~
O O
S0~
OH X
Ia3 - the compounds of the formula Ia4, in particular the compounds Ia4.1 to Ia4.285, which differ from the compounds Ial.l to Ia1.285 in that R22 and R23 are methyl.
R~
O O
s0z\
~5 OH X
Ia4 - the compounds of the formula IaS, in particular the compounds Ia5.1 to Ia5.285, which differ from the compounds Ial.l to Ia1.285 in that R18, R19, R2z and R23 are methyl and R2~ and R2i with the carbon to which they are attached form a carbonyl group.
/R~
O O A
o 'o X
Ia5 - the compounds of the formula Ia6, in particular the compounds Ia6.1 to Ia6.285, which differ from the compounds Ial.l to Ia1.285 in that R1g R19, RZZ and R23 are methyl and R2~ is hydroxyl.
R~
O O p So2~
HO OH ~ X
Ia6 - the compounds of the formula Ia7, in particular the compounds Ia7.1 to Ia7.285, which differ from the compounds Ial.l to Ia1.285 in that R19 and Rz3 together form an ethylene bridge.

~ R~
O O p so \ OH ~ X
Ia7 - the compounds of the formula Ia8, in particular the compounds IaI.l. to Ia8.285, which differ from the compounds Ia.l.l to Ia1.285 in that R19 and R23 together form a methylene bridge.
R~
O O q so OH / X
Ia8 The thiochromanoylcyclohexenone derivatives of formula I can be obtained by various routes, for example by the following processes:
A. Preparation of the compounds of the formula I where R1~=hydroxyl by reaction of an activated carboxylic acid IIIa or a carboxylic acid IIIb, which is preferably activated in situ, with a cyclohexanedione of the formula IV to give the acylation product, followed by rearrangement.

S

~~m ~R2n ~X
IIIb RR23 \ 2 O A~~O~m R2 + L1J ~ 'S 2 R2 O ~ / R n X

IV IIIa Ri O A~
jl \ ~~~m -f-RZ n R23 ~ / ~X

Rls Rls OH O A/
_ R23 R2 \ ~ ~ 2 R2 ~ / R n Rlg ~R18 R3 I (where R1~ = OH) L1 represents a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.
The activated benzoic acid IIIa can be employed directly, as in the case of the benzoyl halides, or generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.
If appropriate, it may be advantageous to carry out the acylation 5 reaction in the presence of a base. Here, the reactants and the auxiliary base are expediently employed in equimolar amounts. A
slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on IIIa or IIIb, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkyl amines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
-If the activated carboxylic acid component used is a benzoyl halide, it may be expedient to cool the reaction mixture to 0-10~C
during the addition of this reaction partner. The mixture is subsequently stirred at 20 - 100~C, preferably at 25 - 50~C, until the reaction has gone to completion. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude ester can be used for the rearrangement without any further purification.
The rearrangement of the esters to the compounds of the formula I
is expediently carried out at 20 - 100~C in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.
Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.
Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or in up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates, preferably in twice the equimolar ratio, based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mole percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilylcyanide, for example in an amount of from 5 to 15, preferably approximately 10, mol percent, based on the ester.
Work-up can be carried out in the manner known per se. The reaction mixer is acidified, for example with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10$
strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the precipitate which forms is filtered off with suction, and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.
B. Preparation of compounds of the formula I where R1~ = halogen by reaction of thiochromanoylcyclohexenone derivatives of the formula I (where R1~=hydroxyl) with halogenating agents:

OH O A~ Ia and/or Ib R23 ~ 101 ~m halogenating Rz ~ ~ S -- (where R1~ = halo-lR2n agent gen) R20 \O / X J

I (where R1~ = OH) Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionylchloride,.oxalylchloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.

C. Preparation of compounds of the formula I where R1~ = OR24, OS02R25, OPOR26Rz~ or OPSRz6Rz~ by reaction of thiochromanoylcyclohexenone derivatives of the formula I
(where R1~=hydroxyl) with alkylating, sulfonylating or phosphonylating agents Va, V~, Vy or V8.

OH O ~1/ L R
R ~~~m Z- 24 Va R2 \ \ ~ or -t-R2n +
RZ O ~ / X L2-S02R25 V~ -~ Ia and/or Ib /~ ( where R1~ = OR24 , Rl~Rla R3 °r OS02R25, OPORz6Rz~
L2-POR26R2~ Vy or OPSR26R27) I (where R1~ = OH) or LZ-PSR26Rz7 V8 LZ is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.
The compounds of the formula Va, V~, Vy or V8 can be employed directly, such as, for example, in the case of the carbonyl halides, or generated in situ, for example activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide, etc.).
D. Preparation of compounds of the formula I where R1~ = OR24, SR24, POR26Rz7, NR2aRZ9, ONR25R25 or N-bonded heterocyclyl by reaction of compounds of the formula I where R17 = halogen, OS02R25 with the compounds of the formula VIa, VI(3, VIy, VIb, VIs or VIr~, if appropriate in the presence of a base or with previous salt formation.

HORZ4 VIGt or Ia and/or Ib (where Ia and/or Ib R1~ = OR24~ gRZ4~
(where Rl~ = halogen, + HSRZ4 VIA ~ PORz6R27 ~ NRzeR29 OSOZRZS ) or ONRZSRzs or N-bonded HPORz6Rz~ MY heterocyclyl ) or HNRz8RZ9 VI8 or HONRZ5R25 VI~
or H ( N-bonded VIr~
heterocyclyl) E. Preparation of compounds of the formula I where R17 = SORZS~
S02Rz5 by reaction of compounds of the formula I where R1~ _ SRzS with an oxidizing agent.
Ia and/or Ib oxidizing agent Ia and/or Ib (where R1~ _ -~ (where R1~ = SORZS, SR25 ) S02RZ5 ) Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxy acetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.
For the reactions mentioned under points B to E, the following conditions apply:
The starting materials are usually employed in equimolar amounts.
However, it may also be advantageous to use an excess of one component or the other.
If appropriate, it may be advantageous to carry out the reactions in the presence of a base. Here, the reactants and the base are expediently employed in equimolar amounts.
With respect to the processes C and D, it may, in certain cases, be advantageous to employ an excess of base, for example from 1.5 to 3 molar equivalents, in each case based on the starting materials.
Suitable bases are tertiary alkyl amines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal - bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, 10 ethers, such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethylsulfoxide, or esters, such as ethyl acetate, or mixtures of these.
15 The reaction temperature is usually in the range from O~C to the boiling point of the reaction mixture.
Work-up can be carried out in a manner known per se to give the product.
Depending on the reaction conditions, in the processes 8 to D the compounds Ia, Ib or mixtures of these may be formed. The latter can be separated by class separation methods, such as, for example, crystallization, chromatography, etc.
The cyclohexanedione of the formula IV used as starting materials are known or can be prepared by processes known per se (for example EP-A 71 707, EP-A 142 741, EP-A 243 313, US 4,249,937, WO 92/13821).
The alkylating agents Va, sulfonylating agents V~, phosphonylating agents Vy or V8, and the compounds VIa, VIA, VIy, VIB, VIe and VI~~
are likewise known, or they can be prepared analogously to known processes.
The carboxylic acid derivatives of the formula III are novel, O A~
~~~m R3" ~ R2 III
n X

where:

A is C1-C6-alkanediyl, CZ-C6-alkenediyl, C4-C6-alkanedienediyl or CZ-C6-alkynediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, 5 C1-C4-alkoxy, Cl-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
R1 is cyano, thiocyanato, vitro, OR4, SRS, SORE, SOZR6, ONR6R~, ON=CR6R8, NR9R1~, P(O)R11R12, p(S)R11R12, CORE, 10 C02R6, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three lastmentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, 15 C1-CQ-alkoxy, C1-CQ-haloalkoxy or C1-C4-alkoxycarbonyl;
R2 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R3 is hydrogen, halogen or C1-C6-alkyl;
X is oxygen, sulfur, S=O, S(=O)2, CR13R14, C=O or C=NR15 ;
m is 0, 1 or 2;
n is 0, 1, 2, 3 or 4;
R4, R5 are one of the radicals mentioned under R6;
are hydrogen, C1-C4-alkylcarbonyl, - C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, P(0)R11R12 or P(S)R11R1z;
are phenylcarbonyl, phenoxycarbonyl, phenyl-C1-C4-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C1-C4-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R6 is CI-C6-alkyl, Cg-C6-alkenyl, C3-C6-alkynyl or C3-C6-cycloalkyl, where the four lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and C1-C4-haloalkoxycarbonyl;
is phenyl, phenyl-CI-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
R~ is hydrogen or C1-C6-alkyl;

is C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, aminocarbonyl, N-C1-C6-alkylaminocarbonyl or N,N-di-(C1-C6-alkyl)aminocarbonyl;
R1~ is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R11~ Ri2 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: vitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-CQ-haloalkoxy or C1-C4-alkoxycarbonyl;
RS is hydrogen, C1-C6-alkyl, C1-C6-alkoxycarbonyl, cyano or C1-C6-alkoxy;
R9 is one of the radicals mentioned under R4;

R13, Ria are hydrogen, vitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, N-C1-C6-alkylamino, N-C1-C6-haloalkylamino, N,N-di(C1-C6-alkyl)amino, N-C1-C6-alkoxyamino, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;
or R13, Ria together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R15 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R3~ is hydroxy or a radical which can be removed by hydrolysis.
