Cyclohexadiene-derivatives as pesticides

Details Cyclohexadiene-derivatives as pesticides Cyclohexadiene-derivatives as pesticides

2000-06-01

2001-10-30

Shah, Mukund J. (Department: 7624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C560S035000

Reexamination Certificate

active

06310096

ABSTRACT:

The invention relates to novel pesticidally active compounds of the formula I
wherein:
X is CH or N;
Y is O; S, S═O or NR
5
;
Z is OR
2
, SR
2
, N(R
3
)R
4
; or
Y and Z together form a 5- to 7-membered ring which contains 2 or 3 hetero atoms O and/or N and which is unsubstituted or substituted by C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, halogen, ═O or cyclopropyl;
V is a direct bond or a 1 to 12 membered, saturated or unsaturated carbon chain which is unsubstituted or substituted by C
1
-C
3
alkyl, C
2
-C
3
alkylidene, C
3
-C
6
cycloalkylidene, halogen, hydroxy, C
1
-C
4
alkoxy, halo-C
1
-C
4
alkoxy or oxo;
W is hydrogen or substituted or unsubstituted aryl or substituted or unsubstituted hetaryl or trialkylsilyl;
R
1
is cyclopropyl, C
1
-C
6
alkyl or halo-C
1
-C
6
alkyl;
R
2
and R
3
independently of one another are C
1
-C
6
alkyl or halo-C
1
-C
6
alkyl;
R
4
and R
5
independently of one another are hydrogen, C
1
-C
6
alkyl or C
1
-C
6
alkoxy;
R
21
and R
22
independently of one another are hydrogen, halogen, C
1
-C
8
alkyl or C
1
-C
8
alkoxy or C
1
-C
8
alkylthio;
R
23
, R
24
, R
25
, R
26
independently of one another are hydrogen, halogen, C
1
-C
8
alkyl or C
1
-C
8
alkoxy.
The formula I embraces all stereoisomeric forms and mixtures of these, such as racemic and diasteromeric mixtures, for example E/Z mixtures. The compounds according to the invention have fungicidal, acaricidal and insecticidal properties and are suitable as active ingredients for use in agriculture, in horticulture and in the hygiene sector. The invention furthermore relates to the preparation of these compounds, to agrochemical compositions which comprise, as active ingredients, at least one of these compounds, and to the use of the active ingredients or of the compositions for protecting plants against attack by harmful microorganisms, and for controlling insects.
2-Alkoximino-2-phenylacetic acid derivatives and 2-alkoxymethylene-2-phenylacetic acid derivatives as pesticides are disclosed, for example, in EP-A-253 213 and EP-A-178 826. Corresponding pesticide compounds which have a cyclohexenyl group instead of the phenyl group are described in EP-A-421 102, those in which the phenyl group is replaced by a cyclohexyl group in EP-A-438 726. The phytofungicidal activity of 1,4-cyclohexadiene-1-alanine is furthermore described in J. of Antibiotics, Vol. XXIII, No. 11, pp.537-541 (1970).
The general terms used hereinabove and hereinbelow have the meanings given hereafter, unless otherwise defined:
Aryl is phenyl, naphthyl, phenanthryl or fluorenyl, in particular phenyl. Hetaryl are 5- or 6-membered aromatic rings which have hetero atoms N, O and/or S, and which can be benzo-fused. Examples are furane, pyrrole, pyridine, pyrimidine, pyrazine, thiazole, oxazole, isoxazole, isothiazole, triazine, quinoline, isoquinoline, pyridazine, pyrazole, imidazole, quinazoline, quinoxaline, benzimidazole, benzofuran, indole, isoindole, benzothiazole, benzoxazole. Heterocyclyl denotes 5- to 7-membered non-aromatic rings which contain 1-3 identical or different hetero atoms N, O, S. Examples are &Dgr;
2
-oxazoline, &Dgr;
2
-thiazoline; 5,6-dihydro-4H-1 ,3-thiazine; 5,6-dihydro-4H-1 ,3-oxazine, pyrrolidine, indoline, piperidine, morpholine, 4-alkylpiperidine, azepine. Alkyl groups are straight-chain or branched, depending on the number of the carbon atoms, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, sec-amyl, tert-amyl, 1-hexyl or 3-hexyl.
