U.S. patent application number 10/276225 was filed with the patent office on 2003-10-23 for 3-(4,5-dihydroisoxaxol-5-yl)benzoylcyclohexenones and the use thereof as herbicides.
Invention is credited to Baumann, Ernst, Deyn, Wolfgang von, Kudis, Steffen, Langemann, Klaus, Mayer, Guido, Misslitz, Ulf, Neidlein, Ulf, Walter, Helmut, Witschel, Matthias, Zagar, Cyrill.
Application Number | 20030199699 10/276225 |
Document ID | / |
Family ID | 7642351 |
Filed Date | 2003-10-23 |
United States Patent
Application |
20030199699 |
Kind Code |
A1 |
Baumann, Ernst ; et
al. |
October 23, 2003 |
3-(4,5-Dihydroisoxaxol-5-yl)benzoylcyclohexenones and the use
thereof as herbicides
Abstract
The invention relates to
3-(4,5-dihydroisoxazole-5-yl)benzoylcyclohexenone- s of the general
formula (I), wherein the variables have the following meanings:
R.sup.1, R.sup.2 represents hydrogen, nitro, halogen, cyano, alkyl,
haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio,
alkylsulfinyl, haloalkylsulfinyl, alkysulfonyl or C.sub.1-C.sub.6
haloalkylsulfonyl; R.sup.3 represents hydrogen, halogen or alkyl;
R.sup.4 represents hydrogen or alkyl; R.sup.5, R.sup.6 represents
hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio,
dialkylamino, phenyl, benzyl or carbonyl, wherein the 7 last
residues can be substituted; R.sup.11 represents optionally
substituted cyclohexenone that is linked in the 2 position and that
carries a hydroxy residue or derivatives thereof in the 1 position.
The invention further relates to the agriculturally useful salts
thereof, to methods for producing the
3-(4,5-dihydroisoxazole-5-yl)benzoylcyclohexenones, to agents that
contain the inventive compound, and to the use of said derivatives
or agents containing them for controlling undesired plants.
Inventors: |
Baumann, Ernst; (Dudenhofen,
DE) ; Deyn, Wolfgang von; (Neustadt, DE) ;
Kudis, Steffen; (Mannheim, DE) ; Langemann,
Klaus; (Schauenburg, DE) ; Mayer, Guido;
(Neustadt, DE) ; Misslitz, Ulf; (Neustadt, DE)
; Neidlein, Ulf; (Mannheim, DE) ; Walter,
Helmut; (Obrigheim, DE) ; Zagar, Cyrill;
(Ludwigshafen, DE) ; Witschel, Matthias;
(Durkheim, DE) |
Correspondence
Address: |
KEIL & WEINKAUF
1350 CONNECTICUT AVENUE, N.W.
WASHINGTON
DC
20036
US
|
Family ID: |
7642351 |
Appl. No.: |
10/276225 |
Filed: |
November 14, 2002 |
PCT Filed: |
May 11, 2001 |
PCT NO: |
PCT/EP01/05390 |
Current U.S.
Class: |
548/237 |
Current CPC
Class: |
A01N 43/80 20130101;
C07D 261/04 20130101; C07D 261/20 20130101 |
Class at
Publication: |
548/237 |
International
Class: |
C07D 263/08 |
Foreign Application Data
Date |
Code |
Application Number |
May 18, 2000 |
DE |
100 24 107.7 |
Claims
We claim:
1. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I 187in which the variables have the following meanings:
R.sup.1, R.sup.2 are hydrogen, nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or C.sub.1-C.sub.6-haloalkylsulfonyl;
R.sup.3 is hydrogen, halogen or C.sub.1-C.sub.6-alkyl; R.sup.4 is
hydrogen or C.sub.1-C.sub.4-alkyl; R.sup.5, R.sup.6 are hydrogen,
halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkoxy)-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alky- l)amino-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1- -C.sub.4-alkyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; or R.sup.5 and R6 together form a
C.sub.2-C.sub.6-alkanediyl chain which can be mono-to
tetrasubstituted by C.sub.1-C.sub.4-alkyl and/or can be interrupted
by oxygen or by unsubstituted or C.sub.1-C.sub.4-alkyl-substituted
nitrogen; R.sup.7 is halogen, cyano, hydroxyl,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalky- l,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl,
amino, C.sub.1-C.sub.6-alkylamino, di(C.sub.1-C.sub.6-alkyl)amino,
di(C.sub.1-C.sub.4-alkoxy)methyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl or COR.sup.8;
R.sup.8 is hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, hydroxyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy or NR.sup.9R.sup.10; R.sup.9 is hydrogen
or C.sub.1-C.sub.4-alkyl; R.sup.10 is C.sub.1-C.sub.4-alkyl;
R.sup.11 is a cyclohexenone of the formula II 188which is linked in
the 2-position and where R.sup.12 is hydroxyl, mercapto, halogen,
OR.sup.19, SR.sup.19, SOR.sup.20 or SO.sub.2R.sup.20; R.sup.13,
R.sup.17 are hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio or C.sub.1-C.sub.4-alkoxycarbonyl;
R.sup.14, R.sup.16, R.sup.18 are hydrogen or C.sub.1-C.sub.4-alkyl;
R.sup.15 is hydrogen, hydroxyl, halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alko- xy)methyl,
(C.sub.1-C.sub.6-alkoxy) (C.sub.1-C.sub.6-alkylthio)methyl,
di(C.sub.1-C.sub.6-alkylthio)methyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-haloalkoxycarbonyl, 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, it being possible for the
six last-mentioned radicals to have attached to them one, two or
three substituents selected from amongst C.sub.1-C.sub.4-alkyl; or
.sup.13 and R.sup.14 or R.sup.17 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl; R.sup.14 and R.sup.15 or R.sup.15
and R1.sup.8 together are a chemical bond or
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl; or R.sup.14 and R.sup.18 together
are C.sub.1-C.sub.5-alkanediyl which can have attached to it one,
two or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl; or R.sup.15 and R.sup.16 together
are --O--(CH.sub.2).sub.p--O--, --O--(CH.sub.2).sub.p--S--,
--S--(CH.sub.2).sub.p--S--, --O--(CH.sub.2).sub.q-- or
--S--(CH.sub.2).sub.q--, each of which can have attached to it one,
two or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl; or R.sup.15 and R.sup.16 together
are an oxygen atom; R.sup.19 is C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl,
C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.20-alkylcarbonyl, C.sub.2-C.sub.20-alkenylcarbonyl,
C.sub.2-C.sub.6-alkynylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl,
C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminoc- arbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbo-
nyl,
N-(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N-(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl,
C.sub.1-C.sub.6-alkoxyimi- no-C.sub.1-C.sub.6-alkyl, it being
possible for the abovementioned alkyl, alkoxy and cycloalkyl
radicals to be partially or fully halogenated and/or to have
attached to them one, two or three substituents selected from
amongst cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-al- koxycarbonyl,
C.sub.1-C.sub.4-alkylaminocarbonyl, N,N-di(C.sub.1-C.sub.4-a-
lkyl)aminocarbonyl or C.sub.3-C.sub.6-cycloalkyl; phenyl,
phenyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, heterocyclyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-- alkyl, heterocyclylcarbonyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, it being
possible for the phenyl or heterocyclyl radical of the
abovementioned radicals to be partially or fully halogenated and/or
to have attached to it one, two or three substituents selected from
amongst nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; R.sup.20 is C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl,
C.sub.3-C.sub.6-alkynyl or C.sub.3-C.sub.6-cycloalkyl, it being
possible for the abovementioned alkyl and cycloalkyl radicals to be
partially or fully halogenated and/or to have attached to them one,
two or three substituents selected from amongst cyano,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkylaminocarbonyl,
N,N-di(C.sub.1-C.sub.4-alkyl)aminocar- bonyl or
C.sub.3-C.sub.6-cycloalkyl; phenyl, phenyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl-C.sub.1-C.sub.6-alkyl, heterocyclyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl or
heterocyclylcarbonyl-C.sub.1-C.sub.- 6-alkyl, it being possible for
the phenyl or heterocyclyl radical of the abovementioned radicals
to be partially or fully halogenated and/or to have attached to it
one, two or three substituents selected from amongst nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; p is 2, 3 or
4; q is 1, 2, 3, 4 or 5; or an agriculturally useful salt
thereof.
2. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in claim 1, where R.sup.1, R.sup.2 are nitro,
halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl.
3. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in claim 1 or 2, where R.sup.3 is
hydrogen.
4. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in any of claims 1 to 3, where R.sup.5 is
hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub- .4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups: nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy; R.sup.6 is hydrogen or
C.sub.1-C.sub.4-alkyl.
5. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in any of claims 1 to 4, where R.sup.5 and
R.sup.6 are hydrogen.
6. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in any of claims 1 to 5, where R.sup.12 is
hydroxyl, OR.sup.19 or SR.sup.19; and R.sup.19 is
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.20-alkylc- arbonyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl-
, it being possible for the alkyl and alkoxy radicals to be
partially or fully halogenated and/or to have attached to them one,
two or three substituents selected from amongst cyano,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl or
C.sub.3-C.sub.6-cycloalkyl; phenyl, phenyl-C.sub.1-C.sub.4-alkyl,
phenylcarbonyl-C.sub.1-C.sub.4-alkyl, phenylcarbonyl,
phenoxycarbonyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub-
.4-alkyl, heterocyclylcarbonyl-C.sub.1-C.sub.4-alkyl,
heterocyclyloxycarbonyl, it being possible for the phenyl or
heterocyclyl radical of the abovementioned radicals to be partially
or fully halogenated and/or have attached to it one, two or three
substituents selected from amongst nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy.
7. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in any of claims 1 to 6, where R.sup.12 is
hydroxyl.
8. A 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I as claimed in any of claims 1 to 7, where R.sup.13 and
R.sup.17 independently of one another are hydrogen,
C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkylthio; R.sup.14,
R.sup.16, R.sup.18 independently of one another are hydrogen or
methyl; R.sup.15 is hydrogen, hydroxyl, C.sub.1-C.sub.6-alkyl or
di(C.sub.1-C.sub.6-alkoxy)methyl; or R.sup.13 and R.sup.14 or
R.sup.14 and R.sup.15 or R.sup.15 and R.sup.18 or R.sup.14 and
R.sup.18 or R.sup.17 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl; or R.sup.15 and R.sup.16 together
are an oxygen atom.
9. A process for the preparation of a
3-(4,5-dihydroisoxazol-5-yl)benzoylc- yclohexenone of the formula I
as claimed in claim 1, which comprises acylating the cyclohexenone
of the formula II where R.sup.12.dbd.OH, where the variables
R.sup.13 to R.sup.18 have the meanings stated in claim 1, 189with
an activated carboxylic acid III.alpha. or with a carboxylic acid
III.beta., 190where the variables R.sup.1 to R.sup.7 have the
meanings stated in claim 1 and L.sup.1 is a nucleophilically
displaceable leaving group, and subjecting the acylation product to
a rearrangement reaction in the presence of a catalyst to give the
compounds I (where R.sup.12.dbd.OH) .
10. A process for the preparation of a
3-(4,5-dihydroisoxazol-5-yl)benzoyl- cyclohexenone of the formula I
where R.sup.12.dbd.OR.sup.19 or SR.sup.19 as claimed in claim 1, in
which a compound of the formula I where R.sup.12.dbd.OH or SH,
191where R.sup.1 to R.sup.7 and R.sup.13 to R.sup.18 have the
meaning stated in claim 1 is reacted with a compound of the formula
V L.sup.2-R.sup.19 V where the variable R.sup.19 has the meaning
stated in claim 1 and L.sup.2 is a nucleophilically displaceable
leaving group.
11. A process for the preparation of a
3-(4,5-dihydroisoxazol-5-yl)benzoyl- cyclohexenone of the formula I
where R.sup.12=halogen as claimed in claim 1, in which a compound
of the formula I where R.sup.12.dbd.OH, 192where the variables
R.sup.1 to R.sup.7 and R.sup.13 to R.sup.18 have the meaning stated
in claim 1 is reacted with a halogenating agent.
12. A process for the preparation of a
3-(4,5-dihydroisoxazol-5-yl)benzoyl- cyclohexenone of the formula I
where R.sup.12=mercapto, OR.sup.19 or SR.sup.19 as claimed in claim
1, in which a compound of the formula I where R.sup.12=halogen,
193where the variables R.sup.1 to R.sup.7 and R.sup.13 to R.sup.18
have the meaning stated in claim 1 is reacted with a compound of
the formula VI H.sub.2S or HOR.sup.19or HSR.sup.19 VI where
R.sup.19 has the meaning stated in claim 1, in the presence or
absence of a base.
13. A process for the preparation of a
3-(4,5-dihydroisoxazol-5-yl)benzoyl- cyclohexenone of the formula I
where R.sup.12.dbd.SOR.sup.20 or SO.sub.2R.sup.20 as claimed in
claim 1, in which a compound of the formula I where
R.sup.12.dbd.SR.sup.20, 194where the variables R.sup.1 to R.sup.7
and R.sup.13 to R.sup.18 have the meaning stated in claim 1, is
reacted with an oxidant.
14. A composition comprising a herbicidally active amount of at
least one 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I or of an agriculturally useful salt thereof as claimed in
claims 1 to 8 and adjuvants conventionally used for the formulation
of crop protection products.
15. A process for the preparation of a composition as claimed in
claim 14, which comprises mixing a herbicidally active amount of at
least one 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenone of the
formula I or of an agriculturally useful salt of I as claimed in
claims 1 to 8 and adjuvants conventionally used for the formulation
of crop protection products.
16. A method of controlling undesired vegetation, which comprises
allowing a herbicidally active amount of at least one
3-(4,5-dihydroisoxazol-5-yl)- benzoylcyclohexenone of the formula I
or of an agriculturally useful salt thereof as claimed in claims 1
to 8 to act on plants, their environment and/or on seeds.
17. The use of a 3-(4,5-dihydroisoxazol-3-yl)benzoylcyclohexenone
of the formula I and/or its agriculturally useful salts as claimed
in claims 1 to 8 as herbicide.
Description
[0001] The present invention relates to
3-(4,5-dihydroisoxazol-5-yl)benzoy- lcyclohexenones of the formula
I 1
[0002] in which the variables have the following meanings:
[0003] R.sup.1, R.sup.2 are hydrogen, nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl;
[0004] R .sup.3 is hydrogen, halogen or C.sub.1-C.sub.6-alkyl;
[0005] R.sup.4 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0006] R.sup.5, R.sup.6 are hydrogen, halogen, cyano, nitro,
C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkoxy) -C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1-C.sub.4-alkyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C- .sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0007] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0008] or
[0009] R.sup.5 and R.sup.6 together form a
C.sub.2-C.sub.6-alkanediyl chain which can be mono- to
tetrasubstituted by C.sub.1-C.sub.4-alkyl and/or can be interrupted
by oxygen or by unsubstituted or C.sub.1-C.sub.4-alkyl-substituted
nitrogen;
[0010] R.sup.7 is halogen, cyano, hydroxyl, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, amino,
C.sub.1-C.sub.6-alkylamino, di(C.sub.1-C.sub.6-alkyl)amino,
di(C.sub.1-C.sub.4-alkoxy)methyl,
hydroxylamino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-- C.sub.4-alkyl or
COR.sup.8;
[0011] R.sup.8 is hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalk- yl, hydroxyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub- .4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy or NR.sup.9R.sup.10;
[0012] R.sup.9 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0013] R.sup.10 is C.sub.1-C.sub.4-alkyl;
[0014] R.sup.11 is a cyclohexenone of the formula II 2
[0015] which is linked in the 2-position and where
[0016] R.sup.12 is hydroxyl, mercapto, halogen, OR.sup.19,
SR.sup.19, SOR.sup.20 or SO.sub.2R.sup.20;
[0017] R.sup.13, R.sup.17 are hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio or C.sub.1-C.sub.4-alkoxycarbonyl;
[0018] R.sup.14, R.sup.16, R.sup.18 are hydrogen or
C.sub.1-C.sub.4-alkyl;
[0019] R.sup.15 is hydrogen, hydroxyl, halogen,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
di(C.sub.1-C.sub.6-alkoxy)methyl, (C.sub.1-C.sub.6-alkoxy)
(C.sub.1-C.sub.6-alkylthio)methyl,
di(C.sub.1-C.sub.6-alkylthio)methyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-haloalkoxycarbonyl, 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, it being possible for the
six last-mentioned radicals to have attached to them one, two or
three substituents selected from amongst C.sub.1-C.sub.4-alkyl;
[0020] or
[0021] R.sup.13 and R.sup.14 or R.sup.17 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0022] R.sup.14 and R.sup.15 or R.sup.15 and R.sup.18 together are
a chemical bond or C.sub.1-C.sub.5-alkanediyl which can have
attached to it one, two or three substituents selected from amongst
halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0023] or
[0024] R.sup.14 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0025] or
[0026] R.sup.15 and R.sup.16 together are
--O--(CH.sub.2).sub.p--O--, --O--(CH.sub.2).sub.p--S--,
--S--(CH.sub.2).sub.p--S--, --O--(CH.sub.2).sub.q-- or
--S--(CH.sub.2).sub.q--, each of which can have attached to it one,
two or three substituents selected from amongst halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0027] or
[0028] R.sup.15 and R.sup.16 together are an oxygen atom;
[0029] R.sup.19 is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.20-alkylcarbonyl,
C.sub.2-C.sub.20-alkenylcarbonyl, C.sub.2-C.sub.6-alkynylcarbonyl,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.3-C.sub.6-alkenyloxycarbonyl,
C.sub.3-C.sub.6-alkynyloxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl,
C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl, N,
N-di(C.sub.1-C.sub.6-alkyl)amino- carbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarb-
onyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl-
,
N--(C.sub.1-C.sub.6-alkoxy)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl,
N,N-di(C.sub.1-C.sub.6-alkyl)aminothiocarbonyl,
C.sub.1-C.sub.6-alkoxyimi- no-C.sub.1-C.sub.6-alkyl, it being
possible for the abovementioned alkyl, alkoxy and cycloalkyl
radicals to be partially or fully halogenated and/or to have
attached to them one, two or three substituents selected from
amongst cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
di(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-al- koxycarbonyl,
C.sub.1-C.sub.4-alkylaminocarbonyl, N,N-di(C.sub.1-C.sub.4-a-
lkyl)aminocarbonyl or C.sub.3-C.sub.6-cycloalkyl; phenyl,
phenyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, heterocyclyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-- alkyl, heterocyclylcarbonyl,
heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, it being
possible for the phenyl or heterocyclyl radical of the
abovementioned radicals to be partially or fully halogenated and/or
to have attached to it one, two or three substituents selected from
amongst nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0030] R.sup.20 is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl or
C.sub.3-C.sub.6-cycloalkyl, it being possible for the
abovementioned alkyl and cycloalkyl radicals to be partially or
fully halogenated and/or to have attached to them one, two or three
substituents selected from amongst cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-al- koxycarbonyl,
C.sub.1-C.sub.4-alkylaminocarbonyl, N,N-di(C.sub.1-C.sub.4-a-
lkyl)aminocarbonyl or C.sub.3-C.sub.6-cycloalkyl; phenyl,
phenyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl, heterocyclyl-C.sub.1-C.sub.6-alkyl or
heterocyclylcarbonyl-C.sub.1-C.sub.6-alkyl, it being possible for
the phenyl or heterocyclyl radical of the abovementioned radicals
to be partially or fully halogenated and/or to have attached to it
one, two or three substituents selected from amongst nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy;
[0031] p is 2, 3 or 4;
[0032] q is 1, 2, 3, 4 or 5;
[0033] and to their agriculturally useful salts.