Examples of radicals which can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals which may be unsubstituted or substituted, halides, hetaryl radicals which are attached via nitrogen, amino and imino~radicals which may be unsubstituted or substituted, etc.
Preference is given to carbonyl halides of the formula IIIa where R3~=halogen O A~
~~)m Hal I ~ ~R2n IIIa X

where the variables A, X, R1 to R3, m and n are as defined under formula III and Hal is halogen, in particular chloride or bromide.
Likewise, preference is given to carboxylic acids of the formula IIIb 0 A~
(~)m HO I / ~RZn IIIb ~X

where the variables A, X, R1 to R3, m and n are as defined under formula III.
Likewise, preference is given to carboxylic esters of the formula IIIc ~~m ~RZn IIIc ~X
where the variables A, X, R1 to R3, m and n are as defined under formula III and M is C1-C6-alkoxy.
The particularly preferred embodiments of the carboxylic acid derivatives of the formula III with respect to the variables A, X, R1 to R3, m and n correspond to those of the thiochromanoylcyclohexenone derivatives of the formula I.
The carbonyl halides of the formula IIIa (III where R3~=Hal, in particular C1, Br) can be prepared in a manner known per se (cf.
L.G. Fieser, M. Fieser "Reagents for Organic Synthesis", Vol. I, pp. 767-769 (1967)) by reacting the carboxylic acids of the formula IIIb with halogenating agents, such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride or oxalyl bromide.
The benzoic acids of the formula IIIb can be prepared in a known manner by acidic or basic hydrolysis from the corresponding carboxylic esters IIIc (III where M=C1-C6-alkoxy) (J. March, "Advanced Organic Chemistry", 4th Edition, p. 378 ff., Wiley-Interscience Publication, 1992).

0050/49637 ~ 02355125 2001-06-13 The carboxylic esters of the formula IIIc are obtainable by various routes, for example by one of the following processes:
1. Preparation of compounds of the formula IIIc, especially where A=C1-C6-alkanediyl, in particular methanediyl, by reaction of compounds of the formula VII, where L3 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, for example mesylate, haloalkylsulfonate, for example triflate, or cyanide, 0 A~L3 ~Rl (Olm o R1 ~~m 1"~ ' J
--~ ~Rz RZn P(0 alkyl)R11R12 n / X~ or X
P ( S alkyl ) R11R12 VII IIIc with suitable nucleophiles HR1 or phosphites, for example according to Arbuzow (J. March, "Advanced Organic Chemistry", 4th Edition, p. 959, Wiley-Interscience Publication, 1992).
2. Preparation of compounds of the formula IIIc where R1=SORE or S02R6 by reaction of compounds of the formula IIIc where R1=SR6 with an oxidizing agent.
SR6 S(O) 1~ZR6 O A~,O\m 0 A~,O\m w S Z oxidizing agent I"~ w S~-- 2 / X~R n ~ / X~R n IIIc (where R1=SR6) IIIc (where R1=SORE, S02R6) Suitable oxidizing agnets are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacid acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.
3. Preparation of compounds of the formula IIIc where R1=P(S)R11R1z by reaction of compounds of the formula IIIc where R1=P(0)R11R12 with sulfurizing agents, such as P4Slo (cf.
I.W. Still et al., Can. J. Chem. 56, 1423 (1978)), Lawessons Reagent (cf. A. Shabana et al., Chem. Ind. (London) 15, 553 (1984)) or p-toluene disulfide (cf. K. Takuyuki et al., Chem.
Lett. 501 (1986)).
5 pR11R12 pR11R12 ~~m sulfurizing ~ m S agent S
X/ R2n X/ R2n IIIc (where R1=P(0)R11R12) IIIc (where R1=P(S)R11R12) 4. Preparation of compounds of the formula IIIc where A=C2-C6-alkanediyl, C3-C6-alkenediyl, C3-C6-alkinediyl, where the multiple bond is not conjugated to the phenyl ring, by reaction of compounds of the formula VII where L3 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, for example mesylate or haloalkylsulfonate, for example triflate, / /
O A O carbon O A O
~Il~m ~ ~Il~m S R2 nucleophile w S R2 ~ / X~ n ~ / X~ n VII IIIc suitable for this purpose are, for example organometallic reagents, such as Grignard reagents, organolithium or organozinc compounds, or CH-acidic compounds such as aldehydes, ketones, carboxylic acid derivatives (esters, amides, etc.), nitriles, sulfones, 1,3-dithio compounds, diketones, dicarboxylic ester derivatives, ketocarboxylic acid derivatives, dinitriles, ketonitriles, cyanocarboxylic acid derivatives or bisulfones.
If appropriate, it may be advantageous in the reaction with CH-acidic compounds to employ bases, such as alkali metal or alkaline earth metal hydroxides, for example sodium hydroxide or potassium hydroxide, alkali metal or alkaline earth metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal or alkaline earth metal bicarbonates, for example sodium bicarbonate or potassium bicarbonate, alkali metal or alkaline earth metal alkoxides, for example sodium methoxide, sodium ethoxide or potassium tert-butoxide, alkali metal or alkaline earth metal hydrides, for example sodium hydride, or organometallic bases, for example butyllithium.
5. Preparation of compounds of the formula IIIc where A=C2-C6-alkenediyl, in particular where A=C2-C6-alkenediyl, where the double bond is conjugated to the phenyl ring, by reaction of compounds of the formula VII where L3=halogen, in particular bromine, with triarylphosphines, such as triphenylphosphine, and subsequent reaction with appropriately substituted aldehydes or ketones in the presence of bases according to Wittig. Also suitable are related reactions, for example using phosphonates according to Horner-Emmons (cf. J. March, "Advanced Organic Chemistry", 4th Edition, p. 959 ff., Wiley-Interscience Publication, 1992).
By way of example, a Wittig reaction is shown below:
Br ~ ,h3Br-/ ~O~m O
S\ PPh3~ S m / RZn / R2n X
X

VII (where A=CHZ, L3=Br) -~R1 0 -~
R' O ~~ O R
S~m M ~ \ -1-RZn ~ ~X

IIIc (where A=CH=CR'-CHZ) Furthermore, these products can be obtained by using the "inverse starting materials", such as, for example OR..
R\I~Rl Ph P ~R ~ ~ R~.
Sm 3 \R. O ' ~R2n --~ ~O~m X ~ ~ ~- 2 / R n X

VIII (where R"=H, alkyl) IIIc (where A=A'N.~.CR"=CR'-CHZ) 6. Preparation of compounds of the formula IIIc where A=CZ-C6-alkenediyl, in particular where A=Cz-C6-alkenediyl, where the double bond is conjugated to the phenyl radical, by aldol reaction and related reactions in a manner known per se (cf. J. March, "Advanced Organic Chemistry", 4th edition, p.
937, Wiley-Interscience Publication, 1992).
7. Preparation of compounds of the formula IIIc where A=CZ-C6-alkynediyl, in particular where A=Cy-C6-alkynediyl, where the triple bond is conjugated to the phenyl ring, by dehalogenation of compounds of the formula IX using a base, such as alkali metal or alkaline earth metal hydroxides, for example potassium hydroxide, analogously to processes known from the literature (cf. L.I. Smith et al., Org. Synth. 22, 50 (1942); E.V. Dehmlow et al., Liebigs Ann. Chem. 1 (1980)).
Hal Hal ~, ,~ Ri ' / CH-CH-Cy- R1 O A O
0 , ,CX 0 ~ ~S~m MJ ~ S~m base M I j Rz n RZn X

IIIc (where A=CZ-C6-alkynyl) IX (where x+y=0-4) The halides of the formula VII, in particular where A
=methanediyl, and L3=bromine, can be obtained by halogenation of the corresponding alkyl compounds X in the presence of a free radical initiator or by irradiation.