Unsaturated hydrocarbon radicals are alkenyl, alkynyl or alkenynyl groups having not more than 3 multiple bonds, for example butadienyl, hexatrienyl, 2-penten4-ynyl. Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. Preferred alkenyl radicals are those which have a chain length of 3 to 4 carbon atoms. Alkynyl can also be straight-chain or branched, depending on the number of the carbon atoms, for example ethynyl, propargyl, but-1-yn-1-yl, but-1-yn-3-yl. Propargyl is preferred. Saturated or unsaturated carbon chains as bridging elements are for example alkylene, alkylidene, alkenylene, and alkynylene, as methylene, ethylene, propylene, vinylene, propenylene, methylidyne, ethylidene, butanediylidyne. Halogen or halo are fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Haloalkyl can contain identical or different halogen atoms, for example fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3,3,3,-trifluoropropyl.
Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, iso-butyloxy, sec-butyloxy and tert-butyloxy; preferably methoxy and ethoxy. Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2- tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy. Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Alkanoyl is either straight-chain or branched; examples are formyl, acetyl, propionyl, butyryl, pivaloyl or octanoyl. All the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkoxy and alkanoyl groups mentioned hereinabove and hereinbelow can be substituted by aryl, hetaryl, aryloxy, hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, heterarylsulfenyl, hetarylsulfinyl or heterarylsulfonyl, each of which is unsubstiuted or additionally substituted. All the aryl and hetaryl groups mentioned hereinabove and hereinbelow can be mono- or polysubstituted, for example by halogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
-haloalkynyl, C
1
-C
4
haloalkoxy, halogen, cyano, cyano-C
1
-C
2
alkyl, cyano-C
1
-C
2
alkoxy, OH, NO
2
, SCN, thiocyanomethyl, Si(CH
3
)
3
, NH
2
, NH(C
1
-C
4
alkyl), N(C
1
-C
4
alkyl)
2
, C
1
-C
4
alkoxymethyl, C
1
-C
4
haloalkylcarbonyl, C
1
-C
4
haloalkyloxycarbonyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, aminocarbonyl, C
1
-C
4
alkylaminocarbonyl, bis(C
1
-C
4
alkylamino)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C
1
-C
4
alkoximinomethyl, —CSNH
2
, —SH, C
1
-C
4
alkylthiomethyl, C
2
-C
4
alkenyloxy, C
2
-C
4
alkynyloxy, C
2
-C
4
haloalkenyloxy, C
1
-C
4
alkylsulfinylmethyl, C
1
-C
4
alkylsulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C
3
-C
6
cycloalkyl, C
1
-C
4
haloalkylcarbonyloxy, C
1
-C
4
alkylcarbonyloxy, C
1
-C
4
alkoxycarbonyloxy, haloalkoxycarbonyloxy, aminocarbonyloxy, C
1
-C
4
alkylaminocarbonyloxy, bis(C
1
-C
4
alkylamino)carbonyloxy, arylaminocarbonyloxy, arylaminothiocarbonyioxy. All the abovementioned enumerations are by way of example and not by limitation.
Preferred are the following groups:
(1) Compounds of the formula I in which:
W is hydrogen or C
1
-C
6
alkyl or a group a)
in which
D are identical or different substituents halogen, cyano, nitro, C
1
-C
12
alkyl, halo-C
1
-C
6
alkyl, C
2
-C
12
alkenyl, halo-C
2
-C
12
alkenyl, C
2
-C
12
alkynyl, halo-C
2
-C
12
alkynyl, free or halogenated C
3
-C
6
cycloalkyl, free or halogenated C
3
-C
6
cycloalkylmethyl, free or halogenated C
3
-C
6
cycloalkylmethyloxy, C
1
-C
4
alkoxy, halo-C
1
-C
4
alkoxy, C
2
-C
6
alkenyloxy, halo-C
2
-C
6
alkenyloxy, C
2
-C
6
alkynyloxy, halo-C
2
-C
6
alkynyloxy, C
2
-C
12
alkoxyalkyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
6
alkylcarbonyl, it being possible for all the abovementioned alkyl, alkenyl or alkynyl groups to be substituted by aryl or hetaryl, aryloxy or hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, hetarylsulfenyl, hetarylsulfinyl or hetarylsulfonyl radicals, each of which can be additionally substituted or unsubstituted; furthermore substituted or unsubstituted aryl, substituted or unsubstituted hetaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxy, substituted or unsubstituted benzyl, substituted or unsubstituted cyclohexenyl,

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