[0034] The invention furthermore relates to processes for the
preparation of compounds of the formula I, to compositions
comprising them, and to the use of these derivatives or
compositions comprising them for controlling harmful plants.
[0035] Benzoylcyclohexenones are disclosed in the literature, for
example in WO 96/26200.
[0036] However, the herbicidal properties of the prior-art
compounds and their tolerance by crop plants are only moderately
satisfactory.
[0037] It is an object of the present invention to find novel, in
particular herbicidally active, compounds with improved
properties.
[0038] We have found that this object is achieved by the
3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula I
and their herbicidal action.
[0039] Furthermore, there have been found herbicidal compositions
which comprise the compounds I and which have very good herbicidal
action. Moreover, there have been found processes for the
preparation of these compositions and methods of controlling
undesired vegetation using the compounds I.
[0040] Depending on the substitution pattern, the compounds of the
formula I may contain one or more chiral centers, in which case
they are present as enantiomer or diastereomer mixtures. The
invention relates both to the pure enantiomers or diastereomers and
to their mixtures.
[0041] The compounds of the formula I can also be present in the
form of their agriculturally useful salts, the type of the salt
generally being of no importance. Suitable are in general the salts
of those cations, or the acid addition salts of those acids, whose
cations, or anions, respectively, do not adversely affect the
herbicidal action of the compounds I.
[0042] 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, it being possible here, if desired, for one to four
hydrogen atoms to be replaced by C.sub.1-C.sub.4-alkyl or
hydroxy-C.sub.1-C.sub.4-alkyl and/or a phenyl or benzyl, preferably
ammonium, diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, and furthermore
phosphonium ions, sulfonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfonium and sulfoxonium ions,
preferably tri (C.sub.1-C.sub.4-alkyl)sulfoxonium.
[0043] Anions of useful acid addition salts are mainly chloride,
bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,
hydrogenphosphate, nitrate, hydrogencarbonate, carbonate,
hexafluorosilicate, hexafluorophosphate, benzoate, and the anions
of C.sub.1-C.sub.4-alkanoic acids, preferably formate, acetate,
propionate and butyrate.
[0044] The organic moieties stated for the substituents
R.sup.1-R.sup.20 or as radicals on phenyl rings constitute
collective terms for individual enumerations of the individual
group members. All hydrocarbon chains, that is to say all alkyl,
haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio,
haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,
haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl,
alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl,
haloalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,
alkylthiocarbonyl, alkylaminocarbonyl, alkenylaminocarbonyl,
alkynylaminocarbonyl, dialkylaminocarbonyl, (alkenyl)
(alkyl)aminocarbonyl, (alkynyl)(alkyl)aminocarbonyl,
N-alkoxy-N-alkylaminocarbonyl, N,N-dialkylaminothiocarbonyl,
alkoxyalkoxycarbonyl, alkenyloxy, alkynyloxy, alkylamino,
dialkylamino, alkoxyalkyl, dialkoxymethyl,
(alkoxy)(alkylthio)methyl, dialkoxyalkyl, alkylthioalkyl,
di(alkylthio)methyl, dialkylaminoalkyl, dialkylaminoiminoalkyl,
hydroxyiminoalkyl, alkoxyiminoalkyl, alkoxycarbonylalkyl,
alkoxyalkoxy, alkenyl, haloalkenyl, alkenyloxy, alkynyl and
alkynyloxy moieties and the hydrocarbon chains of phenylalkyl,
phenylcarbonylalkyl, heterocyclylalkyl and
heterocyclylcarbonylalkyl, C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenylcarbonyl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl and
heterocyclylcarbonyl-C.sub.1-C.sub.4-alkyl can be straight-chain or
branched. Unless otherwise specified, halogenated substituents
preferably have attached to them one to five identical or different
halogen atoms. The meaning halogen is in each case fluorine,
chlorine, bromine or iodine.
[0045] Other examples of meanings are:
[0046] C.sub.1-C.sub.4-alkyl and the alkyl moieties of
C.sub.1-C.sub.4-alkylcarbonyl,
di(C.sub.1-C.sub.4-alkoxy)-C.sub.1-C.sub.4- -alkyl,
di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylaminocarbonyl,
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenylcarbonyl-C.sub.1-C.sub.4-alkyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl and
heterocyclylcarbonyl-C.sub.1-C.sub.4-alkyl: for example methyl,
ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl
and 1,1-dimethylethyl;
[0047] C.sub.1-C.sub.6-alkyl and the alkyl moieties of
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl,
N--C.sub.3-C.sub.6-alkenyl-N--C.sub.1-C.sub.6-alkylaminocarbonyl,
N--C.sub.1-C.sub.6-alkynyl-N--C.sub.1-C.sub.6-alkylaminocarbonyl,
N--C.sub.1-C.sub.6-alkoxy-N--C.sub.1-C.sub.6-alkylaminocarbonyl,
phenyl-C.sub.1-C.sub.6-alkyl, phenylcarbonyl-C.sub.1-C.sub.6-alkyl,
heterocyclyl-C.sub.1-C.sub.6-alkyl and
heterocyclylcarbonyl-C.sub.1-C.sub- .6-alkyl: C.sub.1-C.sub.4-alkyl
as mentioned above and, 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, 2-ethylbutyl,
1,1,2-trimethylpropyl, 1-ethyl-l-methylpropyl and
1-ethyl-3-methylpropyl;
[0048] C.sub.1-C.sub.20-alkyl as alkyl moiety of
C.sub.1-C.sub.20-alkylcar- bonyl: C.sub.1-C.sub.6-alkyl as
mentioned above and heptyl, octyl, pentadecyl or heptadecyl;
[0049] C.sub.1-C.sub.4-haloalkyl and the haloalkyl moieties of
C.sub.1-C.sub.4-haloalkylcarbonyl: a C.sub.1-C.sub.4-alkyl radical
as mentioned above which is partially or fully substituted by
fluorine, chlorine, bromine and/or iodine, i.e. e.g. chloromethyl,
dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,
trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,
chlorodifluoromethyl, bromoethyl, iodomethyl, 1-fluoroethyl,
1-chloroethyl, 1-bromoethyl, 1-iodoethyl, 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 and nonafluorobutyl;
[0050] C.sub.1-C.sub.6-haloalkyl: C.sub.1-C.sub.4-haloalkyl as
mentioned above and, for example, 5-fluoropentyl, 5-chloropentyl,
5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,
6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;
[0051] C.sub.1-C.sub.4-cyanoalkyl: for example cyanomethyl,
1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl,
2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl,
2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl,
3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,
1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,
2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and
2-cyanomethylprop-2-yl;
[0052] C.sub.3-C.sub.6-alkenyl and the alkenyl moieties of
C.sub.3-C.sub.6-alkenylcarbonyl,
C.sub.3-C.sub.6-alkenylaminocarbonyl,
N--(C.sub.3-C.sub.6-alkenyl)-N--(C.sub.1-C.sub.6-alkyl)aminocarbonyl:
prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl,
buten-2-yl, buten-3-yl, 1-methylprop-l-en-1-yl,
2-methylprop-l-en-1-yl, 1-methylprop-2-en-1-yl,
2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl,
penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-l-en-1-yl,
3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl,
2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,
1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,
3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,
1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,
1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-l-en-1-yl,
hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,
1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl,
3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,
1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,
3-methylpent-2-en-1-yl, 4-methylpent-2-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-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,
1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,
1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,
2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,
2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,
3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,
1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,
2-ethylbut-l-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,
1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-l-methylprop-2-en-1-yl,
1-ethyl-2-methylprop-1-en-1-yl and
1-ethyl-2-methylprop-2-en-1-yl;
[0053] C.sub.2-C.sub.6-alkenyl as alkenyl moieties of
C.sub.2-C.sub.6-alkenylcarbonyl: C.sub.3-C.sub.6-alkenyl as
mentioned above, and also ethenyl;
[0054] C.sub.2-C.sub.20-alkenyl as alkenyl moieties of
C.sub.2-C.sub.20-alkenylcarbonyl: C.sub.2-C.sub.6-alkenyl as
mentioned above, and also 8-pentadecen-1-yl, 8-heptadecen-1-yl and
8,11-heptadecadien-1-yl;
[0055] C.sub.3-C.sub.6-haloalkenyl: a C.sub.3-C.sub.6-alkenyl
radical as mentioned above which is partially or fully substituted
by fluorine, chlorine, bromine and/or iodine, i.e. for example
2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,
2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl,
3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,
2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
[0056] C.sub.3-C.sub.6-alkynyl and the alkynyl moieties of
C.sub.3-C.sub.6-alkynylcarbonyl,
C.sub.3-C.sub.6-alkynylaminocarbonyl,
N--(C.sub.3-C.sub.6-alkynyl)-N--(C.sub.1-C.sub.6-alkyl)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;
[0057] C.sub.2-C.sub.6-alkynyl as alkynyl moiety of
C.sub.2-C.sub.6-alkynylcarbonyl: C.sub.3-C.sub.6-alkynyl as
mentioned above, and also ethynyl;
[0058] C.sub.1-C.sub.4-alkoxy and the alkoxy moieties of
di(C.sub.1-C.sub.4-alkoxy)methyl and
di(C.sub.1-C.sub.4-alkoxy)-C.sub.1-C- .sub.4-alkyl: for example
methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,
2-methylpropoxy and 1,1-dimethylethoxy;
[0059] C.sub.1-C.sub.6-alkoxy and the alkoxy moieties of
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino C.sub.1-C.sub.6-alkyl,
N--C.sub.1-C.sub.6-alkoxy-N--C.sub.1-C.sub.6-alkylaminocarbonyl,
di(C.sub.1-C.sub.6-alkoxy)methyl and (C.sub.1-C.sub.6-alkoxy)
(C.sub.1-C.sub.6-alkylthio)methyl: C.sub.1-C.sub.4-alkoxy as
mentioned above, and also for example pentoxy, 1-methylbutoxy,
2-methylbutoxy, 3-methoxylbutoxy, 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,
1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,
1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and
1-ethyl-2-methylpropoxy;
[0060] C.sub.1-C.sub.4-haloalkoxy: a C.sub.1-C.sub.4-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-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,
3-fluoropropoxy, 2-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-fluo- roethoxy,
1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,
4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and
nonafluorobutoxy;
[0061] C.sub.1-C.sub.6-haloalkoxy: C.sub.1-C.sub.4-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 and dodecafluorohexoxy;
[0062] C.sub.1-C.sub.4-alkylthio: for example methylthio,
ethylthio, propylthio, 1-methylethylthio, butylthio,
1-methylpropylthio, 2-methylpropylthio and
1,1-dimethylethylthio;
[0063] C.sub.1-C.sub.6-alkylthio and the alkylthio moieties of
(C.sub.1-C.sub.6-alkoxy) (C.sub.1-C.sub.6-alkylthio)methyl,
di(C.sub.1-C.sub.6-alkylthio)methyl and
C.sub.1-C.sub.6-alkylthiocarbonyl- : C.sub.1-C.sub.4-alkylthio as
mentioned above, and also for example pentylthio,
1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,
2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,
1,1-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, 1,1,2-trimethylpropylthio,
1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and
1-ethyl-2-methylpropylthio;
[0064] C.sub.1-C.sub.4-haloalkylthio: a C.sub.1-C.sub.4-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-bromoethylthio, 4-fluorobutylthio,
4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;
[0065] C.sub.1-C.sub.6-haloalkylthio: C.sub.1-C.sub.4-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 and dodecafluorohexylthio;
[0066] C.sub.1-C.sub.6-alkylsulfinyl
(C.sub.1-C.sub.6-alkyl-S(.dbd.O)--): for example methylsulfinyl,
ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl,
butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1,1-dimethylethylsulfinyl, 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,
1-ethyl-1-methylpropylsulfinyl and
1-ethyl-2-methylpropylsulfinyl;
[0067] C.sub.1-C.sub.6-haloalkylsulfinyl:
C.sub.1-C.sub.6-alkylsulfinyl radical 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-trifluoroethylsulfi- nyl, 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,
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-chloroethylsul- finyl,
1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,
4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,
nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,
5-chloropentylsulfinyl, 5-bromopentylsulfinyl,
5-iodopentylsulfinyl, undecafluoropentylsulfinyl,
6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,
6-iodohexylsulfinyl and dodecafluorohexylsulfinyl;
[0068] C.sub.1-C.sub.4-alkylsulfonyl
(C.sub.1-C.sub.6-alkyl-S(.dbd.O).sub.- 2--) : for example
methylsulfonyl, ethylsulfonyl, propylsulfonyl,
1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,
2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;
[0069] C.sub.1-C.sub.6-alkylsulfonyl: C.sub.1-C.sub.4-alkylsulfonyl
as mentioned above, and also for example pentylsulfonyl,
1-methylbutylsulfonyl, 2-methylbutylsulfonyl,
3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,
1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,
1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,
2-methylpentylsulfonyl, 3-methylpentylsulfonyl,
4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,
1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,
2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,
3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,
2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,
1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and
1-ethyl-2-methylpropylsulfonyl;
[0070] C.sub.1-C.sub.4-haloalkylsulfonyl: a
C.sub.1-C.sub.6-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-trifluoroethylsulfo- nyl, 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-chloroethylsul- fonyl,
1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,
4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and
nonafluorobutylsulfonyl;
[0071] C.sub.1-C.sub.6-haloalkylsulfonyl: a
C.sub.1-C.sub.4-haloalkylsulfo- nyl radical as mentioned above, and
also 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl,
5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,
6-bromohexylsulfonyl, 6-iodohexylsulfonyl and
dodecafluorohexylsulfonyl;
[0072] C.sub.1-C.sub.4-alkoxycarbonyl: for example methoxycarbonyl,
ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl,
butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl
and 1,1-dimethoxycarbonyl;
[0073] C.sub.1-C.sub.6-alkoxycarbonyl: a
C.sub.1-C.sub.4-alkoxycarbonyl radical as mentioned above, and also
for example: pentoxycarbonyl, 1-methylbutoxycarbonyl,
2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,
1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,
2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl,
hexoxycarbonyl, 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,
1,2,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,
1-ethyl-1-methylpropoxycarbonyl and
1-ethyl-2-methylpropoxycarbonyl;
[0074] C.sub.1-C.sub.4-haloalkoxycarbonyl: a
C.sub.1-C.sub.4-alkoxycarbony- l 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-trifluoroethoxyca- rbonyl,
2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbon-
yl, 2,2-dichloro-2-fluoroethoxycarbonyl,
2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl,
2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl,
2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl- ,
2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,
2,2-difluoropropoxycarbo- nyl, 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-chloroethoxyc- arbonyl,
1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,
4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl and
4-iodobutoxycarbonyl;
[0075] C.sub.1-C.sub.6-haloalkoxycarbonyl: a
C.sub.1-C.sub.4-haloalkoxycar- bonyl radical as mentioned above,
and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl,
5-bromopentoxycarbonyl, 5-iodopentoxycarbonyl,