H / hal O1 Ol SJm halogenation SJm X/ R2n X~R2n X VII (where L3=halogen) Suitable halogenating agents are, for example, chlorine, bromine, N-chloroamine, N-chlorosuccinimide, N-bromosuccinimide etc.
Suitable free radical initiators are, inter alia, benzoyl peroxide or azobisisobutyronitrile. However, it is also possible to carry out the reaction under irradiation with suitable radiation sources, such as UV-Hg low pressure or Hg high pressure lamps.
Furthermore, the halides of the formula VII, in particular where A = methanediyl and L3=bromine, can be obtained by halogenation of the corresponding alcohols XI.
OOH / hal S~m halogenation J ~ ~ S~m X~R2n M ~ X~R2n XI VII (where L3=halogen) Suitable halogenating agents are phosphorus pentachloride, phosphorus oxychloride, phosphorus oxybromide, thionyl chloride, thionyl bromide, phosgene, carbonyl bromide, oxalyl chloride, oxalyl bromide, and binary systems, such as carbon tetrachloride/triphenylphosphine or carbon tetrabromide/triphenylphosphine, etc.
The alkyl sulfonates or haloalkyl sulfonates of the formula VII, in particular where A=methanediyl, are obtainable by reaction of alcohols of the formula XI with activated alkyl- or haloalkylsulfonic acids, such as alkyl- or haloalkylsulfonic anhydrides or alkyl- or haloalkylsulfonyl halides.

O~m O~m X~Rzn X/ Rzn VII (where L3=alkyl sulfonate, XI haloalkyl sulfonate)) The aldehydes or ketones of the formula VIII, in particular where A'=a bond can be obtained by oxidation of appropriate compounds of the formula XI in a manner known per se.
/OH / COR"
O A
~ A ~~~m ~ 0 M \ z oxidation J ~ S~m ~-R n M/ \ z X/ ( R n / X

XI VIII
Suitable oxidizing agents are, inter alia, hydrogen peroxide, chromic acid, potassium permanganate, pyridinium dichromate, cerium ammonium nitrate, N-methylmorpholine N-oxide or tetramethylmorpholine N-oxide) cf. J. March, "Advanced Organic Chemistry", 4th Edition, p. 1158 ff., Wiley-Interscience Publication, 1992).
The compounds of the formula IX are prepared by halogenation of the double bond of the compounds of the formula IIIc where A=Cz-C6-alkenediyl, analogously to processes known from the literature (cf. J. March, "Advanced Organic Chemistry", 4th Edition, p. 812 ff., Wiley-Interscience Publication, 1992).
hal hal /CH =CH-Cy- R1 I
O ~'Cx '0/m O ':C~CH-CH-Cy-R1 M J \ S z halogenat~ ~ x ~ / ~R n MJ \ S~ z X ~ -f-R n / ~X
R3 ,, ,, ,, ,, I IIc ( where A= Cx- CH=CH- ~Cy R3 and x+y=O-4) IX (where x+y=O-4) Suitable halogenating agents are, in particular, chlorine or bromine.
The alcohols of the formula XI can be obtained in a manner known 5 per se by reaction of appropriate aldehydes or ketones with carbon nucleophiles. Suitable carbon nucleophiles are, for example, organometallic reagents, such as Grignard reagents, organo lithium or organo tin compounds, but also hydrides (or reducing agents such as lithium aluminum hydride, boranate, etc.
10 or "hydride generating systems", such as hydrogen reductions using a catalyst). This is described below by way of example.
HO R
J ~~ (~)m 15 0 0\/H R,~ M I j X~R2n XI
S~m R3 J
M I \ ~ 2 R n X
20 ~ 0 / OH
R3 ~ ~~~m XII I / Rzn XI
'X

The aldehyde of the formula XII is obtainable by oxidation of compounds of the formula VII where A=methanediyl and L3=chlorine, bromine, in particular bromine.
~ ~ ~~)mr 0 O\/ ~IOI~m M~ \ S 2 oxidizing agent' MJ \ S
~R n ~ ~R2n X
X

VII (where A=CH2, L3=C1 or Br) XII
Suitable oxidizing agents are, inter alia, barium permanganate (Ba(Mn04)2; cf. H. Firouzabadi et al., tetrahedron 46, 6869 (1990)), silver nitrate (AgN03; cf. E. Ghera et al., Synthesis 504 (1984)), potassium dichromate (KZCr20~; cf. E. Santaniello, tetrahedron Lett. 4581 (1979)), bis-(p-methoxyphenyl)selenium oxide (cf. K. Ariyoshi et al., Chem. Lett. 6, 891 (1984)) or isopropyl nitrite (cf. S. Kuriatkowski et al., tetrahedron Lett.
2093 (1990)).

If appropriate, it may be advantageous in the synthesis variants described above to introduce protective groups for certain functionalities if the functionalities are not compatible with the reaction conditions required. The choice of protective groups depends both on the reaction conditions and on the molecular structure. Protective groups, their introduction and removal are generally known from the literature (cf. T.W. Greene et al., "Protective Groups in Organic Synthesis", 2"d Ed., Wiley-New York, 1991) and can be used analogously to processes known from the literature.
Furthermore, it may be necessary to carry out a combination of the synthesis variants described above.
Likewise, it is possible to introduce further substituents or to modify substituents that are already present, by electrophilic, nucleophilic, free-radical or organometallic reactions.
The reactions above are usually carried out at atmospheric pressure.
The reaction temperatures are generally between -100~C and the reflux temperature of the reaction mixture.
In general, solvents or solvent mixtures are used which are suitable for the reaction conditions.
The starting materials are usually employed in stoichiometric amounts. However, it may also be advantageous to use less or more than the stoichiometric amount of one reactant or the other.
Furthermore, the subsequent synthesis of compounds of the formula X (where X=S; m=0) is novel:
H

S
X (X=S; m=0) n In the literature, the synthesis of 5-methyl-2,3-dihydro-1,4-benzodithiine from the cyclic thioketal of 2-methyl-cyclohexanone using N-bromosuccinimide is described.

However, the yield is below 50% (H. Tani et al., heterocycles 36, 1783 (1993)).
It has now been found that the reaction of dithioketals of the formula XIII with a halogenating agent and subsequent treatment with a reducing agent gives satisfactory yields.
H
O A~ R2n O A/ H
S
S
1) halogenating agent ~
-f-R2n 2) reducing agent ~ ~g XIII X (where X=S; m=0) Suitable halogenating agents are, inter alia, N-bromosuccinimide, N-chlorosuccinimide, bromine or chlorine. They are generally employed in a three-fold excess, based on the starting materials.
However, it may also be advantageous to employ a greater or smaller excess. Suitable solvents for the first step of this synthesis are, inter alia, inert solvents, such as halogenated hydrocarbons, for example dichloromethane, trichloromethane, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, etc. or aromatics, such as benzene, toluene or xylene. It may also be advantageous to use solvent mixtures. The reaction temperatures for the first step are generally between -80°C and the reflux temperature of the reaction mixture. The reaction is preferably carried out at from -80°C to room temperature, in particular at from -80°C to 0°C.
Suitable reducing agents are alanates, such as lithium alanate, - diisobutylaluminum hydride, boranates, such as sodium boranate, diborane, metal hydrides, such as trialkyltin hydride, metals, such as zinc, tin, etc. The reducing agent is generally employed in equimolar amounts. However, it may also be advantageous to use more or less than the stoichiometric amount. Suitable solvents for the second reaction step are, in particular, inert solvents, such as ethers, for example diethyl ether, methyl tert-butyl ether or 1,4-dioxane, or dipolar solvents, such as dimethylformamide, diethylformamide, dimethyl sulfoxide, N-methyl pyrrolidone. However, it is also possible to use alcohols, such as methanol, ethanol, etc. The reaction is generally carried out at from 0°C to the reflux temperature of the reaction mixture, preferably at from 0 to 100°C, in particular at from 10 to 40°C.

The preparation of the compounds of the formula XIII from the corresponding cyclohexanone derivatives is carried out by reaction with dithiols, using methods known per se (cf. T.W.
Greene, et al. in "Protective Groups in Organic Synthesis", 2nd Edition, pp. 201-203, Wiley, New York, 1991).
