Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-12-10
2001-09-11
Oswecki, Jane C. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S270000, C514S274000, C514S307000, C514S317000, C514S327000, C514S329000, C514S330000, C514S331000, C514S341000, C514S355000, C514S357000, C514S364000, C514S365000, C514S369000, C514S378000, C514S383000, C514S386000, C514S389000, C514S419000, C514S452000, C514S456000, C514S463000, C514S464000, C514S465000, C514S466000, C514S472000, C514S436000, C514S532000, C514S534000, C514S538000, C514S613000, C514S617000, C514S618000, C514S620000, C514S640000, C544S299000, C544S301000, C544S302000, C544S315000, C544S
Reexamination Certificate
active
06288071
ABSTRACT:
The invention relates to novel pesticidally active compounds of formula I
wherein:
X is CH or N;
Y is O, S, S═O or NR
5
;
Z is OR
2
, SR
2
or N(R
3
)R
4
;
n is 0, 1, 2, 3, 4 or 5; or
Y and Z together form a 5- to 7-membered ring containing 2 or 3 hetero atoms O and/or N that is unsubstituted or mono- or poly-substituted by C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, halogen, ═O or by cyclopropyl;
W is an aldimino or ketimino group;
R
1
is cyclopropyl, C
1
-C
6
alkyl or halo-C
1
-C
6
-alkyl;
R
2
and R
3
are each independently of the other C
1
-C
6
alkyl or halo-C
1
-C
6
alkyl;
R
4
and R
5
are each independently of the other hydrogen, C
1
-C
6
alkyl or C
1
-C
6
alkoxy;
R
8
and R
9
are each independently of the other hydrogen or C
1
-C
3
alkyl; or
R
8
and R
9
together are C
2
-C
6
alkenyl or C
3
-C
6
cycloalkyl;
R
21
and R
22
are each independently of the other hydrogen, halogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy or C
1
-C
8
alkylthio; and
R
23
, R
24
, R
25
and R
26
are each independently of the others hydrogen, halogen, C
1
-C
8
alkyl or C
1
-C
8
alkoxy.
Formula I includes all stereoisomeric forms and also mixtures thereof, such as racemic and diastereoisomeric mixtures, for example E/Z mixtures.
The compounds of the invention have fungicidal, acaricidal and insecticidal properties and are suitable for use as active ingredients in agriculture, horticulture and in the hygiene sector.
The invention relates also to the preparation of those compounds, to agrochemical compositions that comprise at least one of those compounds as active ingredient, and to the use of the active ingredients or compositions in the protection of plants against attack by harmful microorganisms as well as in the control of insects.
2-Alkoximino-2-phenylacetic acid derivatives and 2-alkoxymethylene-2-phenylacetic acid derivatives are known as pesticides, for example, from WO 94/26700 and WO 95/18789. Corresponding pesticidal compounds in which a cyclohexenyl group stands in place of the phenyl group are described in EP-A-421 102, and those in which the phenyl group has been replaced by a cyclohexyl group are described in EP-A-438 726. In addition, the phytofungicidal action of 1,4-cyclohexadiene-1-alanine is described in J. of Antibiotics, Vol. XXIII, No.11, p. 537-541 (1970).
The general terms used hereinbefore and hereinafter have the meanings given below unless specified otherwise:
Hydrocarbon radicals may be saturated or unsaturated, open-chained or cyclic, or a mixture of open-chained and cyclic such as, for example, cyclopropylmethyl or benzyl.
Alkyl groups are straight-chain or branched, depending on the number of carbon atoms, and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, sec-amyl, tert-amyl, 1-hexyl or 3-hexyl.
Unsaturated hydrocarbon radicals are alkenyl, alkynyl or alkenynyl groups having a maximum of 3 multiple bonds, such as, for example, butadienyl, hexatrienyl or 2-penten-4-ynyl.
Alkenyl is to be understood as meaning straight-chain or branched alkenyl, such as, for example, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. Alkenyl radicals having a chain length of 3 or 4 carbon atoms are preferred.