6-fluorohexoxycarbonyl, 6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl
and dodecafluorohexoxycarbonyl;
[0076] C.sub.3-C.sub.6-alkenyloxy and the
C.sub.3-C.sub.6-alkenyloxy moieties of
C.sub.3-C.sub.6-Alkenyloxycarbonyl: for example prop-1-en-1-yloxy,
prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy,
buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy,
2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy,
2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy,
penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy,
2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy,
1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy,
3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy,
2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy,
1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy,
1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy,
1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy,
hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy,
1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3
-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,
1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,
3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,
1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,
3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,
1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,
3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,
1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,
1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,
1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy,
1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,
2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy,
2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,
3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,
1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,
1-ethylbut-3-en-1-yloxy- , 2-ethylbut-1-en-1-yloxy,
2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,
1,1,2-trimethylprop-2-en-1-yloxy,
1-ethyl-1-methylprop-2-en-1-yloxy,
1-ethyl-2-methylprop-1-en-1-yloxy and
1-ethyl-2-methylprop-2-en-1-yloxy;
[0077] C.sub.3-C.sub.6-alkynyloxy and the alkynyloxy moieties of
C.sub.3-C.sub.6-alkynyloxycarbonyl: for example prop-1-yn-1-yloxy,
prop-2-yn-1-yloxy, but-1-yn-1-yloxy, but-1-yn-3-yloxy,
but-1-yn-4-yloxy, but-2-yn-1-yloxy, pent-1-yn-1-yloxy,
pent-1-yn-3-yloxy, pent-1-yn-4-yloxy, pent-1-yn-5-yloxy,
pent-2-yn-1-yloxy, pent-2-yn-4-yloxy, pent-2-yn-5-yloxy,
3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy,
hex-1-yn-1-yloxy, hex-1-yn-3-yloxy, hex-1-yn-4-yloxy,
hex-1-yn-5-yloxy, hex-1-yn-6-yloxy, hex-2-yn-1-yloxy,
hex-2-yn-4-yloxy, hex-2-yn-5-yloxy, hex-2-yn-6-yloxy,
hex-3-yn-1-yloxy, hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy,
3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy,
3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy,
4-methylpent-2-yn-4-yloxy and 4-methylpent-2-yn-5-yloxy;
[0078] C.sub.1-C.sub.6-alkylamino and the alkylamino moieties of
C.sub.1-C.sub.6-alkylaminocarbonyl: for example methylamino,
ethylamino, propylamino, 1-methylethylamino, butylamino,
1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino,
pentylamino, 1-methylbutylamino, 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;
[0079] di(C.sub.1-C.sub.4-alkyl)amino and the dialkylamino moieties
of di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1-C.sub.4-alkyl and
di(C.sub.1-C.sub.4-alkyl)aminocarbonyl: 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)amin- o,
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-methylp- ropyl)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 and
N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
[0080] di(C.sub.1-C.sub.6-alkyl)amino and the dialkylamino moieties
of di(C.sub.1-C.sub.6-alkyl)aminocarbonyl and
di(C.sub.1-C.sub.6-alkyl)amino- thiocarbonyl:
di(C.sub.1-C.sub.4-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;
[0081] di(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkyl:
C.sub.1-C.sub.4-alkyl substituted by di(C.sub.1-C.sub.4-alkyl)amino
as mentioned above, i.e., for example, N,N-dimethylaminomethyl,
N,N-diethylaminomethyl, N,N-dipropylaminomethyl,
N,N-di(1-methylethyl)ami- nomethyl, N,N-dibutylaminomethyl,
N,N-di(1-methylpropyl)aminomethyl,
N,N-di(2-methylpropyl)aminomethyl,
N,N-di(1,1-dimethylethyl)aminomethyl, N-ethyl-N-methylaminomethyl,
N-methyl-N-propylaminomethyl,
N-methyl-N-(1-methylethyl)aminomethyl, N-butyl-N-methylaminomethyl,
N-methyl-N-(1-methylpropyl)aminomethyl,
N-methyl-N-(2-methylpropyl)aminom- ethyl,
N-(1,1-dimethylethyl)-N-methylaminomethyl,
N-ethyl-N-propylaminomet- hyl,
N-ethyl-N-(1-methylethyl)aminomethyl, N-butyl-N-ethylaminomethyl,
N-ethyl-N-(1-methylpropyl)aminomethyl,
N-ethyl-N-(2-methylpropyl)aminomet- hyl,
N-ethyl-N-(1,1-dimethylethyl)aminomethyl,
N-(1-methylethyl)-N-propyla- minomethyl,
N-butyl-N-propylaminomethyl, N-(1-methylpropyl)-N-propylaminom-
ethyl, N-(2-methylpropyl)-N-propylaminomethyl,
N-(1,1-dimethylethyl)-N-pro- pylaminomethyl,
N-butyl-N-(1-methylethyl)aminomethyl,
N-(1-methylethyl)-N-(1-methylpropyl)aminomethyl,
N-(1-methylethyl)-N-(2-m- ethylpropyl)aminomethyl,
N-(1,1-dimethylethyl)-N-(1-methylethyl)aminomethy- l,
N-butyl-N-(1-methylpropyl)aminomethyl,
N-butyl-N-(2-methylpropyl)aminom- ethyl,
N-butyl-N-(1,1-dimethylethyl)aminomethyl,
N-(1-methylpropyl)-N-(2-m- ethylpropyl)aminomethyl,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminometh- yl,
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminomethyl,
2-(N,N-dimethylamino)ethyl, 2-(N,N-diethylamino)ethyl,
2-(N,N-dipropylamino)ethyl, 2-[N,N-di-(1-methylethyl)amino]ethyl,
2-[N,N-dibutylamino]ethyl, 2-[N,N-di(1-methylpropyl)amino]ethyl,
2-[N,N-di(2-methylpropyl)amino]ethyl,
2-[N,N-di(1,l-dimethylethyl)amino]e- thyl,
2-[N-ethyl-N-methylamino]ethyl, 2-[N-methyl-N-propylamino]ethyl,
2-[N-methyl-N-(1-methylethyl)amino]ethyl,
2-[N-butyl-N-methylamino]ethyl,
2-[N-methyl-N-(1-methylpropyl)amino]ethyl,
2-[N-methyl-N-(2-methylpropyl)- amino]ethyl,
2-[N-(1,1-dimethylethyl)-N-methylamino]ethyl,
2-[N-ethyl-N-propylamino]ethyl,
2-[N-ethyl-N-(1-methylethyl)amino]ethyl,
2-[N-butyl-N-ethylamino]ethyl,
2-[N-ethyl-N-(1-methylpropyl)amino]ethyl,
2-[N-ethyl-N-(2-methylpropyl)amino]ethyl,
2-[N-ethyl-N-(1,1-dimethylethyl- amino]ethyl,
2-[N-(1-methylethyl)-N-propylamino]ethyl,
2-[N-Butyl-N-propylamino]ethyl,
2-[N-(1-methylpropyl)-N-propylamino]ethyl- ,
2-[N-(2-methylpropyl)-N-propylamino]ethyl,
2-[N-(1,1-dimethylethyl)-N-pr- opylamino]ethyl,
2-[N-butyl-N-(1-methylethyl)amino]ethyl,
2-[N-(1-methylethyl)-N-(1-methylpropyl)amino]ethyl,
2-[N-(1-methylethyl)-N-(2-methylpropyl)amino]ethyl, 2-[N-(1,
1-dimethylethyl) -N-(1-methylethyl)amino]ethyl,
2-[N-butyl-N-(1-methylpro- pyl)amino]ethyl,
2-[N-butyl-N-(2-methylpropyl)amino]ethyl,
2-[N-butyl-N-(1,1-dimethylethyl)amino]ethyl,
2-[N-(1-methylpropyl)-N-(2-m- ethylpropyl)amino]ethyl,
2-[N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino]- ethyl,
2-[N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino]ethyl,
3-(N,N-dimethylamino)propyl, 3-(N,N-diethylamino)propyl,
4-(N,N-dimethylamino)butyl and 4-(N,N-diethylamino)butyl;
[0082] C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl:
C.sub.1-C.sub.4-alkyl substituted by C.sub.1-C.sub.4-alkoxy as
mentioned above, i.e., for example, methoxymethyl, ethoxymethyl,
propoxymethyl, (1-methylethoxy)methyl, butoxymethyl,
(1-methylpropoxy)methyl, (2-methylpropoxy)methyl,
(1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,
2-(Propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy) ethyl,
2-(1-methylpropoxy) ethyl, 2-(2-methylpropoxy)ethyl,
2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl,
2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,
2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,
2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl,
3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl,
3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,
3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,
2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,
2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,
2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,
3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,
3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,
3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,
4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,
4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and
4-(1,1-dimethylethoxy)butyl;
[0083] C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl:
C.sub.1-C.sub.4-alkyl substituted by C.sub.1-C.sub.4-alkylthio as
mentioned above, i.e., for example, methylthiomethyl,
ethylthiomethyl, propylthiomethyl, (1-methylethylthio)methyl,
butylthiomethyl, (1-methylpropylthio)methyl,
(2-methylpropylthio)methyl, (1,1-dimethylethylthio)methyl,
2-methylthioethyl, 2-ethylthioethyl, 2-(propylthio)ethyl,
2-(1-methylethylthio)ethyl, 2-(butylthio)ethyl,
2-(1-methylpropylthio) ethyl, 2-(2-methylpropylthio)ethyl,
2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl,
3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl,
3-(propylthio)propyl, 3-(butylthio)propyl, 4-(methylthio)butyl,
4-(ethylthio)butyl, 4-(propylthio)butyl and 4-(butylthio)butyl;
[0084] C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl:
C.sub.1-C.sub.4-alkyl substituted by
C.sub.1-C.sub.4-alkoxycarbonyl, i.e., for example,
methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl,
(1-methylethoxycarbonyl)methyl, butoxycarbonylmethyl,
(1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl,
(1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl,
2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,
2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl,
2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)ethyl,
2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl,
2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl,
2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl,
2-(1-methylpropoxycarbonyl)propyl,
2-(2-methylpropoxycarbonyl)propyl,
2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl,
3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl,
3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl,
3-(1-methylpropoxycarbonyl)propyl,
3-(2-methylpropoxycarbonyl)propyl,
3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl,
2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl,
2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl,
2-(1-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)butyl,
2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl,
3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl,
3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl,
3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl,
3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl,
4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl,
4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl,
4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and
4-(1,1-dimethylethoxycarbonyl)butyl;
[0085] C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy:
C.sub.2-C.sub.4-alkoxy substituted by C.sub.1-C.sub.4-alkoxy as
mentioned above, i.e., for example, 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-(i-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 and
4-(1,1-dimethylethoxy)butoxy;
[0086] C.sub.2-C.sub.5-alkanediyl: for example ethane-1,2-diyl,
propane-1,3-diyl, butane-1,4-diyl and pentane-1,5-diyl;
[0087] C.sub.1-C.sub.5-alkanediyl: C.sub.2-C.sub.5-alkanediyl as
mentioned above, and also methanediyl;
[0088] C.sub.2-C.sub.6-alkanediyl: C.sub.2-C.sub.5-alkanediyl as
mentioned above, and also hexane-1,6-diyl;
[0089] C.sub.3-C.sub.6-cycloalkyl: for example cyclopropyl,
cyclobutyl, cyclopentyl and cyclohexyl;
[0090] C.sub.3-C.sub.8-cycloalkyl: C.sub.3-C.sub.6-cycloalkyl as
mentioned above, and also cycloheptyl and cyclooctyl;
[0091] heterocyclyl and heterocyclyl moieties of
heterocyclylcarbonyl, heterocyclyl-C.sub.1-C.sub.6-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.6-- alkyl: a saturated,
partially saturated or unsaturated 5- or 6-membered heterocyclic
ring which contains one to four identical or different hetero atoms
selected from the following group: oxygen, sulfur or nitrogen,
i.e., for example, 5-membered saturated rings such as:
[0092] tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,
tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl,
tetrahydropyrrol-3-yl, 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,
1,3,2-dioxathiolan-4-yl;
[0093] 5-membered partially saturated rings such as:
[0094] 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,
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,
.DELTA..sup.3-1,2-dithiol-3-yl, .DELTA..sup.3-1,2-dithiol-4-yl,
.DELTA..sup.3-1,2-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-oxathiol-4-yl, 1,3-oxathiol-5-yl,
1,2,3-.DELTA..sup.2-oxadiazolin-4-yl,
1,2,3-.DELTA..sup.2-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.4-oxadiazolin-3-y- l,
1,2,4-.DELTA..sup.4-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.2-oxadiazolin-3- -yl,
1,2,4-.DELTA..sup.2-oxadiazolin-5-yl,
1,2,4-.DELTA..sup.3-oxadiazolin- -3-yl,
1,2,4-.DELTA..sup.3-oxadiazolin-5-yl,
1,3,4-.DELTA..sup.2-oxadiazol- in-2-yl,
1,3,4-.DELTA..sup.2-oxadiazolin-5-yl, 1,3,4-.DELTA..sup.3-oxadiaz-
olin-2-yl, 1,3,4-oxadiazolin-2-yl,
1,2,4-.DELTA..sup.4-thiadiazolin-3-yl,
1,2,4-.DELTA..sup.4-thiadiazolin-5-yl,
1,2,4-.DELTA..sup.3-thiadiazolin-3- -yl,
1,2,4-.DELTA..sup.3-thiadiazolin-5-yl,
1,2,4-.DELTA..sup.2-thiadiazol- in-3-yl,
1,2,4-.DELTA..sup.2-thiadiazolin-5-yl, 1,3,4-.DELTA..sup.2-thiadi-
azolin-2-yl, 1,3,4-.DELTA..sup.2-thiadiazolin-5-yl,
1,3,4-.DELTA..sup.3-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,
1,2,3-.DELTA..sup.2-triazolin-4-yl,
1,2,3-.DELTA..sup.2-triazolin-5-yl,
1,2,4-.DELTA..sup.2-triazolin-3-yl,
1,2,4-.DELTA..sup.2-triazolin-5-yl,
1,2,4-.DELTA..sup.3-triazolin-3-yl,
1,2,4-.DELTA..sup.3-triazolin-5-yl,
1,2,4-.DELTA..sup.1-triazolin-2-yl, 1,2,4-triazolin-3-yl,
3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl,
2H-1,3,4-oxathiazol-5-y- l;
[0095] 5-membered, unsaturated rings such as:
[0096] 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl,
pyrrol-3-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, thiazol-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, 1,2,4-thiadiazol-3-yl,
1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl,
1,2,4-triazol-3-yl, tetrazol-5-yl;
[0097] 6-membered saturated rings such as:
[0098] tetrahydropyran-2-yl, tetrahydropyran-3-yl,
tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl,
piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,
tetrahydrothiopyran-4-yl, 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-1,2-oxazin-3-yl,
tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl,
tetrahydro-1,2-oxazin-6-yl;
[0099] 6-membered partially saturated rings such as:
[0100] 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, 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;
[0101] 6-membered unsaturated rings such as:
[0102] pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl,
pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl,
pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl,
1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,4,5-tetrazin-3-yl;
[0103] it optionally being possible for the sulfur of the
abovementioned heterocycles to be oxidized to S.dbd.O or
S(.dbd.O).sub.2
[0104] and it being possible for a bicyclic ring system to be
formed with a fused phenyl ring or with a
C.sub.3-C.sub.6-carbocycle or with a further 5- to 6-membered
heterocycle.
[0105] The following heterocyclyl radicals are preferably used:
[0106] 5-membered unsaturated rings as mentioned above, in
particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl,
pyrrol-3-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl,
isoxazol-4-yl, isoxazol-5-yl, imidazol-2-yl, imidazol-4-yl,
oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl,
thiazol-5-yl or 1,2,4-triazol-3-yl;
[0107] 6-membered unsaturated rings as mentioned above, in
particular pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,
pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl or
1,3,5-triazin-2-yl;
[0108] all phenyl or heterocyclyl rings are preferably
unsubstituted or have attached to them one to three halogen atoms
and/or one nitro group, one cyano radical and/or one or two methyl,
trifluoromethyl, methoxy or trifluoromethoxy substituents.