Preparation Examples:
1. 2-~[4,4-dimethyl-8-(4-morpholino)methyl 1,1-dioxothiochroman-7-yl]-carbonyl}-1,3 cyclohexanedione (compound 2.4) Step a) Methyl 3-(3-methyl-2-butenylthio)-2-methylbenzoate 43.5 g (0.275 mol) of 3-methyl-2-butenyl bromide were added dropwise to 50 g (0.275 mol) of methyl 3-thin-2-methyl-benzoate and 37.9 g (0.275 mol) of potassium carbonate in 250 ml of acetone, and the mixture was stirred at room temperature overnight. The solvent was removed, the residue was taken up in water/ethyl acetate and the organic phase was dried and concentrated to dryness.
Yield: 67.9 g (99$) 1H-NMR (CDC13): 8(in ppm) = 7.63 (d, 1H); 7.41 (d, 1H); 7.16 (t, 1H); 5.25 (m, 1H); 3.90 (s, 3H); 3.49 (d, 2H); 2.60 (s, 3H); 1.70 (s, 3H); 1.56 (s, 3H).
Step b) Methyl 4,4,8-trimethylthiochromane-7-carboxylate At -5 to O~C, 206.4 g (1.09 mol) of titanium tetrachloride in 600 ml of methylene chloride were added dropwise to 67.9 g (0.27 mol) of methyl 3-(3-methyl-2-butenylthio)-2-methylbenzoate in 600 ml of methylene chloride and the mixture was subsequently stirred at O~C for 3 hours. The reaction mixture was then poured into a mixture of 1.5 kg of ice and 500 ml of saturated ammonium chloride solution, and the phases that formed were separated. The organic phase was dried and the solvent was removed. The resulting orange oil (62.9 g) was used directly for the next step. For characterization, a sample was chromatographed over silica gel using ethyl acetate/cyclohexane (1:10).
Melting point: 63~C
Step c) Methyl 4,4,8-trimethyl-1,1-dioxothiochromane-7-carboxylate 30.7 g (0.12 mol) of methyl 4,4,8-trimethylthiochromane-7-carboxylate and a spatula tip of sodium tungstate were dissolved in 400 ml of glacial acetic acid and, at 50~C, 31.7 g (0.28 mol) of 30% strength hydrogen peroxide were added dropwise.
The mixture was stirred at this temperature for another 5 hours and subsequently poured into ice-water. The precipitated crystals were filtered off with suction, washed with water and dried.
5 Yield: 31.8 g (91%) Melting point: 151~C
Step d) Methyl 4,4-dimethyl-8-bromomethyl-1,1-dioxothio-chromane-7-carboxylate A little at a time, 20.5 g (0.12 mol) of N-bromosuccinimide were added with UV irradiation to a solution of 31 g (0.11 mol) of methyl 4,4,8-trimethyl-1,1-dioxothiochromane-7-carboxylate in 300 ml of acetonitrile at reflux temperature. At this temperature and under W light, the mixture was stirred for another 1.5 hours and then poured into ice-water. The residue was filtered off with suction, washed with water and dried.
Yield: 36.4 g (92%) Melting point: 163-165~C
Step e) Methyl 4,4-dimethyl-8-(4-morpholino)methyl-1,1-dioxothio-chromane-7-carboxylate (compound 3.18) A little at a time, 0.42 g (17.5 mmol) of sodium hydride was added to a solution of 1.52 g (17.5 mmol) of morpholine in 10 ml of dimethylformamide, and the mixture was stirred at room temperature for another 10 minutes. A solution of 6.0 g (16.6 mol) of methyl 4,4-dimethyl-8-bromomethyl-1,1-dioxothio-chromane-7-carboxylate in 50 ml of dimethylformamide was then added dropwise, and the mixture was stirred for 4 hours. The mixture was poured into ice-water and the resulting precipitate was filtered off with suction, washed with water and dried.
Yield: 5.7 g Melting point: 208-210~C
Step f) 4,4-dimethyl-8-(4-morpholino)methyl-1,1-dioxothio-chromane-7-carboxylic acid (compound 3.19) 0.9 g (22 mmol) of sodium hydroxide was added to a solution of 5.4 g (14.7 mmol) of methyl 4,4-dimethyl-8-(4-morpholino)methyl 1,1-dioxothiochromane-7-carboxylate and 100 ml of a 1/1 methanol/water mixture, and the mixture was heated under reflux for 3 hours. The organic solvent was distilled off and the aqueous phase was acidified using hydrochloric acid and extracted with methylene chloride. The resulting organic phase was dried and concentrated.

Yield: 4.0 g Melting point: 224~C (with decomposition) Step g) 2-{[4,4-dimethyl-8-(4-morpholino)methyl-1,1-dioxothio-5 chroman-7-yl]-carbonyl}-1,3-cyclohexanedione 0.19 g (1.7 mmol) of 1,3-cyclohexanedione, 0.6 g (1.7 mmol) 4,4-dimethyl-8-(4-morpholino)methyl-1,1-dioxothiochromane-7-carboxylic acid and 0.35 g (1.7 mmol) of N,N-dicyclohexylcarbo-10 diimide in 10 ml of acetonitrile was stirred at room temperature overnight. 0.34 g (3.4 mmol) of triethylamine and 0.05 ml of trimethylsilylcyanide were subsequently added, and the mixture was stirred at this temperature for another 3 hours. The mixture was poured into ethyl acetate and sodium carbonate solution, and 15 the aqueous phase was adjusted to pH 2 using hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and the solvent was removed. The residue was chromatographed over silica gel using ethyl acetate/cyclohexane (3:2).
Yield: 0.3 g 20 Melting point: 107~C (with decomposition) 2. 2-[(8-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzo-dithiin-7-yl)carbonyl]-1,3-cyclohexanedione (compound 2.42) 25 Step a) 6-methoxycarbonyl-5-methyl-1,4-dithia-spiro[4,5]-decane Initially 41.0 g (436 mmol) of 1,2-dimercaptoethane and then 6.8 ml of boron trifluoride etherate were added dropwise to a solution of 49.4 g (291 mmol) of 2-methyl-3-oxocyclohexane-30 carboxylate (prepared according to Gupla et al., J. Sci. Ind.
Res. B, 1962, 21, 219) in 200 ml of methylene chloride, and the mixture was stirred at room temperature overnight. 200 ml of 2N
aqueous sodium hydroxide solution were added, the phases were separated, the organic phase was dried over sodium sulfate and 35 the solvent was removed.
Yield: 56.7 g (yellow oil) step b) Methyl 5-methyl-2,3-dihydro-1,4-benzodithiine-6-carboxylate At -78~C, 177.59 g (982 mmol) of N-bromosuccinimide were added to 80.5 g (327 mmol) of 6-methoxycarbonyl-5-methyl-1,4-dithiaspiro-[4,5]-decane in 1200 ml of methylene chloride, and the mixture was stirred at this temperature for a further 30 minutes. The mixture was allowed to warm to room temperature and filtered through silica gel. The filtrate was washed successively with 10~
strength sodium bicarbonate solution and 10$ strength sodium hydrogen sulfide solution, dried over sodium sulfate and concentrated. The residue was subsequently dissolved in 500 ml of dimethylsulfoxide and added dropwise to 14.8 g (390 mmol) of sodium boranate in 200 ml of dimethylsulfoxide. The mixture was stirred for 3 hours, and 100 ml of water were then added dropwise. The mixture was extracted with ethyl acetate and dried over sodium sulfate, and the solvent was removed.
Yield: 54.5 g (yellow oil) 1H-NMR(CDC13): b (in ppm) = 7.45 (d, 1H); 7.05 (d, 1H); 3.84 (s, 3H); 3.37-3.20 (m, 4H); 2.52 (s, 3H).
Step c) Methyl 5-methyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate At 50-60°C, 208 g (1830 mmol) of a 30% strength hydrogen peroxide solution were added dropwise to 100 g (420 mmol) of methyl 5-methyl-2,3-dihydro-1,4-benzodithiine-6-carboxylate in 500 ml of glacial acetic acid and a spatula tip of sodium tungstate, and the mixture was stirred at 50°C for a further 3 hours. The mixture was then poured into water and the resulting precipitate was filtered off with suction. The product was washed successively with sodium bisulfite solution and water and dried under reduced pressure.
Yield: 123 g (colorless solid) 1H-NMR (d6-DMSO): b (in ppm) = 8.10 (d, 1H); 8.04 (d, 1H); 4.42 (m, 4H); 3.90 (s, 3H); 2.75 (s, 3 H).
Step d) Methyl 5-bromomethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate Under reflux and with UV irradiation, 12.9 g (73 mmol) of N-bromosuccinimide were added a little at a time to a suspension of 21 g (69 mmol) of methyl 5-methyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzo-dithiine-6-carboxylate in 200 ml of acetonitrile. After another 6 hours under the abovementioned conditions, the solvent was removed, the residue was stirred with water and the precipitate was filtered off with suction and dried.