Alkynyl may similarly, depending on the number of carbon atoms, be straight-chain or branched, such as, for example, ethynyl, propargyl, but-1-yn-1-yl or but-1-yn-3-yl. Propargyl is preferred.
Cyclic unsaturated hydrocarbon radicals may be aromatic, such as, for example, phenyl and naphthyl, or non-aromatic, such as, for example, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctadienyl, or partially aromatic, such as, for example, tetrahydronaphthyl and indanyl.
Halogen and halo are fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Haloalkyl may contain identical or different halogen atoms and may be, for example, fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl or 3,3,3-trifluoropropyl.
Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy; preferably methoxy or ethoxy.
Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2-difluoroethoxy.
Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Alkanoyl is either straight-chain or branched. Examples are formyl, acetyl, propionyl, butyryl, pivaloyl and octanoyl.
Aryl is phenyl or naphthyl, preferably phenyl.
The term heteroaryl denotes 5- or 6-membered aromatic rings containing hetero atoms N, O and/or S, which may be benzo-fused. Examples are furan, pyrrole, pyridine, pyrimidine, pyrazine, thiazole, oxazole, isoxazole, isothiazole, triazine, quinoline, isoquinoline, pyridazine, pyrazole, imidazole, quinazoline, quinoxaline, benzimidazole, benzofuran, indole, isoindole, benzothiazole and benzoxazole.
Heterocyclyl denotes 5- to 7-membered, non-aromatic rings that contain from 1 to 3 identical or different hetero atoms N, O and 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 and azepine.
All of the above lists are given by way of example and are not limiting in any way.
The following groups are preferred:
(1) Compounds of formula I wherein:
W is a group a)
wherein
R
11
and R
12
are each independently of the other hydrogen, cyano, C
1
-C
12
alkyl, halo-C
1
-C
12
-alkyl, C
2
-C
12
alkenyl, C
2
-C
12
alkynyl, C
3
-C
6
cycloalkyl, cyclopropylmethyl, C
1
-C
4
alkoxy, C
2
-C
12
-alkoxyalkyl, C
1
-C
4
alkoxycarbonyl, aminocarbonyl, C
1
-C
4
alkylaminocarbonyl, bis(C
1
-C
4
alkyl)-aminocarbonyl, ureidocarbonyl, C
1
-C
4
alkylthio, C
2
-C
5
alkylthioalkyl; an unsubstituted or up to penta-substituted ring having a maximum of 15 ring carbon atoms that may be multi-membered and contains from 0 to 3 hetero atoms N, O and/or S, it being possible for the ring to be bonded by a bridge having a maximum of 4 chain atoms and that may be linear or branched and may contain CO, oxygen or sulfur; or
R
11
and R
12
together with the common carbon atom are an unsubstituted or up to penta-substituted ring having a maximum of 15 ring carbon atoms that may be multi-membered and contains from 0 to 3 hetero atoms N, O and/or S;
the possible substituents of all of those groups mentioned for R
11
and R
12
individually or together being selected from C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
alkoxy, C
1
-C
4
alkyl-thio, 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, oxo, thioxo, 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
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
haloalkylcarbonyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
haloalkoxycarbonyl, aminocarbonyl, C
1
-C
4
alkylaminocarbonyl, bis(C
1
-C
4
alkylamino)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C
1
-C
4
haloalkylcarbonyloxy, C
1
-C
4
alkylcarbonyloxy, C
1
-C
4
alkoxycarbonyloxy, aminocarbonyloxy, C
1
-C
4
alkylaminocarbonyloxy, bis(C
1
-C
4
alkylamino)carbonyloxy, arylaminocarbonyloxy, arylaminothiocarbonyloxy, 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, phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio;
it being possible for the aromatic groups to carry a maximum of five further substituents selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy, CN and NO
2
, and it being possible for two adjacent substituents of the maximum of 5 substituents to form an aliphatic bridge having a maximum of 5 members, which br
Huter Ottmar Franz
Szczepanski Henry
Zeller Martin
Bayer Aktiengesellschaft
Gil Joseph C.
Oswecki Jane C.
Zurcher Jackie Ann
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