[0109] In view of 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 alone or in
combination:
[0110] R.sup.1, R.sup.2 are nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl;
[0111] especially preferably nitro, halogen such as, for example,
chlorine and bromine, C.sub.1-C.sub.6-alkyl such as, for example,
methyl and ethyl, C.sub.1-C.sub.6-alkoxy such as, for example,
methoxy and ethoxy, C.sub.1-C.sub.6-haloalkyl such as, for example,
difluoromethyl and trifluoromethyl, C.sub.1-C.sub.6-alkylthio such
as, for example, methylthio and ethylthio,
C.sub.1-C.sub.6-alkylsulfinyl such as, for example, methylsulfinyl
and ethylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl such as, for
example, methylsulfonyl, ethylsulfonyl and propylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl such as, for example,
trifluoromethylsulfonyl and pentafluoroethylsulfonyl;
[0112] R.sup.3 is hydrogen;
[0113] R.sup.4 is hydrogen;
[0114] R.sup.5, R.sup.6 are hydrogen, halogen, cyano, nitro,
C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0115] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0116] or
[0117] R.sup.5 and R.sup.6 together form a
C.sub.2-C.sub.6-alkanediyl chain which can be mono- to
tetrasubstituted by C.sub.1-C.sub.4-alkyl and/or can be interrupted
by oxygen or an unsubstituted or C.sub.1-C.sub.4-alkyl-substituted
nitrogen;
[0118] R.sup.5 is especially preferably hydrogen, halogen, cyano,
nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0119] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0120] R.sup.6 is especially preferably hydrogen or
C.sub.1-C.sub.4-alkyl; particularly preferably R.sup.5 is hydrogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxycarbonyl or CONR.sup.9R.sup.10;
[0121] particularly preferably R.sup.6 is hydrogen or
C.sub.1-C.sub.4-alkyl; very especially preferably R.sup.5 is
hydrogen or C.sub.1-C.sub.4-alkyl, particularly hydrogen;
[0122] very especially preferably R.sup.6 is hydrogen;
[0123] R.sup.7 is halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalky- l, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, amino, C.sub.1-C.sub.6-alkylamino,
di(C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.4-alkoxy)methyl or
COR.sup.8;
[0124] especially preferably C.sub.1-C.sub.4-alkyl such as, for
example, methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,
C.sub.1-C.sub.4-alkylcarbonyl such as, for example, methylcarbonyl
or ethylcarbonyl, hydroxycarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl
such as, for example, methoxycarbonyl or ethoxycarbonyl;
[0125] particularly preferably C.sub.1-C.sub.4-alkyl such as, for
example, methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,
hydroxycarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl;
[0126] very especially preferably C.sub.1-C.sub.4-alkyl such as,
for example, methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl;
[0127] R.sup.8 is C.sub.1-C.sub.4-alkyl, hydroxyl,
C.sub.1-C.sub.4-alkoxy or NR.sup.9R.sup.10;
[0128] R.sup.9 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0129] R.sup.10 is C.sub.1-C.sub.4-alkyl;
[0130] R.sup.12 is hydroxyl, OR.sup.19, SR.sup.19, SOR.sup.20 or
SO.sub.2R.sup.20;
[0131] particularly hydroxyl, OR.sup.19 or SR.sup.19;
[0132] especially preferably hydroxyl;
[0133] R.sup.13, R.sup.17 are hydrogen, C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkylthio;
[0134] particularly hydrogen, methyl or methylthio;
[0135] especially preferably hydrogen or methyl, particularly
preferably hydrogen;
[0136] R.sup.14, R.sup.16, R.sup.18 are hydrogen or methyl;
[0137] R.sup.15 is hydrogen, hydroxyl, C.sub.1-C.sub.6-alkyl or
di(C.sub.1-C.sub.6-alkoxy)methyl;
[0138] particularly hydrogen or C.sub.1-C.sub.4-alkyl;
[0139] or
[0140] R.sup.13 and R.sup.14 or R.sup.14 and R.sup.15 or R.sup.15
and R.sup.18 or R.sup.14 and R.sup.18 or R.sup.17 and R.sup.18
together are C.sub.1-C.sub.5-alkanediyl which can have attached to
it one, two or three substituents selected from among halogen,
cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0141] or
[0142] R.sup.15 and R.sup.16 together are an oxygen atom;
[0143] R.sup.19 is C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.20-alkylcarbonyl, preferably
C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl, it being possible for the
abovementioned alkyl and alkoxy radicals to be partially or fully
halogenated and/or to have attached to them one, two or three
substituents selected from among cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl or C.sub.3-C.sub.6-cycloalkyl;
[0144] phenyl, phenyl-C.sub.1-C.sub.4-alkyl,
phenylcarbonyl-C.sub.1-C.sub.- 4-alkyl, phenylcarbonyl,
phenoxycarbonyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.4-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.4-- alkyl,
heterocyclyloxycarbonyl, it being possible for the phenyl or
heterocyclyl radical of the abovementioned radicals to be partially
or fully halogenated and/or to have attached to it one, two or
three substituents selected from among nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy;
[0145] R.sup.20 is C.sub.1-C.sub.6-alkyl which can be partially or
fully halogenated and/or can have attached to it one, two or three
substituents selected from among cyano, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl or C.sub.3-C.sub.6-cycloalkyl;
phenyl, phenyl-C.sub.1-C.sub.4-alkyl,
phenylcarbonyl-C.sub.1-C.sub.4-alkyl, heterocyclyl,
heterocyclyl-C.sub.1-C.sub.4-alkyl or
heterocyclylcarbonyl-C.sub.1-C.sub.4-alkyl, it being possible for
the phenyl or heterocyclyl radical of the abovementioned radicals
to be partially or fully halogenated and/or to have attached to it
one, two or three substituents selected from among nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy.
[0146] The following embodiments of the
3-(4,5-dihydroisoxazol-5-yl)benzoy- lcyclohexenones of the formula
I must be emphasized:
[0147] 1. In a preferred embodiment of the
3-(4,5-dihydroisoxazol-5-yl)ben- zoylcyclohexenones of the formula
I,
[0148] R.sup.1 is nitro, halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-haloalkoxy;
[0149] especially preferably nitro, halogen such as chlorine or
bromine, C.sub.1-C.sub.4-alkyl such as methyl or ethyl,
C.sub.1-C.sub.4-haloalkyl such as difluoromethyl or
trifluoromethyl, C.sub.1-C.sub.4-alkoxy such as methoxy or ethoxy,
or C.sub.1-C.sub.4-haloalkoxy such as difluoromethoxy or
trifluoromethoxy;
[0150] particularly preferably halogen such as chlorine or bromine,
C.sub.1-C.sub.4-alkyl such as methyl or ethyl or
C.sub.1-C.sub.4-alkoxy such as methoxy or ethoxy;
[0151] very especially preferably halogen, such as chlorine or
bromine or C.sub.1-C.sub.4-alkyl such as methyl or ethyl;
[0152] R.sup.2 is halogen, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl;
[0153] especially preferably halogen such as fluorine or chlorine,
C.sub.1-C.sub.4-haloalkyl such as difluoromethyl or
trifluoromethyl, or C.sub.1-C.sub.4-alkylsulfonyl such as
methylsulfonyl or ethylsulfonyl;
[0154] particularly preferably halogen such as fluorine or
chlorine, or C.sub.1-C.sub.4-alkylsulfonyl such as methylsulfonyl
or ethylsulfonyl;
[0155] very especially preferably C.sub.1-C.sub.4-alkylsulfonyl
such as methylsulfonyl or ethylsulfonyl;
[0156] 2. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I,
[0157] R.sup.3 is hydrogen.
[0158] 3. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I,
[0159] R.sup.3 is halogen or C.sub.1-C.sub.4-alkyl;
[0160] particularly preferably chlorine or methyl.
[0161] 4. In a further embodiment of the
3-(4,5-dihydroisoxazol-5-yl)benzo- ylcyclohexenones of the formula
I,
[0162] R.sup.4 is hydrogen.
[0163] 5. In a further embodiment of the
3-(4,5-dihydroisoxazol-5-yl)benzo- ylcyclohexenones of the formula
I,
[0164] R.sup.4 is hydrogen;
[0165] R.sup.5 is hydrogen, halogen, cyano, nitro,
C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbo- nyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl- ,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy- , C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl,
CONR.sup.9R.sup.10, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0166] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0167] especially preferably hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxycarbonyl or
CONR.sup.9R.sup.10;
[0168] particularly preferably hydrogen or C.sub.1-C.sub.4-alkyl
such as methyl or ethyl;
[0169] very especially preferably hydrogen;
[0170] R.sup.6 is hydrogen or C.sub.1-C.sub.4-alkyl such as methyl
or ethyl;
[0171] especially preferably hydrogen.
[0172] 6. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I,
[0173] R.sup.7 is halogen, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalky- l, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl, amino, C.sub.1-C.sub.6-alkylamino,
di(C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkoxy)methyl,
formyl, C.sub.1-C.sub.4-alkylcarbonyl,
C.sub.1-C.sub.4-haloalkylcarbonyl, hydroxycarbonyl,
C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-haloalkoxycarbonyl
or CONR.sup.9R.sup.10;
[0174] especially preferably halogen such as chlorine or bromine,
C.sub.1-C.sub.4-alkyl such as methyl, ethyl, 1-methylethyl or
1,1-dimethylethyl, C.sub.1-C.sub.4-alkoxy, such as methoxy or
ethoxy, C.sub.1-C.sub.4-alkylthio such as methylthio or ethylthio,
C.sub.1-C.sub.4-alkylsulfinyl such as methylsulfinyl or
ethylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl such as methylsulfonyl
or ethylsulfonyl, amino, C.sub.1-C.sub.4-alkylamino such as
methylamino or ethylamino, di(C.sub.1-C.sub.4-alkyl)amino such as
dimethylamino or diethylamino, di(C.sub.1-C.sub.4-alkoxy)methyl
such as dimethoxymethyl or diethoxymethyl,
C.sub.1-C.sub.4-alkylcarbonyl such as methylcarbonyl or
ethylcarbonyl, hydroxycarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl such
as methoxycarbonyl or ethoxycarbonyl or CONR.sup.9R.sup.10;
[0175] particularly preferably C.sub.1-C.sub.4-alkyl such as
methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,
C.sub.1-C.sub.4-alkylcarbonyl such as methylcarbonyl or
ethylcarbonyl, hydroxycarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl
such as methoxycarbonyl or ethoxycarbonyl;
[0176] very especially preferably C.sub.1-C.sub.4-alkyl such as
methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl, hydroxycarbonyl
or C.sub.1-C.sub.4-alkoxycarbonyl or ethoxycarbonyl;
[0177] very particularly preferably C.sub.1-C.sub.4-alkyl such as
methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl.
[0178] 7. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I,
[0179] R.sup.12 is hydroxyl, OR.sup.19 or SR.sup.19; and
[0180] R.sup.19 is C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.20-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-alkylthiocarbonyl, it being possible for the alkyl
and alkoxy radicals to be partially or fully halogenated and/or to
have attached to them one, two or three substituents selected from
among cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl or
C.sub.3-C.sub.6-cycloalkyl;
[0181] phenyl, phenyl-C.sub.1-C.sub.4-alkyl,
phenylcarbonyl-C.sub.1-C.sub.- 4-alkyl, phenylcarbonyl,
phenoxycarbonyl, heterocyclyl, heterocyclyl-C.sub.1-C.sub.4-alkyl,
heterocyclylcarbonyl-C.sub.1-C.sub.4-- alkyl,
heterocyclyloxycarbonyl, it being possible for the phenyl or
heterocyclyl radical of the abovementioned radicals to be partially
or fully halogenated and/or to have attached to it one, two or
three substituents selected from among nitro, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy.
[0182] Heterocyclyl (alone or in combination) is preferably a
5-membered unsaturated ring or a 6-membered unsaturated ring, in
particular pyridin-2-yl or pyridin-3-yl.
[0183] Especially preferably heterocyclyl (alone or in combination)
is 5-membered unsaturated rings wth a hetero atom such as 2-furyl,
3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;
[0184] very especially preferably heterocyclyl is 2-thienyl or
3-thienyl.
[0185] 8. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I, R.sup.12 is hydroxyl.
[0186] 9. In a further preferred embodiment of the
3-(4,5-dihydroisoxazol-- 5-yl)benzoylcyclohexenones of the formula
I,
[0187] R.sup.13 and R.sup.17 are hydrogen, C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkylthio;
[0188] R.sup.14, R.sup.16, R.sup.18 are hydrogen or methyl;
[0189] R.sup.15 is hydrogen, hydroxyl, C.sub.1-C.sub.6-alkyl or
di(C.sub.1-C.sub.6-alkoxy)methyl;
[0190] or
[0191] R.sup.13 and R.sup.14 or R.sup.14 and R.sup.15 or R.sup.15
and R.sup.16 or R.sup.14 and R.sup.18 or R.sup.17 and R.sup.18
together are C.sub.1-C.sub.5-alkanediyl which can have attached to
it one, two or three substituents selected from among halogen,
cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0192] or
[0193] R.sup.15 and R.sup.16 together are an oxygen atom.
[0194] Particularly preferably,
[0195] R.sup.13, R.sup.17 are hydrogen or
C.sub.1-C.sub.4-alkyl;
[0196] R.sup.14, R.sup.16, R.sup.18 are hydrogen or methyl;
[0197] R.sup.15 is hydrogen, C.sub.1-C.sub.6-alkyl or
di(C.sub.1-C.sub.6-alkoxy)methyl;
[0198] very especially preferably hydrogen or
C.sub.1-C.sub.6-alkyl;
[0199] or
[0200] R.sup.14 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl which can have attached to it one, two
or three substituents selected from among halogen, cyano,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or
C.sub.1-C.sub.4-alkoxycarbonyl;
[0201] or
[0202] R.sup.15 and R.sup.16 together are an oxygen atom.
[0203] Very particularly especially preferred are the
3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula
Ia1(.ident.I where R.sup.1.dbd.Cl; R.sup.2.dbd.SO.sub.2CH.sub.3;
R.sup.3, R.sup.4, R.sup.15 to R.sup.18.dbd.H; R.sup.12.dbd.OH), in
particular the compounds Ia1.1 to Ia1.64, the definitions of
radicals R.sup.1 to R.sup.14 having a special meaning for the
compounds according to the invention, not only in combination with
each other, but also in each case by themselves.
1TABLE 1 Ia1 3 No. R.sup.5 R.sup.6 R.sup.7 Ia1.l H H CH.sub.3 Ia1.2
Cl H CH.sub.3 Ia1.3 Br H CH.sub.3 Ia1.4 CN H CH.sub.3 Ia1.5
NO.sub.2 H CH.sub.3 Ia1.6 CH.sub.3 H CH.sub.3 Ia1.7
CH.sub.2CH.sub.3 H CH.sub.3 Ia1.8 CH(CH.sub.3).sub.2 H CH.sub.3
Ia1.9 C(CH.sub.3).sub.3 H CH.sub.3 Ia1.10 CHO H CH.sub.3 Ia1.11
CH.dbd.NOH H CH.sub.3 Ia1.12 CH.dbd.NOCH.sub.3 H CH.sub.3 Ia1.13
CH.dbd.NOCH.sub.2CH.sub.3 H CH.sub.3 Ia1.14 COCH.sub.3 H CH.sub.3
Ia1.15 C(.dbd.NOH)CH.sub.3 H CH.sub.3 Ia1.16
C(.dbd.NOCH.sub.3)CH.sub.3 H CH.sub.3 Ia1.17
C(.dbd.NOCH.sub.2CH.sub.3)CH.sub.3 H CH.sub.3 Ia1.18
CH.dbd.NN(CH.sub.3).sub.2 H CH.sub.3 Ia1.19
C[.dbd.NN(CH.sub.3).sub.2]CH.sub.3 H CH.sub.3 Ia1.20 COOH H
CH.sub.3 Ia1.21 COOCH.sub.3 H CH.sub.3 Ia1.22 COOCH.sub.2CH.sub.3 H
CH.sub.3 Ia1.23 OCH.sub.3 H CH.sub.3 Ia1.24 OCH.sub.2CH.sub.3 H
CH.sub.3 Ia1.25 SCH.sub.3 H CH.sub.3 Ia1.26 CH.sub.2F H CH.sub.3
Ia1.27 CHF.sub.2 H CH.sub.3 Ia1.28 CF.sub.3 H CH.sub.3 Ia1.29
CF.sub.2CF.sub.3 H CH.sub.3 Ia1.30 CH.sub.2Cl H CH.sub.3 Ia1.31
CH.sub.2CN H CH.sub.3 la1.32 CH.sub.2--CH.sub.2 CH.sub.3 Ia1.33
CH.sub.2--CH.sub.2--CH.sub.2 CH.sub.3 la1.34
CH.sub.2--CH.sub.2--CH.sub.2--CH.sub.2 CH.sub.3 la1.35
CH.sub.2--CH.sub.2--CH.sub.2--CH.sub.2--CH.sub.2 CH.sub.3 Ia1.36
CH.sub.3 CH.sub.3 CH.sub.3 Ia1.37 CH.sub.3 CH.sub.2CH.sub.3
CH.sub.3 Ia1.38 CF.sub.3 COCH.sub.3 CH.sub.3 Ia1.39 CF.sub.3
COOCH.sub.3 CH.sub.3 Ia1.40 CN COCH.sub.3 CH.sub.3 Ia1.41 CN
COOCH.sub.3 CH.sub.3 Ia1.42 CN CN CH.sub.3 Ia1.43 COCH.sub.3
COCH.sub.3 CH.sub.3 Ia1.44 COCH.sub.3 COOCH.sub.3 CH.sub.3 Ia1.45 H
H CH.sub.2CH.sub.3 Ia1.46 H H CH(CH.sub.3).sub.2 Ia1.47 H H
C(CH.sub.3).sub.3 Ia1.48 H H Cl Ia1.49 H H OCH.sub.3 Ia1.50 H H
SCH.sub.3 Ia1.51 H H SOCH.sub.3 Ia1.52 H H SO.sub.2CH.sub.3 Ia1.53
H H CN Ia1.54 H H CHO Ia1.55 H H CH.dbd.NOH Ia1.56 H H
CH.dbd.NOCH.sub.3 Ia1.57 H H CH.dbd.NOCH.sub.2CH.sub.3 Ia1.58 H H
COCH.sub.3 Ia1.59 H H C(.dbd.NOH)CH.sub.3 Ia1.60 H H
C(.dbd.NOCH.sub.3)CH.sub.3 Ia1.61 H H COOH Ia1.62 H H COOCH.sub.3
Ia1.63 H H COOCH.sub.2CH.sub.3 Ia1.64 H H
CH(OCH.sub.2CH.sub.3).sub.2 Equally particularly preferred are the
compounds Ia2., especially the compounds Ia2.1-Ia2.64, which differ
from the compounds Ia1.1-Ia1.64 by the fact that R.sup.15 is
methyl.