Yield: 24.3 g Melting point: 188°C (with decomposition) Step e) Methyl 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro benzodithiine-6-carboxylate (compound 3.30) 0050/49637 ~ 02355125 2001-06-13 At room temperature, 2.35 g (13 mmol) of sodium methoxide in methanol (30% strength solution) were added dropwise to a solution of 5.0 g (13 mmol) of methyl 5-bromomethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate in 50 ml of methanol, and the mixture was subsequently heated to 40~C. After 30 minutes, the solvent was removed, the residue was stirred with water and the aqueous phase was extracted with ethyl acetate. The solvent was removed and the residue was then chromatographed over silica gel.
Yield: 1.4 g (colorless solid) 1H-NMR(CDC13): b (in ppm) = 8.40 (d, 1H); 8.08 (d, 1H); 6.25 (d, 1H); 6.07 (d, 1H); 4.02 (s, 3H); 3.94-3.42 (m, 4H); 3.18 (s, 3H).
Step f) Methyl 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylic acid (compound 3.31) A solution of 1.3 g (3.9 mmol) of methyl 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-benzodithiine-6-carboxylate in a 1:1 mixture of methanol/water was mixed with 0.23 g (5.8 mmol) of sodium hydroxide and heated under reflux for 1 hour. The solvent was removed and the residue was taken up in water and acidified with 2 N hydrochloric acid. The resulting crystalline precipitate was filtered off with suction and dried.
Yield: 0.8 g (colorless solid) 1H-NMR(d6-DMSO): b (in ppm) = 8.40 (d, 1H); 8.18 (d, 1H); 6.18 (d, 1H); 6.08 (d, 1H); 3.80-3.60 (m, 4H); 3.02 (s, 3H).
Step g) 2-[(8-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydrobenzo dithiine-7-yl)-carbonyl]-1,3-cyclohexanedione 0.6 g (1.9 mmol) of 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-benzodithiine-6-carboxylic acid in 20 ml of acetonitrile were admixed with 0.21 g (1.9 mmol) of 1,3-cyclohexanedione and 0.39 g (1.9 mmol) of N,N-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature overnight. 0.38 g (3.8 mmol) of triethylamine and 0.05 ml of trimethylsilyl cyanide were subsequently added, and the mixture was stirred another 3 hours at room temperature. The mixture was poured into a solution of ethyl acetate/sodium carbonate and the precipitate was filtered off with suction. The aqueous phase of the filtrate was then adjusted to pH 3 and extracted with dichloromethane. The organic phase was dried over sodium sulfate and the solvent was removed to give the product.
Yield: 0.45 g (colorless solid) 1H-NMR (CDC13): b (in ppm) = 8.00 (d, 1H); 7.65 (d, 1H); 6.06 (d, 1H); 5.68 (d, 1H); 3.95-3.43 (m, 4H); 3.20 (s, 3H); 2.98-2.40 (m, VVSV/4y63? CA 02355125 2001-06-13 4H); Z.10 (m, 2H).
In addition to the abovementioned thiochromanoylcyclohexenone derivative of the formula I and the carboxylic acid derivatives of the formula III, other compounds which were prepared and are preparable in an analogous manner are listed in Tables 2 and 3 below:

..
..

~, ,n o .
.
rn ~n m ,~
,.
"

.
h O~

tn ~
N

~

..

E

I f~
~
x .-x ~o r, ,-.~

y, 0 b N
r h . O

V ~......... . h ~.
~n .

o - .-a x E N ,-i ~

E ~ ~

U

1 r ~
v p .-mo Tsw x I .r~.~. N .-1 ~

MerODh tnO d'.~N ~

OO N O O r-1O ~-1'~
!n n-in-iriW -1rin-W-1Cp ~
f''1 M

xx v x x x x ~ v xx ~ x x ~ x x ~

xv x v x v ~

y o o o ~ m m x x x x v v v II
M

~ xx V x x v x x ~

N

x xx ~ x x v x x U

~

xx x x x x x x x ~ 00 0 0 0 0 0 0 0 a~

x NN N N N ~ N N N

MfhP'1P7f1f'7f~'7f~'1PI

~ xx x x x x x x x UU V U U U U U U

_ _ _ I"I v r v ~ v v UU U U U U U U U

N~ ~

r rlrl ~ ''1~'1 r'-I~ rl r-Irlrl,~,~1,~1ri~-Ir-1 ~Iref~'1~

!r~'r~r~r~

U ~~ ~ I I I O O O

(~.OO 0 .-1rir-Iw1wlri Q- NN N O O O S-1S-If-I

~~ ~ + +

'' S~ H LLC1Grj ~
.ti.

~,~r?,>-1H N ~'ercr / CL C

Q- W L O O O
m N N N

N

N y --1riri N

z ~N M e~rf1~Oh 0001 N
NN N N N N N N N

.. .. .. . .. .. .. .
x x x ~ ~

x x x ~ OD N M N ~D N v-I tl1 ~ N N

L ~ et' O t0 ts 00 M O

~M w N y ~M w . ~
w ~ ..
d' ~ E m E m ~ E ~ ~
x ~" N ~ I~ v v M v v (~j .~ r-1 \O
w ~1.-. ~ .. ~ ... ~ y . O
.w1 .. .~ ( ~

x er .~ .-. x e-I x 1f1 O ~ ~ .-. ~"~
M \p t!1 '' x x x .-.~ ,.., . x . x . ,-M N N ~-n t~ N M N
M M r-1 .-1 ., .n . .d .. .n ..
, .. ~ .. w ~ ~) ~ v ~ v ~ ~. r ~
[~ ~ ~' ~

1 x -- x x -- x -- x --x x .-~

N N N L!1 ~-1 ~ O N
N l0 M d' M M r-i Cp ~ 1n ..

O . n . ~

~ a~ c~ a~ Tr E ~ ~
E a~ x O v N v ... n v M ...
.. N ~ .~. N N
.~ ..

~. M .. ~ ~ . p w..~ .. ..
(w .. .yp .~

~ x ~ - x a~ -. M
o -. --. .-.
d, w ...

o ~ x x --~ x x x x ,.rC' N N d' N .1 t~ M
t0 .-~ N N
l0 t11 ~ .. . N .. . .. N ~p . . .. . ..

e>'C ~ .~GO .. pl O
~ ~ .
U7 v x ~ x x ~ N v x ~ ~ O ~ v 01 ~ x x ~ N

N m~l O rl f~ODO1N ~ N N rl~-i N x ri O 01 Q~ tD ~ h I~1ppp I O ~O t 1 ~D ri 1 1f1 M .

v ~ v . M 1 I I 1 M 00 . O tf1M . pp Oy e~ v M . .~.
C~

t~ 'C1 ODf~ 'O tf11~N 01~ N ~ ~ erO lWO 'b OD
~ VJ . x r1 v N ODri v ~ t~10I~Cari1~ ~ rir-Iv--Ir-i ri ~ ....t N r 111 v N
W -i !f' x xv x x v x x v x x ~ x x x x x~ x x ~ x x ~ x x ~ x x x x x x x x x x v v v v v O O O O

~ ~ ~ ~

x x x x x x x x x x x U U U U U

r, t~f M ' ,.~

x xx x x x x x x x x x x x x x xx x x x x x x x x x x x x U U U U

x xx x x x x x x x x x x x x ~ 0 00 0 0 0 0 0 0 0 0 0 0 0 0 N NN N N N N N N N N N N N N

P1 f~'7Pt N1f'1~'~1f'1M ~")P'1 f"1f'1P'1P'1 Y~

x xx x x x x x x x x x x x x U_ U_U_ U_U U U U_U_U_ U_U U U U
v v v v v _ U UU U U U U U U U U U U v U U

r-I

I

N

~ ~ N N N

"~x ,.~, ,~

U U U ~ ~.,~.,O M M

P'7 M~'7 N N N ~ x x N fn~'IP7'~'' 'Z'' x xx .-..-..-.U V U ~ x x x U U

x~ x x x '~ O O O O O

U U U U U U ~
.,..~~.

V~V7V1~ V7V7N

C

I

O .wN M C ~f1~Df~0001 O .-~N M er O r-1 r-ir~ r-1rl.-~Irirlriri N N N N N

x .