[0204] 4
[0205] Equally particularly preferred are the compounds Ia3.,
especially the compounds Ia3.1-Ia3.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.15 and R.sup.16 are
methyl. 5
[0206] Equally particularly preferred are the compounds Ia4.,
especially the compounds la4.1-Ia4.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.13 and R.sup.17 are
methyl. 6
[0207] Equally particularly preferred are the compounds Ia5.,
especially the compounds Ia5.1-Ia5.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.13 is methylthio and
R.sup.14 is methyl. 7
[0208] Equally particularly preferred are the compounds Ia6.,
especially the compounds Ia6.1-Ia6.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.14 and R.sup.18
together are ethane-1,2-diyl. 8
[0209] Equally particularly preferred are the compounds Ia7.,
especially the compounds Ia7.1-Ia7.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.13, R.sup.14,
R.sup.17 and R.sup.18 are methyl and R.sup.15 and R.sup.16 are
oxygen. 9
[0210] Equally particularly preferred are the compounds Ia8.,
especially the compounds Ia8.1-Ia8.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.15 is hydroxyl.
10
[0211] Equally particularly preferred are the compounds Ia9.,
especially the compounds Ia9.1-Ia9.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl. 11
[0212] Equally particularly preferred are the compounds Ia10.,
especially the compounds Ia10.1-Ia10.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.15 are
methyl. 12
[0213] Equally particularly preferred are the compounds Ia11.,
especially the compounds Ia11.1-Ia11.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.15 and
R.sup.16 are methyl. 13
[0214] Equally particularly preferred are the compounds Ia12.,
especially the compounds Ia12.1-Ia12.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13 and
R.sup.17 are methyl. 14
[0215] Equally particularly preferred are the compounds Ia13.,
especially the compounds Ia13.1-Ia13.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.14 are
methyl and R.sup.13 is methylthio. 15
[0216] Equally particularly preferred are the compounds la14.,
especially the compounds Ia14.1-Ia14.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl and
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 16
[0217] Equally particularly preferred are the compounds Ia15.,
especially the compounds Ia15.1-Ia15.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15 and
R.sup.16 are oxygen. 17
[0218] Equally particularly preferred are the compounds Ia16.,
especially the compounds Ia16.1-Ia16.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl and
R.sup.15 is hydroxyl. 18
[0219] Equally particularly preferred are the compounds Ia17.,
especially the compounds Ia17.1-Ia17.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl.
19
[0220] Equally particularly preferred are the compounds Ia18.,
especially the compounds Ia18.1-Ia18.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.15 is methyl. 20
[0221] Equally particularly preferred are the compounds Ia19.,
especially the compounds Ia19.1 -Ia19.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.15 and R.sup.16 are methyl. 21
[0222] Equally particularly preferred are the compounds Ia20.,
especially the compounds Ia20.1-Ia20.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.13 and R.sup.17 are methyl. 22
[0223] Equally particularly preferred are the compounds Ia21.,
especially the compounds Ia21.1-Ia21.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.13 is methylthio and R.sup.14 is methyl. 23
[0224] Equally particularly preferred are the compounds Ia22.,
especially the compounds Ia22.1-Ia22.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 24
[0225] Equally particularly preferred are the compounds Ia23.,
especially the compounds Ia23.1-Ia23.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.16
is oxygen. 25
[0226] Equally particularly preferred are the compounds Ia24.,
especially the compounds Ia24.1-Ia24.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.15 is hydroxyl. 26
[0227] Equally particularly preferred are the compounds Ia25.,
especially the compounds Ia25.1-Ia25.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy. 27
[0228] Equally particularly preferred are the compounds Ia26.,
especially the compounds Ia26.1-Ia26.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.15 is methyl. 28
[0229] Equally particularly preferred are the compounds Ia27.,
especially the compounds Ia27.1-Ia27.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.15 and R.sup.16 are methyl. 29
[0230] Equally particularly preferred are the compounds Ia28.,
especially the compounds Ia28.1-Ia28.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.13 and R.sup.17 are methyl. 30
[0231] Equally particularly preferred are the compounds Ia29.,
especially the compounds Ia29.1-Ia29.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy,
R.sup.13 is methylthio and R.sup.14 is methyl. 31
[0232] Equally particularly preferred are the compounds Ia30.,
especially the compounds Ia30.1-Ia30.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy,
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 32
[0233] Equally particularly preferred are the compounds Ia31.,
especially the compounds Ia31.1-Ia31.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy:
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15
and R.sup.16 together are oxygen. 33
[0234] Equally particularly preferred are the compounds Ia32.,
especially the compounds Ia32.1-Ia32.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.15 is hydroxyl. 34
[0235] Equally particularly preferred are the compounds Ia33.,
especially the compounds Ia33.1-Ia33.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl.
35
[0236] Equally particularly preferred are the compounds Ia34.,
especially the compounds Ia34.1-Ia34.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl
and R.sup.15 is methyl. 36
[0237] Equally particularly preferred are the compounds Ia35.,
especially the compounds Ia35.1-Ia35.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl
and R.sup.15 and R.sup.16 are methyl. 37
[0238] Equally particularly preferred are the compounds Ia36.,
especially the compounds Ia36.1-Ia36.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl
and R.sup.13 and R.sup.17 are methyl. 38
[0239] Equally particularly preferred are the compounds Ia37.,
especially the compounds Ia37.1-Ia37.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.13 is methylthio and R.sup.14 is methyl. 39
[0240] Equally particularly preferred are the compounds Ia38.,
especially the compounds Ia38.1-Ia38.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 40
[0241] Equally particularly preferred are the compounds Ia39.,
especially the compounds Ia39.1-Ia39.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15
and R.sup.16 together are oxygen. 41
[0242] Equally particularly preferred are the compounds Ia40.,
especially the compounds Ia40.1-Ia40.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl
and R.sup.15 is hydroxyl. 42
[0243] Equally particularly preferred are the compounds Ia41.,
especially the compounds Ia4.1-Ia41.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl and
R.sup.2 is ethylsulfonyl. 43
[0244] Equally particularly preferred are the compounds Ia42.,
especially the compounds Ia42.1-Ia42.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.15 are
methyl and R.sup.2 is ethylsulfonyl. 44
[0245] Equally particularly preferred are the compounds Ia43.,
especially the compounds Ia43.1-Ia43.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.15 and
R.sup.16 are ethyl and R.sup.2 is ethylsulfonyl. 45
[0246] Equally particularly preferred are the compounds Ia44.,
especially the compounds Ia44.1-Ia44.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13 and
R.sup.17 are methyl and R.sup.2 is ethylsulfonyl. 46
[0247] Equally particularly preferred are the compounds Ia45.,
especially the compounds Ia45.1-Ia45.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.14 are
methyl and R.sup.13 is methylthio. 47
[0248] Equally particularly preferred are the compounds Ia46.,
especially the compounds Ia46.1-Ia46.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is ethylsulfonyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 48
[0249] Equally particularly preferred are the compounds Ia47.,
especially the compounds Ia47.1-Ia47.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl, R.sup.2 is
ethylsulfonyl and R.sup.15 and R.sup.16 together are oxygen. 49
[0250] Equally particularly preferred are the compounds Ia48.,
especially the compounds Ia48.1-Ia48.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is ethylsulfonyl and R.sup.15 is hydroxyl. 50
[0251] Equally particularly preferred are the compounds Ia49.,
especially the compounds Ia49.1-Ia49.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.2 is ethylsulfonyl. 51
[0252] Equally particularly preferred are the compounds Ia50.,
especially the compounds Ia50.1-Ia50.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl and R.sup.15 is methyl. 52
[0253] Equally particularly preferred are the compounds Ia51.,
especially the compounds Ia51.1-Ia51.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl and R.sup.15 and R.sup.16 are methyl.
53
[0254] Equally particularly preferred are the compounds Ia52.,
especially the compounds Ia52.1-Ia52.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl and R.sup.13 and R.sup.17 are methyl.
54
[0255] Equally particularly preferred are the compounds Ia53.,
especially the compounds Ia53.1-Ia53.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl, R.sup.13 is methylthio and R.sup.14 is
methyl. 55
[0256] Equally particularly preferred are the compounds Ia54.,
especially the compounds Ia54.1-Ia54.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 56
[0257] Equally particularly preferred are the compounds Ia55.,
especially the compounds Ia55.1-Ia55.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl, R.sup.13, R.sup.14, R.sup.17 and R.sup.18
are methyl and R.sup.15 and R.sup.16 together are oxygen. 57
[0258] Equally particularly preferred are the compounds Ia56.,
especially the compounds Ia56.1-Ia56.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is ethylsulfonyl and R.sup.15 is hydroxyl. 58
[0259] Equally particularly preferred are the compounds Ia57.,
especially the compounds Ia57.1-Ia57.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.2 is ethylsulfonyl. 59
[0260] Equally particularly preferred are the compounds Ia58.,
especially the compounds Ia58.1-Ia58.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl and R.sup.15 is methyl. 60
[0261] Equally particularly preferred are the compounds Ia59.,
especially the compounds Ia59.1-Ia59.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl and R.sup.15 and R.sup.16 are methyl. 61
[0262] Equally particularly preferred are the compounds Ia60.,
especially the compounds Ia60.1-Ia60.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl and R.sup.13 and R.sup.17 are methyl. 62
[0263] Equally particularly preferred are the compounds Ia61.,
especially the compounds Ia61.1-Ia61.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl, R.sup.13 is methylthio and R.sup.14 is methyl.
63
[0264] Equally particularly preferred are the compounds Ia62.,
especially the compounds Ia62.1-Ia62.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 64
[0265] Equally particularly preferred are the compounds Ia63.,
especially the compounds Ia63.1-Ia63.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is ethylsulfonyl, R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are
methyl and R.sup.15 and R.sup.16 together are oxygen. 65
[0266] Equally particularly preferred are the compounds Ia64.,
especially the compounds Ia64.1-Ia64.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that RI is methoxy, R.sup.2 is
ethylsulfonyl and R.sup.15 is hydroxyl. 66
[0267] Equally particularly preferred are the compounds Ia65.,
especially the compounds Ia65.1-Ia65.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine. 67
[0268] Equally particularly preferred are the compounds Ia66.,
especially the compounds Ia66.1-Ia66.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine and
R.sup.15 is methyl. 68
[0269] Equally particularly preferred are the compounds Ia67.,
especially the compounds Ia67.1-Ia67.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine and
R.sup.15 and R.sup.16 are methyl. 69
[0270] Equally particularly preferred are the compounds Ia68.,
especially the compounds Ia68.1-Ia68.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine and
R.sup.13 and R.sup.17 are methyl. 70
[0271] Equally particularly preferred are the compounds Ia69.,
especially the compounds Ia69.1-Ia69.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine,
R.sup.13 is methylthio and R.sup.14 is methyl. 71
[0272] Equally particularly preferred are the compounds Ia70.,
especially the compounds Ia70.1-Ia70.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine and
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 72
[0273] Equally particularly preferred are the compounds Ia71.,
especially the compounds Ia71.1-Ia71.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine,
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15
and R.sup.16 together are oxygen. 73
[0274] Equally particularly preferred are the compounds Ia72.,
especially the compounds Ia72.1-Ia72.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is chlorine and
R.sup.15 is hydroxyl. 74
[0275] Equally particularly preferred are the compounds Ia73.,
especially the compounds Ia73.1-Ia73.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl and
R.sup.2 is chlorine. 75
[0276] Equally particularly preferred are the compounds Ia74.,
especially the compounds la74.1-Ia74.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.15 are
methyl and R.sup.2 is chlorine. 76
[0277] Equally particularly preferred are the compounds Ia75.,
especially the compounds Ia75.1-Ia75.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.15 and
R.sup.18 are methyl and R.sup.2 is chlorine. 77
[0278] Equally particularly preferred are the compounds Ia76.,
especially the compounds Ia76.1-Ia76.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13 and
R.sup.17 are methyl and R.sup.2 is chlorine. 78
[0279] Equally particularly preferred are the compounds Ia77.,
especially the compounds Ia77.1-Ia77.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.14 are
methyl, R.sup.2 is chlorine and R.sup.13 is methylthio. 79
[0280] Equally particularly preferred are the compounds Ia78.,
especially the compounds Ia78.1-Ia78.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is chlorine and R.sup.14 and R.sup.18 together are ethane-1,2-diyl.
80
[0281] Equally particularly preferred are the compounds Ia79.,
especially the compounds Ia79.1-Ia79.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl, R.sup.2 is chlorine and
R.sup.15 and R.sup.16 together are oxygen. 81
[0282] Equally particularly preferred are the compounds Ia80.,
especially the compounds Ia80.1-Ia80.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is chlorine and R.sup.15 is hydroxyl. 82
[0283] Equally particularly preferred are the compounds Ia81.,
especially the compounds Ia81.1-Ia81.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl
and R.sup.2 is chlorine. 83
[0284] Equally particularly preferred are the compounds Ia82.,
especially the compounds Ia82.1-Ia82.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine and R.sup.15 is methyl. 84
[0285] Equally particularly preferred are the compounds Ia83.,
especially the compounds Ia83.1-Ia83.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine and R.sup.15 and R.sup.16 are methyl. 85
[0286] Equally particularly preferred are the compounds Ia84.,
especially the compounds Ia84.1-Ia84.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine and R.sup.13 and R.sup.17 are methyl. 86
[0287] Equally particularly preferred are the compounds Ia85.,
especially the compounds Ia85.1-Ia85.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine, R.sup.13 is methylthio and R.sup.14 is methyl.
87
[0288] Equally particularly preferred are the compounds Ia86.,
especially the compounds Ia86.1-Ia86.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 88
[0289] Equally particularly preferred are the compounds Ia87.,
especially the compounds Ia87.1-Ia87.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine, R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are
methyl and R.sup.15 and R.sup.16 together are oxygen. 89
[0290] Equally particularly preferred are the compounds Ia88.,
especially the compounds Ia88.1-Ia88.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is trifluoromethyl,
R.sup.2 is chlorine and R.sup.15 is hydroxyl. 90
[0291] Equally particularly preferred are the compounds Ia89.,
especially the compounds Ia89.1-Ia89.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.2 is chlorine. 91
[0292] Equally particularly preferred are the compounds Ia90.,
especially the compounds Ia90.1-Ia90.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine and R.sup.15 is methyl. 92
[0293] Equally particularly preferred are the compounds Ia91.,
especially the compounds Ia91.1-Ia91.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine and R.sup.15 and R.sup.16 are methyl. 93
[0294] Equally particularly preferred are the compounds Ia92.,
especially the compounds Ia92.1-Ia92.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that RI is methoxy, R.sup.2 is
chlorine and R.sup.13 and R.sup.17 are methyl. 94
[0295] Equally particularly preferred are the compounds Ia93.,
especially the compounds Ia93.1-Ia93.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine, R.sup.13 is methylthio and R.sup.14 is methyl. 95
[0296] Equally particularly preferred are the compounds Ia94.,
especially the compounds Ia94.1-Ia94.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine and R.sup.14 and R.sup.18 together are ethane-1,2-diyl.
96
[0297] Equally particularly preferred are the compounds Ia95.,
especially the compounds Ia95.1-Ia95.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine, R.sup.13, R.sup.14, R.sup.12 and R.sup.18 are methyl
and R.sup.15 and R.sup.16 together are oxygen. 97
[0298] Equally particularly preferred are the compounds Ia96.,
especially the compounds Ia96.1-Ia96.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is chlorine and R.sup.15 is hydroxyl. 98
[0299] Equally particularly preferred are the compounds Ia97.,
especially the compounds Ia97.1-Ia97.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl.
99
[0300] Equally particularly preferred are the compounds Ia98.,
especially the compounds Ia98.1-Ia98.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl
and R.sup.15 is methyl. 100
[0301] Equally particularly preferred are the compounds Ia99.,
especially the compounds Ia99.1-Ia99.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl
and R.sup.15 and R.sup.16 are methyl. 101
[0302] Equally particularly preferred are the compounds Ia100.,
especially the compounds Ia100.1-Ia101.64 which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl
and R.sup.13 and R.sup.17 are methyl. 102
[0303] Equally particularly preferred are the compounds Ia101.,
especially the compounds Ia101.1-Ia101.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl,
R.sup.13 is methylthio and R.sup.14 is methyl. 103
[0304] Equally particularly preferred are the compounds Ia102.,
especially the compounds Ia102.1-Ia102.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl
and R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 104
[0305] Equally particularly preferred are the compounds Ia103.,
especially the compounds Ia103.1-Ia103.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl,
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15
and R.sup.16 together are oxygen. 105
[0306] Equally particularly preferred are the compounds Ia104.,
especially the compounds Ia104.1-Ia104.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is trifluoromethyl
and R.sup.15 is hydroxyl. 106
[0307] Equally particularly preferred are the compounds Ia105.,
especially the compounds Ia105.1-Ia105.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl and
R.sup.2 is trifluoromethyl. 107
[0308] Equally particularly preferred are the compounds Ia106.,
especially the compounds Ia106.1-Ia106.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.15 are
methyl and R.sup.2 is trifluoromethyl. 108
[0309] Equally particularly preferred are the compounds Ia107.,
especially the compounds Ia107.1-Ia107.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.15 and
R.sup.16 are methyl and R.sup.2 is trifluoromethyl. 109
[0310] Equally particularly preferred are the compounds Ia108.,
especially the compounds Ia108.1-Ia108.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13 and
R.sup.17 are methyl and R.sup.2 is trifluoromethyl. 110
[0311] Equally particularly preferred are the compounds Ia109.,
especially the compounds Ia109.1-Ia109.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.14 are
methyl, R.sup.2 is trifluoromethyl and R.sup.13 is methylthio.
111
[0312] Equally particularly preferred are the compounds Ia110.,
especially the compounds Ia110.1-Ia110.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is trifluoromethyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 112
[0313] Equally particularly preferred are the compounds Ia111.,
especially the compounds Ia111.1-Ia111.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl, R.sup.2 is
trifluoromethyl and R.sup.15 and R.sup.16 together are oxygen.
113
[0314] Equally particularly preferred are the compounds Ia112.,
especially the compounds Ia112.1-Ia112.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methyl, R.sup.2
is trifluoromethyl and R.sup.15 is hydroxyl. 114
[0315] Equally particularly preferred are the compounds Ia113.,
especially the compounds Ia113.1-Ia113.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl. 115
[0316] Equally particularly preferred are the compounds Ia114.,
especially the compounds Ia114.1-Ia114.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl and R.sup.15 is methyl. 116
[0317] Equally particularly preferred are the compounds Ia115.,
especially the compounds Ia115.1-Ia115.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl and R.sup.15 and R.sup.16 are methyl. 117
[0318] Equally particularly preferred are the compounds Ia116.,
especially the compounds Ia116.1-Ia116.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl and R.sup.13 and R.sup.17 are methyl. 118
[0319] Equally particularly preferred are the compounds Ia117.,
especially the compounds Ia117.1-Ia117.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl, R1.sup.3 is methylthio and R.sup.14 is methyl.
119
[0320] Equally particularly preferred are the compounds Ia118.,
especially the compounds Ia118.1-Ia118.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 120
[0321] Equally particularly preferred are the compounds Ia119.,
especially the compounds Ia119.1-Ia119.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl, R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are
methyl and R.sup.15 and R.sup.16 together are oxygen. 121
[0322] Equally particularly preferred are the compounds Ia120.,
especially the compounds Ia120.l -Ia120.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.2 are
trifluoromethyl and R.sup.15 is hydroxyl. 122
[0323] Equally particularly preferred are the compounds Ia121.,
especially the compounds Ia121.1-Ia121.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy and
R.sup.2 is trifluoromethyl. 123
[0324] Equally particularly preferred are the compounds Ia122.,
especially the compounds Ia122.1-Ia122.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl and R.sup.15 is methyl. 124
[0325] Equally particularly preferred are the compounds Ia123.,
especially the compounds Ia123.1-Ia123.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl and R.sup.15 and R.sup.16 are methyl. 125
[0326] Equally particularly preferred are the compounds Ia124.,
especially the compounds Ia124.1-Ia124.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl and R.sup.13 and R.sup.17 are methyl. 126
[0327] Equally particularly preferred are the compounds Ia125.,
especially the compounds Ia125.1-Ia125.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl, R.sup.13 is methylthio and R.sup.14 is methyl.
127
[0328] Equally particularly preferred are the compounds Ia126.,
especially the compounds Ia126.1-Ia126.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 128
[0329] Equally particularly preferred are the compounds Ia127.,
especially the compounds Ia127.1-Ia127.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl, R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are
methyl and R.sup.15 and R.sup.16 together are oxygen. 129
[0330] Equally particularly preferred are the compounds Ia128.,
especially the compounds Ia128.1-Ia128.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 is methoxy, R.sup.2
is trifluoromethyl and R.sup.15 is hydroxyl. 130
[0331] Equally particularly preferred are the compounds Ia129.,
especially the compounds Ia129.1-Ia129.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine.
131
[0332] Equally particularly preferred are the compounds Ia130.,
especially the compounds Ia130.1-Ia130.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine and
R.sup.15 is methyl. 132
[0333] Equally particularly preferred are the compounds Ia131.,
especially the compounds Ia131.1-Ia131.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine and
R.sup.15 and R.sup.16 are methyl. 133
[0334] Equally particularly preferred are the compounds Ia132.,
especially the compounds Ia132.1-Ia132.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine and
.sup.13 and R.sup.17 are methyl. 134
[0335] Equally particularly preferred are the compounds Ia133.,
especially the compounds Ia133.1-Ia133.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine,
R.sup.13 is methylthio and R.sup.14 is methyl. 135
[0336] Equally particularly preferred are the compounds Ia134.,
especially the compounds Ia134.1-Ia134.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine and
R.sup.14 and R.sup.18 together are ethane-1,2-diyl. 136
[0337] Equally particularly preferred are the compounds Ia135.,
especially the compounds Ia135.1-Ia135.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine,
R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15
and R.sup.16 together are oxygen. 137
[0338] Equally particularly preferred are the compounds Ia136.,
especially the compounds Ia136.1-Ia136.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.3 is chlorine and
R.sup.15 is hydroxyl. 138
[0339] Equally particularly preferred are the compounds Ia137.,
especially the compounds Ia137.1-Ia137.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl
and R.sup.3 is chlorine. 139
[0340] Equally particularly preferred are the compounds Ia138.,
especially the compounds Ia138.1-Ia138.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine and R.sup.15 is methyl. 140
[0341] Equally particularly preferred are the compounds Ia139.,
especially the compounds Ia139.1-Ia139.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine and R.sup.15 and R.sup.16 are methyl. 141
[0342] Equally particularly preferred are the compounds Ia140.,
especially the compounds Ia140.l -Ia140.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine and R.sup.13 and R.sup.17 are methyl. 142
[0343] Equally particularly preferred are the compounds Ia141.,
especially the compounds Ia141.1-Ia141.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine, R.sup.13 is methylthio and R.sup.14 is methyl.
143
[0344] Equally particularly preferred are the compounds Ia142.,
especially the compounds Ia142.1-Ia142.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 144
[0345] Equally particularly preferred are the compounds Ia143.,
especially the compounds Ia143.1-Ia143.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine, R.sup.13, R.sup.14, R.sup.17 and R.sup.18 are
methyl and R.sup.15 and R.sup.16 together are oxygen. 145
[0346] Equally particularly preferred are the compounds Ia144.,
especially the compounds Ia144.1-Ia144.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.2 is ethylsulfonyl,
R.sup.3 is chlorine and R.sup.15 is hydroxyl. 146
[0347] Equally particularly preferred are the compounds Ia145.,
especially the compounds Ia14.51-Ia145.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl. 147
[0348] Equally particularly preferred are the compounds Ia146.,
especially the compounds Ia146.1-Ia146.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 and
R.sup.15 are methyl. 148
[0349] Equally particularly preferred are the compounds Ia147.,
especially the compounds Ia147.1-Ia147.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.15
and R.sup.16 are methyl. 149
[0350] Equally particularly preferred are the compounds Ia148.,
especially the compounds Ia148.1-Ia148.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13
and R.sup.17 are methyl. 150
[0351] Equally particularly preferred are the compounds Ia149.,
especially the compounds Ia149.1-Ia149.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 and
R.sup.14 are methyl and R.sup.13 is methylthio. 151
[0352] Equally particularly preferred are the compounds Ia150.,
especially the compounds Ia150.1-Ia150.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl and R.sup.14 and R.sup.18 together are ethane-1,2-diyl.
152
[0353] Equally particularly preferred are the compounds Ia151.,
especially the compounds Ia151.1-Ia151.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl and R.sup.15 and
R.sup.16 together are oxygen. 153
[0354] Equally particularly preferred are the compounds Ia152.,
especially the compounds Ia152.1-Ia152.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl and R.sup.15 is hydroxyl. 154
[0355] Equally particularly preferred are the compounds Ia153.,
especially the compounds Ia153.1-Ia153.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl and R.sup.2 is ethylsulfonyl. 155
[0356] Equally particularly preferred are the compounds Ia154.,
especially the compounds Ia154.1-Ia154.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 and
R.sup.15 are methyl and R.sup.2 is ethylsulfonyl. 156
[0357] Equally particularly preferred are the compounds Ia155.,
especially the compounds Ia155.1-Ia155.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.15
and R.sup.16 are methyl and R.sup.2 is ethylsulfonyl. 157
[0358] Equally particularly preferred are the compounds Ia156.,
especially the compounds Ia156.1-Ia156.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13
and R.sup.17 are methyl and R.sup.2 is ethylsulfonyl. 158
[0359] Equally particularly preferred are the compounds Ia157.,
especially the compounds Ia157.1-Ia157.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 an&
R.sup.14 are methyl, R.sup.2 is ethylsulfonyl and R.sup.13 is
methylthio. 159
[0360] Equally particularly preferred are the compounds Ia158.,
especially the compounds Ia158.1-Ia158.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl, R.sup.2 is ethylsulfonyl and R.sup.14 and R.sup.18 together
are ethane-1,2-diyl. 160
[0361] Equally particularly preferred are the compounds Ia159.,
especially the compounds Ia159.1-Ia159.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl, R.sup.2 is
ethylsulfonyl and R.sup.15 and R.sup.16 together are oxygen.
161
[0362] Equally particularly preferred are the compounds Ia160.,
especially the compounds Ia160.1-Ia160.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl, R.sup.2 is ethylsulfonyl and R.sup.15 is hydroxyl. 162
[0363] Equally particularly preferred are the compounds Ia161.,
especially the compounds Ia161.1-Ia161.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl and R.sup.2 is chlorine. 163
[0364] Equally particularly preferred are the compounds Ia162.,
especially the compounds Ia162.1-Ia162.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 and
R.sup.15 are methyl and R.sup.2 is chlorine. 164
[0365] Equally particularly preferred are the compounds Ia163.,
especially the compounds Ia163.1-Ia163.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.15
and R.sup.16 are methyl and R.sup.2 is chlorine. 165
[0366] Equally particularly preferred are the compounds Ia164.,
especially the compounds Ia164.1-Ia164.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13
and R.sup.17 are methyl and R.sup.2 is chlorine. 166
[0367] Equally particularly preferred are the compounds Ia165.,
especially the compounds Ia165.1-Ia165.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3 and
R.sup.14 are methyl, R.sup.2 is chlorine and R.sup.13 is
methylthio. 167
[0368] Equally particularly preferred are the compounds Ia166.,
especially the compounds Ia166.1-Ia166.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl, R.sup.2 is chlorine and R.sup.14 and R.sup.18 together are
ethane-1,2-diyl. 168
[0369] Equally particularly preferred are the compounds Ia167.,
especially the compounds Ia167.1-Ia167.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1, R.sup.3, R.sup.13,
R.sup.14, R.sup.17 and R.sup.18 are methyl, R.sup.2 is chlorine and
R.sup.15 and R.sup.16 together are oxygen. 169
[0370] Equally particularly preferred are the compounds Ia168.,
especially the compounds Ia168.1-Ia168.64, which differ from the
compounds Ia1.1-Ia1.64 by the fact that R.sup.1 and R.sup.3 are
methyl and R.sup.15 is hydroxyl. 170
[0371] In a further preferred embodiment of the compounds of the
formula I, the variables, either alone or in combination, have the
following meanings:
[0372] R.sup.1 is halogen, C.sub.1-C.sub.6-alkyl or
C.sub.1-C.sub.6-alkoxy;
[0373] preferably halogen such as chlorine or bromine,
C.sub.1-C.sub.4-alkyl such as methyl, ethyl or propyl,
C.sub.1-C.sub.4-alkoxy such as methoxy or ethoxy;
[0374] especially preferably chlorine, methyl or methoxy;
[0375] R.sup.2 is halogen or C.sub.1-C.sub.6-alkylsulfonyl;
[0376] preferably halogen such as chlorine or bromine or
C.sub.1-C.sub.4-alkylsulfonyl such as methylsulfonyl or
ethylsulfonyl;
[0377] especially preferably chlorine or methylsulfonyl;
[0378] R.sup.3 is hydrogen;
[0379] R hu 4 is hydrogen;
[0380] R.sup.5 is hydrogen;
[0381] R.sup.6 is hydrogen;
[0382] R.sup.7 is C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.4-alkylcarbonyl or C.sub.1-C.sub.4-alkoxycarbonyl;
preferably C.sub.1-C.sub.6-alkyl such as methyl, ethyl,
1-methylethyl or 1,1-dimethylethyl, methylcarbonyl or
ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl;
[0383] R.sup.12 is hydroxyl;
[0384] R.sup.13 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0385] R.sup.14 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0386] R.sup.15 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0387] R.sup.16 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0388] R.sup.17 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0389] R.sup.18 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0390] or
[0391] R.sup.15 and R.sup.16 together are an oxygen atom;
[0392] or
[0393] R.sup.14 and R.sup.18 together are
C.sub.1-C.sub.5-alkanediyl, in particular 1,2-ethanediyl.
[0394] The 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the
formula I can be obtained by various routes, for example by the
following process:
[0395] Process A:
[0396] Reaction of cyclohexenones of the formula II (where
R.sup.12.dbd.OH) with an activated carboxylic acid III.alpha. or a
carboxylic acid III.beta. which is preferably activated in situ, to
give the acylation product which is subsequently subjected to a
rearrangement reaction. 171
[0397] L.sup.1 is a nucleophilically displaceable leaving group
such as halogen, e.g. bromine or chlorine, hetaryl, e.g. imidazolyl
or pyridyl, carboxylate, e.g. acetate, trifluoroacetate and the
like.
[0398] The activated carboxylic acid can be employed directly, such
as in the case of the carbonyl halides, or generated in situ, for
example with dicyclohexylcarbodiimide,
triphenylphosphane/azodicarboxylic ester, 2-pyridine
disulfide/triphenylphosphane, carbonyldiimidazole and the like.
[0399] If appropriate, it may be advantageous to carry out the
acylation reaction in the presence of a base. The reactants and the
auxiliary base are expediently employed in equimolar amounts. An
excess of the auxiliary base, for example 1.2 to 2.5 mol
equivalents, especially 1.2 to 1.5 mol equivalents, based on II,
may be advantageous under certain circumstances.
[0400] Auxiliary bases which are suitable are tertiary alkylamines,
pyridine or alkali metal carbonates. Solvents which can be employed
are, for example, chlorinated hydrocarbons such as methylene
chloride, 1,2-dichloroethane, aromatic hydrocarbons such as
toluene, xylene, chlorobenzene, ethers such as diethyl ether,
methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic
solvents such as acetonitrile, dimethylformamide, dimethyl
sulfoxide, or esters such as ethyl acetate, or mixtures of
these.
[0401] If carbonyl halides are employed as activated carboxylic
acid component, it may be advantageous to cool the reaction mixture
to 0-10.degree. C. when adding this reactant. The mixture is
subsequently stirred at 20-100.degree. C., preferably at
25-50.degree. C., until the reaction is complete. Work-up is
carried out in the customary fashion, for example the reaction
mixture is poured into water and the product of interest is
extracted. 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 employed without further
purification in the rearrangement reaction.
[0402] Rearrangement of the esters to give the compounds of the
formula I is expediently carried out at temperatures of from 20 to
40.degree. C. in a solvent and in the presence of a base and, if
appropriate, with the aid of a cyano compound as catalyst.
[0403] Solvents which can be used are, for example, acetonitrile,
methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate,
toluene or mixtures of these. Preferred solvents are acetonitrile
and dioxane.
[0404] Suitable bases are tertiary amines such as triethylamine,
pyridine or alkali metal carbonates such as sodium carbonate or
potassium carbonate, which are preferably employed in equimolar
amounts or up to a four-fold excess based on the ester. By
preference, triethylamine or alkali metal carbonates are employed,
preferably in twice the equimolar ratio based on the ester.
[0405] Suitable cyano compounds are inorganic cyanides, such as
sodium cyanide, potassium cyanide and organic cyano compounds such
as acetone cyanohydrin or trimethylsilyl cyanide. They are employed
in an amount of 1 to 50 mol percent based on the ester. Preferably,
acetone cyanohydrin or trimethylsilyl cyanide are employed, for
example in an amount of 5 to 25, preferably 5 to 15, in particular
10, mol percent based on the ester.
[0406] Work-up can be carried out in a conventional manner. For
example, the reaction mixture is acidified 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.
[0407] (Examples of the synthesis of hydroxypyrazole esters and of
the rearrangement of the esters are given for example in EP-A 282
944 and U.S. Pat. No. 4,643,757).
[0408] Process B:
[0409] Reaction of
3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula I
(where R.sup.12.dbd.OH, SH) with a compound of the formula V:
172
[0410] L.sup.2 is a nucleophilically displaceable leaving group
such as halogen, e.g. bromine or chlorine, or hetaryl, e.g.
imidazolyl, pyridyl, sulfonate.
[0411] The compounds of the formula V can be employed directly,
such as, for example, in the case of the sulfonyl halides or
sulfonic anhydrides, or generated in situ, for example activated
sulfonic acids (by means of sulfonic acid and
dicyclohexylcarbonyldiimide, carbonyldiimidazole and the like).
[0412] As a rule, the starting compounds are employed in an
equimolar ratio. However, it may also be advantageous to employ one
or the other component in excess.
[0413] If appropriate, it may be advantageous to carry out the
reaction in the presence of a base. The reactants and the auxiliary
base are expediently employed in equimolar amounts. Under certain
circumstances, an excess of the auxiliary base, for example 1.5 to
3 mol equivalents based on II, may be advantageous.