N NN N N N N N N N N N N N N

.. . .. . p ..
:: .

.. ...

x x x x ~- M x -~ CD N 00 N
~O N

01 O O~ r .. r OD

Gr . ~ . ~ M .. ~
er O ~ ....
~ .

w M m M .~ x 8 x . 8 +~

...rl ...N r N ...1 ~ ~ M

O ..

'I ... ~ 1~ .~ . ~D
p .~ .
!n OD

x l0 x r ~. ~ M
~ O ~ ~ ~1 rl N x N x ~ x x v N N N N .-1 N
rl .-~ N

O

.. ~ ~ .
Vi ~ ~ pp ~ ~ ~
~

a." x Mx ".c x O

I N t0 N tp d' ,1 . .-i ~ ~ ~
M . ~ \p M
~
8 E x E x N

O y. N ~ ..r r N ~
.~. N .-I N
.r ..
. M ..
. ~ .. ~ O .
. ~ M

U ~ '. yo ~ x.x': ~ x x ~

o x ., rr N M N M ~-~ N
N ri N N
~-'~

r t0 jZQ, N . M

p, ~ ~ ~ .-. ~ ,.. M O O
m . .y~ ~
~

-- x -- -- ~n ~ o,U U ~o .- x x -~
x --x d' t0 d' C1 N O .1O O
N

O O tf1 v0 v0 ~ OD .-1 I 'Ly'CS I
tf1 ..

~. M cr I ~ O ~ 1 er ~. N

t0O N N 00N ~O x ~ 00.-101N ~'r-Ir 1p ~ x r Ovr r .~. r ... t000.-1 .-1 01N'-ir r CvO~.-1 N ~. N v N 1D
~

M

x x v x x x x x x xx x x x x x x M

x x v x ac x x x x xx x x x x x M ~~ M M

x v v x x x x x x x ~ ~ ~ ~ ~

II

f~1 f~ f1 n7 f7 fh M

x v v x x ~ x x x x x a ~ ~ ~ ~

x x v x x x x x x xx x x x x x x m x v x x x x m x mx x x x x x x x x x m ~c x x x x xx x m x x x ~ 0 0 0 0 0 0 o o o 00 0 0 o 0 0 N N N N N N N N N NN N N N N N

M fhM M f1 M (~'1P'1 f"1f~M M M f~'1M M

x x x x x x x x x xx x x x x x U_U_U_U_ U_ U_U_U_ U_U_U_U_U_U U U

_ _ _ U U U U U U V U U UV U U V U U

N N N
f1 M N N N ~.L' x M x m x x v x m oex x x x v U U

f'7 ~ ~~ T

N N N N N C"1f'7 _ '' ., ' U V , .Wr ~ ~ ~ N N NN N 1 U
r N N N V U N N x x I I N N

x x x o o x x xx U U U U U V UV x SCU U U

_ _ _ _ N N OO I

V U r O
O O O O O tncl1O O / I N N

~ ~ ~ ~

C>a L~1 ~ tf7 m o r m ov o i N M m vor aoa~o O N N N N N M M M M MM M M M M ~

x N N N N N N N N N NN N N N N N

.
.

o . o ~

a M
o -rl ..

'Z' M
N

~
I
I

.
p ~

N

x ~, .
:, ~

x x ~

L~
r-I
M
N

~
't~
UJ

o x ,.
~..
~.

.

N
.-1 ~

Iff M
N

.
..

~

o~x x x aoao ,-~
er sr x m x m U

x m ~ m ~ 0 0 N

~'~1N

U cn U

w N

CL',M

U

It:N U

x o U

O

-IN

x N N

9959/49637 ~ 02355125 2001-06-13 Table 3:

J~ So2 M I ~ ~ ~ III (where A=CH2, R3=H, m=2, n=0) ~ ~X

po. R M R m.p. [C] or 8-NMR

(8 in ppml 3.1 SCH3 OCH3 C(CH3)27.80 (d, 1H); 7.40 (d, 1H); 4.68 (s, 2H); 3.91 (s, 3H);

3.45 (m, 2H); 2.35 (m, 2H); 2.08 (s, 3H); 1.43 (s, 6H);

3.2 SCH3 OH C(CH3)27.84 (d, 1H); 7.64 (d, 1H); 4.58 (s, 2H); 3.60 (m, 2H);

2.22 (m, 2H); 1.96 (s, 3H); 1.38 (s, 6H);

3.3 SOyCH3 OH C(CH3)2223 3.4 S(CHy)2CH3 OCH3 C(CH3)y87 3.5 S(CHZ)2CH3 OH C(CH3)2163-166 3.6 SOy(CH2)2CH3 OH C(CH3)y158-160 3.7 SCH(CH3)2 OCH3 C(CH3)279-80 3.8 SCH(CH3)y OH C(CH3)2191-192 3.9 SOZCH(CH3)Z OH C(CH3)2239-240 3.10 OCH3 OCH3 C(CH3)2I31-133 3.11 OCH3 OH C(CH3)z227-229 3,12 O(CH2)2CH3 O(CH2)2CH3C(CH3)z7.66 (d, 1H); 7.42 (s, 1H); 5.20 (s, 2H); 4.24 (t, 2H);

3.40 (m, 4H); 2.36 (m, 2H) 1.78 (m, 2H); 1.53 (m, 2H);

1.40 (s, 6H); 1.00 (t, 3H); 0.85 (t, 3H);

3.13 0(CHy)ZCH3 OH C(CH3)2145 3.14 pyrazol-1-yl OCH3 C(CH3)Z171 315 pyrazol-1-yl OH C(CH3)z179 3.16 1,2,4-triazol-1-ylOCH3 C(CH3)28.26 (s, 1H); 7.90 (d, 1H); 7.85 (s, 1H); 7.55 (d, 1H);

6.33 (s, 2H); 3.92 (s, 3H); 3.52 (m, 2H); 2.38 (m, 2H);

1.46 (s, 6H);

3.17 1,2,4-triazol-1-ylOH C(CH3)z265 3.18 morpholin-4-yl OCH3 C(CH3)2208-210 9959/49637 ~ 02355125 2001-06-13 3.19 morpholin-4-yl OH C(CH3)y224 w-w-'.

3.20 S-benzthiazol-2-ylOCH3 C(CH3)2137-138 3.21 S-benzthiazol-2-ylOH C(CH3)2108-109 3.22 P(0)(OCHyCHg)2 OCH3 C(CH3)2789 (d, 1H); 7.40 (d, 1H); 4.50 (d, 2H); 4.12 (m, 2H);

4.06 (m, 2H); 3.97 (s, 3H); 3.42 (m, 2H); 2.38 (m, 2H);

1.42 (s, 6H); 1.24 (t, 6H);

3.23 P(0)(OCHyCH3)Z OH C(CH3)y139-142 3.24 SCHZCH3 OCH3 C(CHg)2128-137 3.25 SCHyCH3 OH C(CH3)2205-208 3.26 S(CH2)3CH3 OCH3 C(CH3)p7.80 (d, 1H); 7.38 (d, 1H); 4.68 (s, 2H); 3.90 (s, 3H);

3.44 (m, 2H); 2.56 (t, 2H); 2.36 (m, 2H); 1.40 (m, lOH); 0.85 (t, 3H);

3.27 SOyCHyCH3 OH C(CH3)Z230 3.28 S(CH2)3CH3 OH C(CH3)Z81-83 3.29 S02(CHZ)gCH3 OH C(CH3)2180-182 3.30 OCH3 OCH3 S02 8.40 (d, 1H); 8.08 (d, 1H); 6.25 (d, 1H); 4.02 (s, 3H);

3.94-3.42 (m, 4H), 3.18 (s, 3H);

3.31 OCH3 OH SOZ 8.40 (d, 1H); 8.18 (d, 1H); 6.18 (d, 1H); 6.08 (d, 1H);

3.80-3.60 (m, 4H);

3.02 (s, 3H);

3.32 N(CH3)(COCFg) OH C(CH3)y203-205 3.33 N(CH3)(COCF3) OCH3 C(CH3)2140-143 3.34 OCHZCH2F OH C(CHg)Z167-168 3.35 OCHZCHZF OCH3 C(CH3)2101 (decomp.) 3.36 N02 OCH3 C(CH3)y154-157 3.37 SOZCHZCH=CHZ OH C(CH3)y63 3.38 SCHZCH=CHZ OH C(CH3)z170-173 3.39 SCHZCH=CH2 OCH3 C(CH3)2134 340 OCHZCF3 OH C(CH3)2184-186 3.41 OCHZCF3 OCH3 C(CH3)294-95 3.42 OCH(CH3)y OH C(CH3)2142-144 3.43 S-(1,2,3-tri- OCH3 C(CH3)259 azol-5-yl) 3.44 N(CHZCH=CHZ)Z OH C(CH3)285 3.45 N(CH2CH=CHZ)z OCH3 C(CH3)269 3.46 N(CH3) OCH3 C(CH3)y116 ._ 9959/49637 3.47 N(CHZCH2CH3)2 OCH3 C(CH3)27.50 (d, 1H); 7.36 (d, 1H); 4.24 (s, 2H); 3.80 (s, 3H);

3.40 (m, 2H); 2.35 (m, 6H); 1.40 (s, 6H); 0.76 (t, 6H);

3.48 S(CH2)2CH3 OH C=O 142-144 3.49 SCHg OCH3 C=0 117-118 10 The compounds of the formula I and their agriculturally useful salts are suitable for use as herbicides, both in the form of isomer mixtures and in the form of the pure isomers. The herbicidal compositions which comprise the compounds of the formula I effect very good control of vegetation on non-crop 15 areas, especially at high rates of application. In crops such as wheat, rice, maize, Soya and cotton, they act against broad-leaved weeds and grass weeds without inflicting substantial damage to the crop plants. This effect is observed mainly at low rates of application.