[0414] Suitable auxiliary bases are tertiary alkylamines such as
triethylamine or pyridine, alkali metal carbonates, e.g. sodium
carbonate or potassium carbonate, and alkali metal hydrides, e.g.
sodium hydride. Triethylamine and pyridine are preferably used.
[0415] Examples of suitable solvents are chlorinated hydrocarbons
such as methylene chloride or 1,2-dichloroethane, aromatic
hydrocarbons, e.g. 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.
[0416] As a rule, the reaction temperature is in the range of from
0.degree. C. up to the boiling point of the reaction mixture.
[0417] Work-up can be carried out in a conventional manner to give
the product.
[0418] Process C:
[0419] Compounds of the formula I where R.sup.12=halogen are
obtained by reacting compounds of the formula I where
R.sup.12=hydroxyl with a halogenating agent (Hal represents
halogen). 173
[0420] Examples of suitable halogating agents are phosgene,
diphosgene, triphosgene, thionyl chloride, oxalyl chloride,
phosphorus oxychloride, phosphorus pentachloride, mesyl chloride,
chloromethylene-N,N-dimethylamm- onium chloride, oxalyl bromide,
phosphorus oxybromide and the like.
[0421] As a rule, the starting compounds are employed in an
equimolar ratio. It may also be advantageous to employ one or the
other component in excess.
[0422] Examples of suitable solvents are chlorinated hydrcarbons
such as methylene chloride or 1,2-dichloroethane, aromatic
hydrocarbons, e.g. toluene, xylene or chlorobenzene, polar aprotic
solvents such as acetonitrile, dimethylformamide or dimethyl
sulfoxide, or mixtures of these. It is also possible to carry out
the reaction without solvent.
[0423] As a rule, the reaction temperature is in the range of from
0.degree. C. up to the boiling point of the reaction mixture.
[0424] Work-up can be carried out in a conventional manner to give
the product.
[0425] Process D:
[0426] Compounds of the formula I where R.sup.12=mercapto,
OR.sup.19 or SR.sup.19 can be obtained by reacting compounds of the
formula I where R.sup.12=halogen with compounds VI in the presence
or absence of a base or with or without previous salt formation.
174
[0427] As a rule, the starting compounds are employed in an
equimolar ratio. However, it may also be advantageous to employ one
or the other component in excess.
[0428] If appropriate, it may also be advantageous to carry out the
reaction in the presence of a base. The reactants and the base are
expediently employed in equimolar quantities. An excess of base,
for example 1.5 to 3 mol equivalents based on I where R.sup.8=Hal,
may be advantageous under certain circumstances.
[0429] Bases which are suitable are tertiary alkylamines such as
triethylamine, aromatic amines such as pyridine, alkali metal
carbonates, e.g. sodium carbonate or potassium carbonate, alkali
metal hydrogen carbonates such as sodium hydrogen carbonate or
potassium hydrogen carbonate, alkali metal alkoxides such as sodium
methoxide, sodium ethoxide or potassium tert-butoxide, or alkali
metal hydrides such as e.g. sodium hydride. Sodium hydride or
potassium tert-butoxide are preferably used.
[0430] Examples of suitable solvents are chlorinated hydrocarbons
such as methylene chloride or 1,2-dichloroethane, aromatic
hydrocarbons, e.g. 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 mixtures of these.
[0431] As a rule, the reaction temperature is in the range of from
0.degree. C. up to the boiling point of the reaction mixture.
[0432] Work-up can be carried out in a conventional manner to give
the product.
[0433] Process E:
[0434] Moreover, compounds of the formula I where
R.sup.12.dbd.SOR.sup.20 or SO.sub.2R.sup.20 can be obtained by
reaction with an oxidant. 175
[0435] Examples of suitable oxidants are m-chloroperbenzoic acid,
peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide,
in the presence or absence of a catalyst such as tungstate.
[0436] As a rule, the starting compounds are employed in an
equimolar ratio. It may be advantageous to employ one or the other
component in excess.
[0437] Examples of suitable solvents are chlorinated hydrocarbons
such as methylene chloride or 1,2-dichloroethane, aromatic
hydrocarbons, e.g. toluene, xylene or chlorobenzene, ethers such as
diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane,
polar aprotic solvents such as acetonitrile or dimethylformamide,
or esters such as ethyl acetate, or mixtures of these.
[0438] As a rule, the reaction temperature is in the range of from
0.degree. C. up to the boiling point of the reaction mixture.
[0439] Work-up can be carried out in a conventional manner to give
the product.
[0440] The cyclohexenones of the formula II (where R.sup.12.dbd.OH)
which are used as starting materials are known or can be prepared
by conventional processes (for example EP-A 240 001 and J. Prakt.
Chem. 315, 383 (1973)).
[0441] 3-(4,5-Dihydroisoxazol-5-yl)carboxylic acid derivatives of
the formula III are novel, 176
[0442] the variables having the following meanings:
[0443] R.sup.1, R.sup.2 are hydrogen, nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl;
[0444] R.sup.3 is hydrogen, halogen or C.sub.1-C.sub.6-alkyl;
[0445] R.sup.4 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0446] R.sup.5, R.sup.6 are hydrogen, halogen, cyano, nitro,
C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkoxy)-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alky- l)amino-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1- -C.sub.4-alkyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0447] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0448] or
[0449] R.sup.5 and R.sup.6 together form a
C.sub.2-C.sub.6-alkanediyl chain which can be mono-to
tetrasubstituted by C.sub.1-C.sub.4-alkyl and/or can be interrupted
by oxygen or an unsubstituted or C.sub.1-C.sub.4-alkyl-substituted
nitrogen;
[0450] R.sup.7 is halogen, cyano, hydroxyl, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, amino,
C.sub.1-C.sub.6-alkylamino, di(C.sub.1-C.sub.6-alkyl)amino,
di(C.sub.1-C.sub.4-alkoxy)methyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C- .sub.4-alkyl or
COR.sup.8;
[0451] R.sup.8 is hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalk- yl, hydroxyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub- .4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy or NR.sup.9R.sup.10;
[0452] R.sup.9 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0453] R.sup.10 is C.sub.1-C.sub.4-alkyl;
[0454] R.sup.15 is hydroxyl or a radical which can be eliminated by
hydrolysis.
[0455] Examples of radicals which can be eliminated by hydrolysis
are alkoxy, phenoxy, alkylthio or phenylthio radicals which can be
unsubstituted or substituted, or halides, hetaryl radicals which
are bound via nitrogen, or amino, imino radicals which can be
unsubstituted or substituted, and the like.
[0456] Preferred are 3-(4,5-dihydroisoxazol-5-yl)carbonyl halides
of the formula III.alpha.' where L.sup.1=halogen ({circumflex over
(=)}III where R.sup.21=halogen), 177
[0457] where the variables R.sup.1 to R.sup.7 have the meanings
stated under formula III and
[0458] L.sup.1 is halogen, in particular chlorine or bromine.
[0459] Equally preferred are 3-(4,5-dihydroisoxazol-5-yl)carboxylic
acids of the formula III.beta. ({circumflex over (=)}III where
R.sup.21=hydroxyl), 178
[0460] where the variables R.sup.1 to R.sup.7 have the meanings
stated under formula III.
[0461] Equally preferred are 3-(4,5-dihydroisoxazol-5-yl)carboxylic
esters of the formula III.gamma. ({circumflex over (=)}III where
R.sup.21.dbd.C.sub.1-C.sub.6-alkoxy), 179
[0462] where the variables R.sup.1 to R.sup.7 have the meanings
stated under formula III and
[0463] L.sup.3 is C.sub.1-C.sub.6-alkoxy.
[0464] The especially preferred embodiments of the
3-(4,5-dihydroisoxazol-- 5-yl)carboxylic acid derivatives of the
formula III with regard to the variables R.sup.1 to R.sup.7
correspond to those of the
3-(4,5-dihydroisoxazol-5-yl)cyclohexenones of the formula I.
[0465] The 3-(4,5-dihydroisoxazol-5-yl)carbonyl halides of the
formula III.alpha.' (where L.sup.1'=Cl, Br,) can be prepared in a
conventional manner by reacting the
3-(4,5-dihydroisoxazol-5-yl)carboxylic acids of the formula
III.beta. with halogenating reagents such as thionyl chloride,
thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride
or oxalyl bromide.
[0466] The 3-(4,5-dihydroisoxazol-5-yl)carboxylic acids of the
formula III.beta. can be prepared in a conventional manner from the
corresponding esters of the formula III.gamma.
(L.sup.3=C.sub.1-C.sub.6-alkoxy) by means of acid or alkaline
hydrolysis. 180
[0467] Equally, the 3-(4,5-dihydroisoxazol-5-yl)carboxylic acids of
the formula III.beta. can be obtained by reacting corresponding
halogen-substituted compounds of the formula VI (L.sup.4=Hal), in
particular the iodine or bromine compounds, with carbon monoxide
and water under elevated pressure in the presence of a palladium,
nickel, cobalt or rhodium transition metal catalyst and a base.
181
[0468] Furthermore, it is possible to convert compounds of the
formula VI in a Rosenmund-von Braun reaction into the corresponding
nitriles of the formula VII (cf., for example, Org. Synth. Vol.
III, 212 (1955)) and to convert the latter into the compounds of
the formula III.beta. by subsequently hydrolyzing them.
[0469] The compounds of the formula VI or VII are also novel,
182
[0470] the variables having the following meanings:
[0471] R.sup.1, R.sup.2 are hydrogen, nitro, halogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio,
C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl,
C.sub.1-C.sub.6-alkylsulfonyl or
C.sub.1-C.sub.6-haloalkylsulfonyl;
[0472] R.sup.3 is hydrogen, halogen or C.sub.1-C.sub.6-alkyl;
[0473] R.sup.4 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0474] R.sup.5, R.sup.6 are hydrogen, halogen, cyano, nitro,
C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkoxy)-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alky- l)amino-C.sub.1-C.sub.4-alkyl,
di(C.sub.1-C.sub.4-alkyl)aminoimino-C.sub.1- -C.sub.4-alkyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-cyanoalkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, di(C.sub.1-C.sub.4-alkyl)amino,
COR.sup.8, phenyl or benzyl, it being possible for the two
last-mentioned substituents to be partially or fully halogenated
and/or to have attached to them one to three of the following
groups:
[0475] nitro, cyano, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.1-C.sub.4-haloalkoxy;
[0476] or
[0477] R.sup.5 and R.sup.6 together form a
C.sub.2-C.sub.6-alkanediyl chain which can be mono-to
tetrasubstituted by C.sub.1-C.sub.4-alkyl and/or can be interrupted
by oxygen or an unsubstituted or C.sub.1-C.sub.4-alkyl-substituted
nitrogen;
[0478] R.sup.7 is halogen, cyano, hydroxyl, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl,
C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-haloalkylsulfonyl, amino,
C.sub.1-C.sub.6-alkylamino, di(C.sub.1-C.sub.6-alkyl)amino,
di(C.sub.1-C.sub.4-alkoxy)methyl,
hydroxyimino-C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C- .sub.4-alkyl or
COR.sup.8;
[0479] R.sup.8 is hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalk- yl, hydroxyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub- .4-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-alkynyloxy or NR.sup.9R.sup.10;
[0480] R.sup.9 is hydrogen or C.sub.1-C.sub.4-alkyl;
[0481] R.sup.10 is C.sub.1-C.sub.4-alkyl; and
[0482] L.sup.4 is halogen.
[0483] The particular embodiments of the compounds of the formula
VI or VII with regard to the variables R.sup.1 to R.sup.7
correspond to those of the
3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the formula
I.
[0484] The esters of the formula III.gamma. or the halogen
compounds of the formula VI can be synthesized by subjecting
nitrile oxides and corresponding alkenes of the formula VIII or IX
to a 1,3-dipolar cycloaddition reaction. 183
[0485] The nitrile oxides are generated in situ in a conventional
manner. The starting materials used for this purpose are, for
example, aldoximes (cf., for example, Houben-Weyl X5, p. 858 et
seq.) or nitroalkanes (cf., for example, Houben-Weyl E5/2, p. 1594
et seq.). The synthesis of the compounds of the formula VIII or IX
is known (cf., for example, WO 98/50337 and WO 98/50366) or is
carried out in analogy to processes known from the literature.
PREPARATION EXAMPLES
[0486]
2-[2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylb-
enzoyl]-1-hydroxycyclohex-1-en-3-one
[0487] A solution of 2.3 g (7.7 mmol) of
2-methyl-3-(3-methyl-4,5-dihydroi-
soxazol-5-yl)-4-methylsulfonylbenzoyl chloride in 50 ml of
acetonitrile was added dropwise at 0-5.degree. C. to a solution of
0.86 g (7.7 mmol) of 1-hydroxycyclohex-1-en-3-one and 2.13 ml (15.4
mmol) of triethylamine in 50 ml of acetonitrile. After the mixture
had been stirred for three hours at room temperature, a further
0.64 ml (4.6 mmol) of triethylamine and 0.16 g (15 mmol) of
trimethylsilyl cyanide were added and the mixture was stirred for
twelve hours at room temperature. The reaction mixture was then
stirred into 800 ml of water and washed with methylene chloride.
The aqueous phase was then brought to pH 4 using 10% strength
hydrochloric acid and extracted with methylene chloride. After the
organic phase had been dried, the solvent was removed and the
residue was taken up in diethyl ether and digested. The resulting
residue was filtered off with suction. This gave 1.3 g (3.3 mmol;
43% of theory) of the title compounds.
[0488] M.p. 135-140.degree. C.
[0489] Tables 2 and 3 show not only the above compound, but also
further derivatives of the formula I which were, or can be,
prepared analogously.
2TABLE 2 I 184 where R.sup.3, R.sup.4 and R.sup.6 = H Physical data
No. R.sup.1 R.sup.2 R.sup.5 R.sup.7 R.sup.13 R.sup.14 R.sup.15
R.sup.16 R.sup.17 R.sup.18 m.p. [.degree. C.] 2.1 Cl Cl H
C(CH.sub.3).sub.3 H H H H H H 65-75 2.2 Cl SO.sub.2CH.sub.3 H
CO.sub.2CH.sub.2CH.sub.3 H H H H H H 154-158 2.3 Cl Cl H
CO.sub.2CH.sub.2CH.sub.3 H H H H H H 77-81 2.4 Cl Cl H CH.sub.3 H H
H H H H 84-94 2.5 CH.sub.3 SO.sub.2CH.sub.3 H CH.sub.3 H H H H H H
135-140 2.6 Cl SO.sub.2CH.sub.3 H CH.sub.3 H H H H H H 115-125 2.7
Cl Cl H CH.sub.3 CH.sub.3 CH.sub.3 .dbd.O CH.sub.3 CH.sub.3 82-85
2.8 Cl SO.sub.2CH.sub.3 H CH.sub.3 H H CH.sub.3 H H H 190-193 2.9
Cl SO.sub.2CH.sub.3 H CH.sub.3 H H CH.sub.3 CH.sub.3 H H 114-124
2.10 Cl SO.sub.2CH.sub.3 H CH.sub.3 H H H H CH.sub.3 CH.sub.3
164-168 2.11 Cl SO.sub.2CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3
.dbd.O CH.sub.3 CH.sub.3 103-105 2.12 CH.sub.3 SO.sub.2CH.sub.3 H
CH.sub.3 CH.sub.3 CH.sub.3 .dbd.O CH.sub.3 CH.sub.3 180-200 2.13
CH.sub.3 SO.sub.2CH.sub.3 H CH.sub.3 H H H H CH.sub.3 CH.sub.3
190-195 2.14 Cl Cl H CH.sub.3 H H CH.sub.3 H H H 81-84 2.15 Cl Cl H
CH.sub.3 H H CH.sub.3 CH.sub.3 H H 63-65 2.16 Cl Cl H CH.sub.3 H H
H H CH.sub.3 CH.sub.3 74-84 2.17 Cl Cl H CH.sub.3 CH.sub.3 H H H
CH.sub.3 H 80-85 2.18 Cl Cl H CH.sub.3 CH.sub.3 H H H CH.sub.3
CH.sub.3 80-85 2.19 OCH.sub.3 SO.sub.2CH.sub.3 H CH.sub.3 H H
CH.sub.3 CH.sub.3 H H 95-102 2.20 OCH.sub.3 SO.sub.2CH.sub.3 H
CH.sub.3 H H H H H H 175-185 2.21 CH.sub.3 SO.sub.2CH.sub.3 H
CH.sub.3 H H CH.sub.3 H H H 134-138 2.22 CH.sub.3 SO.sub.2CH.sub.3
H CH.sub.3 H H CH.sub.3 CH.sub.3 H H 183-186 2.23 OCH.sub.3
SO.sub.2CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.3 .dbd.O CH.sub.3
CH.sub.3 165-168 2.24 Cl Cl H COCH.sub.3 H H H H H H 73-78
[0490]
3TABLE 3 I 185 where R.sup.3, R.sup.4, R.sup.13, R.sup.15, R.sup.16
and R.sup.17 = H R.sup.14 + R.sup.18 = --CH.sub.2--CH.sub.2--
Physical data No. R.sup.1 R.sup.2 R.sup.5 R.sup.7 m.p. [.degree.