Depending on the application method in question, the compounds of the formula I, or herbicidal compositions comprising them, can also be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
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, 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), 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, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

.. 9959/49637 ~ 02355125 2001-06-13 In addition, the compounds of the formula I can also be used in crops which, by means of breeding, including genetic engineering methods, have been made tolerant to the action of herbicides.
The compounds of the formula I, or the herbicidal compositions comprising them, can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries which are customary for the formulation of crop protection agents.
Suitable inert auxiliaries are essentially:
mineral oil fractions of medium to high boiling point such as kerosine and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, al)cylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, eg. amines such as N-methylpyrrolidone, 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 dispersions, the thiochromanoylcyclohexenone derivatives of the formula I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and these concentrates are suitable for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg.
ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, of alkyl- and alkylarylsulfonates, of 9959/49637 ~ 02355125 2001-06-13 alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.
Powders, materials for spreading and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
The concentrations of the active compounds of the formula I in the ready-to-use preparations can be varied within wide ranges.
In general, the formulations comprise approximately from 0.001 to 98~ by weight, preferably from 0.01 to 95~ by weight, of at least one active ingredient. The active ingredients are employed in a purity of from 90$ to 100, preferably 95$ to 100 (in accordance with NMR spectra).
The formulation examples which follow illustrate the preparation of such products:
I. 20 parts by weight of compound No. 2.1 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate 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 9959/49637 ~ 02355125 2001-06-13 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
II. 20 parts by weight of compound No. 2.6 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
III. 20 parts by weight of compound No. 2.7 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280~C and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
IV. 20 parts by weight of compound No. 2.11 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 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 gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of Water gives a spray mixture which comprises 0.1% by weight of the active ingredient.
V. 3 parts by weight of compound No. 2.18 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active ingredient.
VI. 20 parts by weight of compound No. 2.20 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 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.

. , 9959/49637 ~ 02355125 2001-06-13 VII. 1 part by weight of compound No. 2.21 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 stable emulsion concentrate.
VIII. 1 part by weight of compound No. 2.24 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol~ EM 31 (= nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.
The compounds of the formula I, or the herbicidal compositions, may be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come in as little contact as possible, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil surface (post-directed, lay-by).
Depending on the control target, the season, the target plants and the growth stage, the rates of application of active compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active substance (a.s.) per ha.
To widen the spectrum of action and to achieve synergistic effects, the thiochromanoylcyclohexenone derivatives of the formula I may be mixed with a large number of representatives of other groups of herbicidal or growth-regulating active ingredients and applied jointly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its 9959/49637 ~ 02355125 2001-06-13 a derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, 5 triazolecarboxamides and uracils.
Furthermore, it may be advantageous to apply the compounds I, alone or in combination with other herbicides, also as a mixture with other crop protection agents, for example with pesticides or 10 agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for remedying nutritional and trace-element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.
Use examples The herbicidal activity of the thiochromanoylcyclohexenone derivatives of the formula I was demonstrated by the following greenhouse experiments:
the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0~ of humous as the substrate.
The seeds of the test plants were sown separately for each species.
In the case of the pre-emergence treatment, the active ingredients, which were suspended or emulsified in water, were planted directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants rooted. This cover caused uniform - germination of the test plants unless this was adversely affected by the active ingredients.
For the post-emergence treatment, the test plants were first grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.25 or 0.125 kg of a.s. (active substance) per ha.
Depending on the species, the plants were kept at from 10 to 25~C
or from 20 to 35~C. The test period extended over 2 to 4 weeks.

9959/49637 ~ 02355125 2001-06-13 ~w During this time, the plants were tended and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth.
The plants used in the greenhouse experiments belonged to the following species:
Scientific Name Common name Avena fatua wild oat Chenopodium album lambsquarter Galium aparine catchweed bedstraw pol onum yg persicaria redshank Sinapis albs white mustard Triticum aestivum spring wheat At application rates of 0.25 or 0.125 kg/ha, the compound 2.13 had very good post-emergence activity against the harmful plants Avena fatua, Galium aparine, Polygonum persicaria and Sinapis alba. Furthermore, the compound 2.25 had very good activity against the weeds Chenopodium album, Polygonum persicaria and Sinapis alba, and it was at the same time compatible with the crop plant Triticum aestivum.

Claims (16)

We claim:
1. A thiochromanoylcyclohexenone derivative of the formula I

where A is C1-C6-alkanediyl, C2-C6-alkenediyl, C4-C6-alkanedienediyl or C2-C6-alkynediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;

R1 is cyano, thiocyanato, nitro, OR4, SR5, SOR6, SO2R6, ONR6R7, ON=CR6R8, NR9R10, P(O)R11R12, p(S)R11R12, COR6, CO2R6, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three lastmentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R2 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;

R3 is hydrogen, halogen or C1-C6-alkyl;

X is oxygen, sulfur, S=O, S(=O)2, CR13R14, C=O or C=NR15;

m is 0, 1 or 2;

n is 0, 1, 2, 3 or 4;

R4, R5 are one of the radicals mentioned under R6;

are hydrogen, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, P(O)R11R12 or P(S)R11R12;

are phenylcarbonyl, phenoxycarbonyl, phenyl-C1-C4-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C1-C4-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R6 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C3-C6-cycloalkyl, where the four lastmentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and C1-C4-haloalkoxycarbonyl;

is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R7 is hydrogen or C1-C6-alkyl;

R8 is hydrogen, C1-C6-alkyl, C1-C6-alkoxycarbonyl, cyano or C1-C6-alkoxy;

R9 is one of the radicals mentioned under R4;

is C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, aminocarbonyl, N-C1-C6-alkylaminocarbonyl or N,N-di-(C1-C6-alkyl)aminocarbonyl;

R10 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;

R11, R12 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R13, R14 are hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, N-C1-C6-alkylamino, N-C1-C6-haloalkylamino, N,N-di(C1-C6-alkyl)amino, N-C1-C6-alkoxyamino, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;

or R13, R14 together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;

R15 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;

R16 is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl or substituted (1,3-dioxo-2-cyclohexyl)-methylidene;

and its agriculturally useful salts.
2. A thiochromanoylcyclohexenone derivative of the formula I as claimed in claim 1 in which R16 is the radical IIa or IIb, where R17 is hydroxyl, mercapto, halogen, OR24, SR24, SOR25, SO2R25, OSO2R25, P(O)R26R27, OP(O)R26R27, P(S) R26R27, OP (S)R26R27, NR28R29, ONR25R25 or N-bonded heterocyclyl, which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
R18, R22 are hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;

R19, R21, R23 are hydrogen or C1-C4-alkyl;

R20 is hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl;
di-(C1-C6-alkoxy)-methyl,(C1-C6-alkoxy)-(C1-C6-alkylthio)-methyl, di-(C1-C6-alkylthio)methyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl;

is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six lastmentioned radicals may be substituted by one to three C1-C4-alkyl radicals;

or R19 and R20 or R20 and R23 together form a .pi.-bond or a C1-C5-alkyl chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;

or R19 and R23 together form a C1-C4-alkyl chain which may carry one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;

or R20 and R21 together form a -O-(CH2)p-O-, -O-(CH2)p-S-, -S-(CH2)p-S-, -O-(CH2)q- or -S-(CH2)q-chain, which may be substituted by one to three radicals from the following group: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;

or R20 and R21 together with the carbon to which they are attached form a carbonyl group;

R24 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, N,N-di(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkynyT)-N-(C1-C6-alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl, di-(C1-C6-alkyl)aminothiocarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C1-C4-alkoxy, C1-C4-alkylthio, di-(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;

is phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N-(C1-C6-alkyl)-N-phenylaminocarbonyl, phenyl-C2-C6-alkenylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N-(C1-C6-alkyl)-N-heterocyclylaminocarbonyl or heterocyclyl-C1-C6-alkenylcarbonyl, where the phenyl or the heterocyclyl radicals of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;

R25 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C3-C6-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or C1-C4-haloalkoxycarbonyl;

is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl or the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R26, R27 are hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;

R28 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)amino or C1-C6-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl or C3-C6-cycloalkyl;

is phenyl, phenyl-C1-C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C1-C4-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;

R29 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;

p is 2, 3 or 4;

q is 1, 2, 3, 4 or 5.
3. A process for preparing compounds of the formula I where R17=hydroxyl as claimed in claim 1 or 2, which comprises acylating a cyclohexane-1,3-dione with an activated carboxylic acid IIIa or a carboxylic acid IIIb, where the variables R1 to R3, A, X, m and n are as defined in claim 1 and L1 is a nucleophilically replaceable leaving group and rearranging the acylation product in the presence of a catalyst to give the compounds I where R17 = hydroxyl.
4. A process for preparing compounds of the formula I where R17 =
halogen as claimed in claim 1 or 2, which comprises reacting a thiochromanoylcyclohexenone derivative of the formula I
where R17 = hydroxyl with a halogenating agent.
5. A process for preparing compounds of the formula I where R17 =
OR24, OSO2R25, OPOR26R27 or OPSR26R27, as claimed in claim 1 or 2, which comprises reacting a thiochromanoylcyclohexenone derivative of the formula I where R17 = hydroxyl with an alkylating agent V.alpha., sulfonylating agent V.beta. or phosphonylating agent V.gamma. or V.delta., V.alpha. V.beta. V.gamma.
V.delta.

where the variables R24 to R27 are as defined in claim 2 and L2 is a nucleophilically replaceable leaving group.
6. A process for preparing compounds of the formula I where R17 =
OR24, SR24, POR26R27, NR28R29, ONR25R25 or N-bonded heterocyclyl as claimed in claim 1 or 2, which comprises reacting a thiochromanoylcyclohexenone derivative of the formula I where R17 = halogen or OSO2R25, with a compound of the formula VI.alpha., VI.beta., VI.gamma., VI.delta., VI.epsilon. or VI~, VI.alpha. VI.beta. VI.gamma. VI.delta.
VI.epsilon.

H(N-bonded heterocyclyl) VI~, where the variables R24 to R29 are as defined in claim 2, if appropriate in the presence of a base.
7. A process for preparing compounds of the formula I where R17 =
SOR25, SO2R25 as claimed in claim 1 or 2, which comprises reacting a compound of the formula I where R17 = SR25 with an oxidizing agent.
8. A composition, comprising a herbicidally effective amount of at least one thiochromanoylcyclohexenone derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 or 2, and auxiliaries which are customarily used for formulating crop protection agents.
9. A process for preparing compositions as claimed in claim 8, which comprises mixing a herbicidally effective amount of at least one thiochromanoylcyclohexenone derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 or 2 and auxiliaries which are customarily used for the formulation of crop protection agents.
10. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one thiochromanoylcyclohexenone derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 or 2 to act on plants, their habitat and/or on seeds.
11. The use of thiochromanoylcyclohexenone derivatives of the formula I or agriculturally useful salts thereof as claimed in claim 1 or 2 as herbicides.
12. A carboxylic acid derivative of the formula III, where R30 is hydroxyl or a radical that can be removed by hydrolysis and the variables R1 to R3, A, X, m and n are as defined in claim 1.
13. A carboxylic acid derivative of the formula III as claimed in claim 12, where R30 is halogen, hydroxyl or C1-C6-alkoxy.
14. A process for preparing the compounds of the formula IIIc where A=C1-C6-alkanediyl and M=C1-C6-alkoxy, as claimed in claim 12 or 13, which comprises reacting a compound of the formula VII, where L3 is a nucleophilically replaceable leaving group with nucleophiles HR1, if appropriate in the presence of a base, or phosphites P(Oalkyl)R11R12 or P(Salkyl)R11R12.
15. A process for preparing compounds of the formula IIIc where A
= C2-C6-alkanediyl, C3-C6-alkenediyl or C3-C6-alkynediyl and M=C1-C6-alkoxy as claimed in claim 12 or 13, which comprises reacting a compound of the formula VII (carbon chain length of A'= carbon chain length of A-1), where L3 is a nucleophilically replaceable leaving group with a carbon nucleophile.
16. A process for synthesizing compounds of the formula X (where X=S and m=0), which comprises reacting a compound of the formula XIII with a halogenating agent and subsequently with a reducing agent, where the variables R2, R3, A, m and n are as defined in claim 12 or 13.
CA002355125A 1998-12-15 1999-12-02 Thiochromanoylcyclohexenone derivatives Abandoned CA2355125A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19857898 1998-12-15
DE19857898.9 1998-12-15
PCT/EP1999/009395 WO2000035903A2 (en) 1998-12-15 1999-12-02 Thiochromanoyl cyclohexenone derivatives

Publications (1)

Publication Number Publication Date
CA2355125A1 true CA2355125A1 (en) 2000-06-22

Family

ID=7891190

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002355125A Abandoned CA2355125A1 (en) 1998-12-15 1999-12-02 Thiochromanoylcyclohexenone derivatives

Country Status (5)

Country Link
EP (1) EP1144401A3 (en)
JP (1) JP2002532489A (en)
AU (1) AU1969300A (en)
CA (1) CA2355125A1 (en)
WO (1) WO2000035903A2 (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19532311A1 (en) * 1995-09-01 1997-03-06 Basf Ag Benzoyl derivatives
PL328505A1 (en) * 1996-02-24 1999-02-01 Basf Ag 2-heteroaroylcyclohexano-1,3-diones

Also Published As

Publication number Publication date
AU1969300A (en) 2000-07-03
EP1144401A3 (en) 2002-09-11
EP1144401A2 (en) 2001-10-17
WO2000035903A2 (en) 2000-06-22
WO2000035903A3 (en) 2001-10-18
JP2002532489A (en) 2002-10-02

Similar Documents

Publication Publication Date Title
AU742514B2 (en) 4-(3-heterocyclyl-1-benzoyl)pyrazoles and their use as herbicides
US6541423B1 (en) 4-(3′,4′-heterocyclyl benzoyl) pyrazoles as herbicidal agents
US6589915B1 (en) Benzohetero cyclylcyclo hexenones and their use as herbicides
US7115545B1 (en) Tricyclic benzoylpyrazole derivatives used as a herbicide
US6908884B2 (en) Benzazolonylcarbonylcyclohexenones and their use as herbicides
US6613717B1 (en) Phosphoric benzoyl derivatives and their use as herbicides
US6326333B1 (en) Pyrazolyldioxothiochromanoyl derivatives
US6440899B1 (en) Cyclohexenonedioxothiochromanoyl derivatives
US7030063B1 (en) Cyclohexenonquinolinoyl-derivatives as herbicidal agents
US6583089B1 (en) Tricyclic benzoylcyclohexanedione derivatives
US6352959B1 (en) Thiochromanoylpyrazolone derivatives
US6667333B2 (en) Herbicidal 3-(4,5 dihydroisoxazole- 3 yl) substituted benzoycyclohexenone derivatives
US20040033899A1 (en) 5[(pyrazol-4-yl)carbonyl]benzazolone as herbicide
US6599860B1 (en) Herbicidal halogenalkyl-substituted 3-(4,5-dihydroisoxazol-3-yl)-benzoyl-cyclohexenones
CA2355125A1 (en) Thiochromanoylcyclohexenone derivatives
MXPA00010574A (en) Cyclohexenondioxothio chromanoyl derivatives

Legal Events

Date Code Title Description
FZDE Discontinued