C.] 3.1 Cl SO.sub.2CH.sub.3 H CH.sub.3 107-108 3.2 CH.sub.3
SO.sub.2CH.sub.3 H CH.sub.3 190-122 3.3 Cl Cl H CH.sub.3 88-92 3.4
OCH.sub.3 SO.sub.2CH.sub.3 H CH.sub.3 88-106 3.5 Cl Cl H COCH.sub.3
88-95
[0491] The syntheses of some starting materials are shown
hereinbelow:
[0492] Methyl
2,4-dichloro-3-(3-t-butyl-4,5-dihydroisoxazol-5-yl)benzoate
[0493] 17 ml of a 12% strength aqueous sodium hypochlorite solution
were added dropwise at room temperature into a vigorously stirred
solution of 2.6 g (10 mmol) of methyl
2,4-dichloro-3-ethenylbenzoate and 1 g (10 mmol) of
2,2-dimethylpropional-doxime in 100 ml of dichloromethane. After
the mixture had been stirred for in each case 2 hours, two further
portions of 0.5 g (5 mmol) of the oxime and 9 ml of the
hypochlorite solution were added. Stirring was continued for 12
hours at room temperature, and the reaction mixture was then
stirred into 350 ml of water. After extraction with
dichloromethane, drying and removal of the solvent, the residue was
chromatographed.
[0494] Yield: 1.5 g (45% of theory) of yellow resin
[0495] Methyl
2-chloro-3-(3-ethoxycarbonyl-4,5-dihydroisoxazol-5-yl)-4-met-
hylsulfonylbenzoate.
[0496] 6.4 ml (46 mmol) of triethylamine were added slowly dropwise
at room temperature to a solution of 8.5 g (31 mmol) of methyl
2-chloro-3-ethenyl-4-methylsulfonylbenzoate and 7.2 g (46 mmol) of
ethyl 2-chloro-2-hydroxyiminoacetate in 200 ml of dichloromethane.
After the mixture had been stirred for in each case 2 hours, 3
further portions of in each case 4.8 g (31 mmol) of ethyl
2-chloro-2-hydroxyiminoacetate and then 4.3 ml (31 mmol) of
triethylamine were added. Stirring was continued for 12 hours at
room temperature, and the reaction mixture was then stirred into
600 ml of water. After extraction with dichloromethane, drying and
removal of the solvent, the residue was chromatographed.
[0497] Yield: 5.7 g (47% of theory) of clear resin.
[0498]
2-Chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenz-
oic acid
[0499] a) Methyl
2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsu-
lfonylbenzoate.
[0500] One spatula-tip full of 4-dimethylaminopyridine was added to
a solution of 40 g (145 mmol) of methyl
2-chloro-3-ethenyl-4-methylsulfonyl- benzoate and 50 g (220 mmol)
of di-t-butyl dicarbonate in 300 ml of acetonitrile, and 50 g (640
mmol) of nitroethane were then added dropwise. After the mixture
had been stirred for 12 hours at room temperature, a further 32.8 g
(145 mmol) of di-t-butyl dicarbonate and 22.9 g (290 mmol) of
nitroethane were added. After a further 12 hours, the solvent was
distilled off and the residue was digested with ethyl acetate.
Following filtration with suction, 32.1 g of the desired compound
remained. A further 6.3 g were obtained from the mother liquor
after removal of the solvent followed by chromatography.
[0501] Yield: 39.4 g (82% of theory)
[0502] M.p.: 175.degree. C.
[0503] b) Methyl
2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsu-
lfonylbenzoic acid
[0504] 69.4 g (174 mmol) of 10% strength sodium hydroxide solution
were added to a solution of 38.4 g (116 mmol) of methyl
2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoate
in 400 ml of methanol and 400 ml of tetrahydrofuran. The mixture
was stirred for 12 hours at room temperature, the solvent volume
was reduced to half, and the mixture was poured into 1 l of water.
The pH was brought to 1 using 10% strength hydrochloric acid, and
the precipitate which formed was filtered off with suction.
[0505] Yield: 35.2 g (96% of theory)
[0506] M.p.: >220.degree. C.
[0507]
2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenz-
oic acid
[0508] a)
2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)methylsulfonylbenz-
oic acid
[0509] One spatula-tip full of 4-dimethylaminopyridine was added to
a solution of 13.6 g (50 mmol) of
2-methyl-3-ethenyl-4-methylsulfonylbromob- enzene and 16.7 g (74
mmol) of di-t-butyl dicarbonate in 100 ml of acetonitrile, and 17.9
g (229 mmol) of nitroethane were then slowly added dropwise. After
the mixture had been stirred for 6 hours at room temperature, a
further 11.1 g (50 mmol) of di-t-butyl dicarbonate and 7.8 g (100
mmol) of nitroethane were added and the mixture was stirred for 12
hours at room temperature.
[0510] After the solvent had been removed, the residue was
chromatographed.
[0511] Yield: 6.4 g (38% of theory)
[0512] b)
2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylb-
enzoic acid
[0513] 6.4 g (19 mmol) of
2-methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-
-methylsulfonylbromobenzene were dissolved in 65 ml of toluene and
30 ml of water and treated with 240 mg (1 mmol) of palladium
acetate, 1.1 g (4 mmol) of tricyclohexylphosphane, 810 mg (19 mmol)
of lithium chloride and 5.4 ml (38 mmol) of triethylamine. The
resulting solution was then stirred in an autoclave for 36 hours at
140.degree. C. under a carbon monoxide pressure of 20 bar. After
cooling the autoclave and releasing the pressure, insoluble
constituents were removed by filtration, and the phases were
separated. The organic phase was subsequently extracted twice with
water containing a little triethylamine. The combined aqueous
phases were then brought to pH 1 using 10% hydrochloric acid, and
the precipitate which formed was filtered off.
[0514] Yield: 2.5 g (44% of theory)
[0515] M.p.: 199-205.degree. C.
[0516] Table 4 which follows lists not only the above-described
compounds, but also further 3-(4,5-dihydroisoxazol-5-yl)carboxylic
acid derivatives of the formula III which are prepared, or can be
prepared, analogously.
4TABLE 4 I 186 where R.sup.4 and R.sup.6 = H Physical data No.
R.sup.1 R.sup.2 R.sup.3 R.sup.5 R.sup.7 R.sup.15 [.degree. C.] 4.1
Cl Cl H H CH.sub.3 OCH.sub.3 Resin 4.2 Cl Cl H H CH.sub.3 OH Resin
4.3 Cl Cl H H C(CH.sub.3).sub.3 OCH.sub.3 Resin 4.4 Cl Cl H H
C(CH.sub.3).sub.3 OH 4.5 Cl SO.sub.2CH.sub.3 H H C(CH.sub.3).sub.3
OCH.sub.3 54-55 4.6 Cl SO.sub.2CH.sub.3 H H C(CH.sub.3).sub.3 OH
97-100 4.7 Cl Cl H H COOEt OCH.sub.3 Oil 4.8 Cl Cl H H COOEt OH 4.9
Cl SO.sub.2CH.sub.3 H H COOEt OCH.sub.3 Resin 4.10 Cl
SO.sub.2CH.sub.3 H H COOEt OH 82-90 4.11 Cl Cl H H COOH OH 182-183
4.12 Cl Cl H H CF.sub.3 OCH.sub.3 Oil 4.13 Cl Cl H H CF.sub.3 OH
4.14 Cl SO.sub.2CH.sub.3 H H CH.sub.3 OCH.sub.3 175 4.15 Cl
SO.sub.2CH.sub.3 H H CH.sub.3 OH >220 4.16 CH.sub.3
SO.sub.2CH.sub.3 H H CH.sub.3 OCH.sub.3 120-121 4.17 CH.sub.3
SO.sub.2CH.sub.3 H H CH.sub.3 OH 199-205 4.18 Cl SO.sub.2CH.sub.3 H
H CH(OC.sub.2H.sub.5).sub.2 OCH.sub.3 Resin 4.19 Cl
SO.sub.2CH.sub.3 H H CH(OC.sub.2H.sub.5).sub.2 OH 4.20 Cl
SO.sub.2CH.sub.3 H H CHO OCH.sub.3 4.21 Cl SO.sub.2CH.sub.3 H H CHO
OH 4.22 Cl Cl H CH.sub.3 C(CH.sub.3).sub.3 OCH.sub.3 4.23 Cl Cl H
CH.sub.3 C(CH.sub.3).sub.3 OH 4.24 Cl Cl H H COCH.sub.3 OCH.sub.3
4.25 Cl Cl H H COCH.sub.3 OH 4.26 Cl Cl H H Cl OCH.sub.3 4.27 Cl Cl
H H Cl OH
[0517] The 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of the
formula I and their agriculturally useful salts, both in the form
of the isomer mixtures and in the form of the pure isomers, are
suitable as herbicides. The herbicidal compositions comprising
compounds of the formula I effect very good control of vegetation
on non-crop 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 damaging the crop plants
significantly. This effect is observed especially at low
application rates.
[0518] Depending on the application method in question, the
compounds of the formula I or herbicidal compositions comprising
them can additionally be employed in a further number of crop
plants for eliminating undesired plants. Examples of suitable crop
plants are:
[0519] 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.
[0520] Moreover, the compunds of the formula I can also be used in
crops which tolerate the action of herbicides due to breeding,
including recombinant methods.
[0521] The compounds of the formula I, or the herbicidal
compositions comprising them, can be employed, 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, or as a seed treatment or by mixing
with the seed. 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.
[0522] The herbicidal compositions comprise a herbicidally active
amount of at least one compound of the formula I or of an
agriculturally useful salt of I and adjuvants conventionally used
for the formulation of crop protection products.
[0523] Suitable inert auxiliaries are essentially: mineral oil
fractions of medium to high boiling point such as kerosene and
diesel oil, furthermore coal tar oils and oils of vegetable or
animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
paraffins, tetrahydronaphthalene, alkylated naphthalenes and their
derivatives, alkylated benzenes and their derivatives, alcohols
such as methanol, ethanol, propanol, butanol and cyclohexanol,
ketones such as cyclohexanone, strongly polar solvents, e.g. amines
such as N-methylpyrrolidone, and water.
[0524] Aqueous use forms can be prepared from emulsion
concentrates, suspensions, pastes, wettable powders or
water-dispersable granules by adding water. To prepare emulsions,
pastes or oil dispersions, the
3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones, as such or
dissolved in an oil or solvent, can be homogenized in water by
means of wetters, tackifiers, dispersants or emulsifiers. However,
it is also possible to prepare concentrates composed of active
substance, wetter, tackifier, dispersant or emulsifier and, if
appropriate, solvent or oil which are suitable for dilution with
water.
[0525] Suitable surfactants (adjuvants) are the alkali metal salts,
alkaline earth metal salts and ammonium salts of aromatic sulfonic
acids, e.g. ligno-, phenol-, naphthalene-and
dibutylnaphthalenesulfonic acid, and of fatty acids, of alkyl- and
alkylarylsulfonates, of alkyl sulfates, lauryl ether sulfates and
fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and
octadecanols, and of fatty alcohol glycol ether, condensates of
sulfonated naphthalene and its derivatives with formaldehyde,
condensates of naphthalene, or of the naphthalenesulfonic acids,
with phenol and formaldehyde, polyoxyethylene octylphenol ether,
ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenyl and
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.
[0526] Powders, materials for spreading and dusts can be prepared
by mixing or concomitantly grinding the active substances with a
solid carrier.
[0527] Granules, for example 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.
[0528] The concentrations of the compounds of the formula I in the
ready-to-use products can be varied within wide ranges. In general,
the formulations comprise approximately from 0.001 to 98% by
weight, preferably 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% (according to NMR
spectrum).
[0529] The formulation examples below illustrate the preparation of
such products:
[0530] I. 20 parts by weight of the compound No. 2.5 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
and 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 and 1 mol of castor oil. Pouring the
solution into 100000 parts by weight of water and finely
distributing it therein gives an aqueous dispersion which comprises
0.02% by weight of the active ingredient.
[0531] II. 20 parts by weight of the compound No. 2.9 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 and 1 mol of isooctylphenol and 10 parts by
weight of the adduct of 40 mol of ethylene oxide and 1 mol of
castor oil. Pouring the solution into 100000 parts by weight of
water and finely distributing it therein gives an aqueous
dispersion which comprises 0.02% by weight of the active
ingredient.
[0532] III. 20 parts by weight of the active ingredient No. 2.5 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.degree. 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 100000 parts by weight of water and finely
distributing it therein gives an aqueous dispersion which comprises
0.02% by weight of the active ingredient.
[0533] IV. 20 parts by weight of the active ingredient No. 2.9 are
mixed thoroughly with 3 parts by weight of sodium
diisobutylnaphthalenesulfonat- e, 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 20000
parts by weight of water gives a spray mixture which comprises 0.1%
by weight of the active ingredient.
[0534] V. 3 parts by weight of the active ingredient No. 2.5 are
mixed with 97 parts by weight of finely divided kaolin. This gives
a dust which comprises 3% by weight of the active ingredient.
[0535] VI. 20 parts by weight of the active ingredient No. 2.9 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.
[0536] VII. 1 part by weight of the active ingredient No. 2.5 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.
[0537] VIII,. 1 part by weight of the active ingredient No. 2.4 is
dissolved in a mixture composed of 80 parts by weight of
cyclohexanone and 20 parts by weight of Wettol.RTM. EM 31
(=nonionic emulsifier based on ethoxylated castor oil). This gives
a stable emulsion concentrate.
[0538] The compounds of the formula I or the herbicidal
compositions can be applied pre-emergence, post-emergence or
together with the seed of a crop plant. It is also possible to
apply the compounds of the formula I or the herbicidal compositions
by sowing the seed, of a crop plant, which has been pretreated with
the herbicidal compositions or active ingredients. 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 into very little contact, if any, with
the leaves of the sensitive crop plants, while the active
ingredients reach the leaves of undesired plants growing
underneath, or the naked soil surface (post-directed, lay-by).
[0539] Depending on the intended aim of the control measures, the
season, the target plants and the growth stage, the application
rates of compound of the formula I are from 0.001 to 3.0,
preferably from 0.01 to 1.0, kg of active substance (a.s.) per
ha.
[0540] To widen the spectrum of action and to achieve synergistic
effects, the 3-(4,5-dihydroisoxazol-5-yl)benzoylcyclohexenones of
the formula I can be mixed with a large number of representatives
of other groups of active ingredients which act as herbicides or as
growth regulators and applied together with these. Suitable
components in 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-(hetaroyl/aroyl)-1,3-cyclohex- anediones, heteroaryl aryl
ketones, benzylisoxazolidinones, meta-CF.sub.3-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
derivatives, phenylpropionic acid and its derivatives, pyrazoles,
phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its
derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas,
triazines, triazinones, triazolinones, triazolecarboxamides and
uracils.
[0541] Moreover, it may be advantageous to apply the compounds of
the formula I, alone or in combination with other herbicides, or in
the form of a mixture with other crop protection agents, for
example with agents for controlling pests or phytopathogenic fungi
or bacteria. Also of interest is the miscibility with mineral salt
solutions, which are employed for treating nutritional and trace
element deficiencies. Nonphytotoxic oils and oil concentrates can
also be added.
[0542] Use Examples
[0543] The herbicidal action of the
3-(4,5-dihydroisoxazol-5-yl)benzoylcyc- lohexenones of the formula
I was demonstrated by the following greenhouse experiments:
[0544] The culture containers used were plastic flower pots
containing loamy sand with approximately 3.0% of humus as
substrate. The seeds of the test plant were sown separately for
each species.
[0545] For the pre-emergence treatment, the active ingredients,
which were suspended or emulsified in water, were applied directly
after sowing by means of finely distributing nozzles. The
containers were irrigated gently to promote germination and growth
and subsequently covered with transparent plastic hoods until the
plants had rooted. This cover caused uniform germination of the
test plants unless this was adversely affected by the active
ingredients.
[0546] 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. To this end, the test plants
were either sown directly and grown in the same containers, or they
were first grown separately as seedlings and transplanted into the
test containers a few days prior to the treatment. The rate of
application for the post-emergence the treatment was 125 or 62.5 g
of a.s. (active substance) per ha.
[0547] Depending on the species, the plants were kept at
temperatures of from 10 to 25.degree. C. or from 20 to 35.degree.
C. The test period extended over 2 to 4 weeks. During this time,
the plants were tended, and their response to the individual
treatments was evaluated.
[0548] Evaluation was carried out using a scale of from 0 to 100.
100 means no emergence of the plants, or complete destruction of at
least the aerial parts, and 0 means no damage or normal course of
growth.
[0549] The plants used in the greenhouse experiments belonged to
the following species:
5 Scientific name Common name Amaranthus retroflexus redroot
pigweed Chenopodium album lambsquarters (goosefoot) Digitaria
sanguinalis hairy fingergrass Panicum dichotomiflorum fall panicum
Polygonum persicaria ladysthumb Solanum nigrum black nightshade
Stellaria media common chickweed Matricaria false chamomile
Brachiaria platyphylla broadleaf signal grass Lamium amplexicaule
henbit
[0550] When rates of application of 125 or 62.5 g/ha a.s. were
employed, the compound 2.4 was very effective against Brachiaria
platyphylla, lambsquarters, Lamium amplexicaule, chamomile and
common chickweed. Equally, the compound 2.9 controlled redroot
pigweed, lambsquarters, hairy fingergrass, ladysthumb and fall
panicum very efficiently under analogous conditions. Used
pre-emergence at application rates of 125 or 62.5 g/ha, the
compound 2.5 controls redroot pigweed, hairy fingergrass,
lambsquarters and black nightshade highly efficiently.
* * * * *