Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-09-16
2004-03-16
Pryor, Alton N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06706758
ABSTRACT:
The present invention relates to novel active compound combinations comprising known cyclic ketoenols on the one hand and other known insecticidally active compounds on the other hand and which are highly suitable for controlling animal pests such as insects and undesired acarids.
It is already known that certain cyclic ketoenols have insecticidal and acaricidal properties (EP-A-528 156). Further ketoenols having insecticidal and acaricidal properties are described in WO 95/01971, EP-A-647 637, WO 96/16061, WO 96/20196, WO 96/25395, WO 96/35664, WO 97/02243, WO 97/01535, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 99/16748, WO 99/43649, WO 99/48869 and WO 99/55673. The activity of these substances is good; however, at low application rates it is sometimes unsatisfactory.
Furthermore, it is already known that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf. WO 93-22 297, WO 93-10 083, DE-A 2 641 343, EP-A-347 488, EP-A-210 487, U.S. Pat. No. 3,264,177 and EP-A-234 045). However, the activity of these substances is not always satisfactory.
It has now been found that compounds of the formula (I)
in which
X represents C
1
-C
6
-alkyl, halogen, C
1
-C
6
-alkoxy or C
1
-C
3
-halogenoalkyl,
Y represents hydrogen, C
1
-C
6
-alkyl, halogen, C
1
-C
6
-alkoxy or C
1
-C
3
-halogenoalkyl,
Z represents C
1
-C
6
-alkyl, halogen or C
1
-C
6
-alkoxy,
n represents a number from 0 to 3,
A represents hydrogen or in each case optionally halogen-substituted straight-chain or branched C
1
-C
12
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-alkinyl, C
1
-C
10
-alkoxy-C
2
-C
8
-alkyl, C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl, C
1
-C
10
-alkylthio-C
2
-C
8
-alkyl or cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur and represents in each case optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-halogenoalkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkoxy- or nitro-substituted phenyl or phenyl-C
1
-C
6
-alkyl,
B represents hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy-C
2
-C
4
-alkyl
or in which
A and B together with the carbon atom to which they are attached form a saturated or unsaturated 3- to 8-membered ring which is optionally interrupted by oxygen and/or sulphur and optionally substituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-alkylthio or optionally substituted phenyl or is optionally benzo-fused,
G represents hydrogen (a) or represents a group
in which
R
1
represents in each case optionally halogen-substituted C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl, C
1
-C
8
-alkoxy-C
2
-C
8
-alkyl, C
1
-C
8
-alkylthio-C
2
-C
8
-alkyl, C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl or cycloalkyl having 3-8 ring atoms which may be interrupted by oxygen and/or sulphur atoms,
represents optionally halogen-, nitro-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-halogenoalkoxy-substituted phenyl,
represents optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-halogenoalkoxy-substituted phenyl-C
1
-C
6
-alkyl,
represents in each case optionally halogen- and/or C
1
-C
6
-alkyl-substituted pyridyl, pyrimidyl, thiazolyl or pyrazolyl,
represents optionally halogen- and/or C
1
-C
6
-alkyl-substituted phenoxy-C
1
-C
6
-alkyl,
R
2
represents in each case optionally halogen-substituted C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl, C
1
-C
8
-alkoxy-C
2
-C
8
-alkyl or C
1
-C
8
-polyalkoxy-C
2
-C
8
-alkyl,
represents in each case optionally halogen-, nitro-, C
1
-C
6
-alkyl-, C
1
-C
6
-alkoxy- or C
1
-C
6
-halogenoalkyl-substituted phenyl or benzyl,
R
3
represents optionally halogen-substituted C
1
-C
8
-alkyl, represents in each case optionally C
1
-C
4
-alkyl-, halogen-, C
1
-C
4
-halogenoalkyl-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, nitro- or cyano-substituted phenyl or benzyl,
R
4
and R
5
independently of one another represent in each case optionally halogen-substituted C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-alkylamino, di-(C
1
-C
8
)-alkyl-amino, C
1
-C
8
-alkylthio, C
2
-C
5
-alkenylthio, C
2
-C
5
-alkinylthio or C
3
-C
7
-cycloalkylthio, represent in each case optionally halogen-, nitro-, cyano-, C
1
-C
4
-alkoxy-, C
1
-C
4
-halogenoalkoxy-, C
1
-C
4
-alkylthio-, C
1
-C
4
-halogenoalkylthio-, C
1
-C
4
-alkyl- or C
1
-C
4
-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent in each case optionally halogen-substituted C
1
-C
10
-alkyl, C
1
-C
10
-alkoxy, C
3
-C
8
-alkenyl or C
1
-C
8
-alkoxy-C
1
-C
8
-alkyl, represent optionally halogen-, C
1
-C
6
-halogenoalkyl-, C
1
-C
6
-alkyl- or C
1
-C
6
-alkoxy-substituted phenyl, represent optionally halogen-, C
1
-C
6
-alkyl-, C
1
-C
6
-halogenoalkyl- or C
1
-C
6
-alkoxy-substituted benzyl or together represent a 5- or 6-membered ring which is optionally interrupted by oxygen or sulphur and which may optionally be substituted by C
1
-C
6
-alkyl,
and bioactive compounds, preferably
(1) the phenylhydrazine derivative of the formula
known from WO 93/10 083
and/or
(2) the macrolide with the common name abamectin (III)
known from DE-A-27 17 040
and/or
(3) the naphthalenedione derivative of the formula
known from DE-A-26 41 343
and/or
(4) the pyrrole derivative of the formula
known from EP-A-347 488
and/or
(5) the thiourea derivative of the formula
known from EP-A-210 487
and/or
(6) the oxazoline derivative of the formula
known from WO 93/22 297
and/or
(7) an organotin derivative of the formula
(VIIIa=azocyclotin),
known from The Pesticide Manual, 9th edition, p.48
or
R represents —OH
(VIIIb=cyhexatin),
known from U.S. Pat. No. 3,264,177
and/or
(8) the pyrazole derivative of the formula
known from EP-A-289 879
and/or
(9) the pyrazole derivative of the formula
known from EP-A-234 045
and/or
(10) the pyridazinone derivative of the formula
known from EP-A-134 439
and/or
(11) the benzoylurea of the formula
known from EP-A-161 019
and/or
(12) the pyrethroid of the formula
known from EP-A-049 977
and/or
(13) the tetrazine derivative of the formula
known from EP-A-005 912
and/or
(14) the organotin derivative of the formula
known from DE-A-2 115 666
and/or
(15) the sulphenamide of the formula
known from The Pesticide Manual, 11th edition, 1997, page 1208
and/or
(16) the pyrimidyl phenol ethers
R=Cl (XVII); (4-[(4-chloro-&agr;,&agr;,&agr;-trifluoro-3-tolyl)oxy]-6-[(&agr;,&agr;,&agr;-4-tetrafluoro-3-tolyl)oxy]-pyrimidine)
R=NO
2
(XVIII); 4-[(4-chloro-&agr;,&agr;,&agr;-trifluoro-3-tolyl)oxy]-6-[(&agr;,&agr;,&agr;-trifluoro-4-nitro-3-tolyl)oxy]-pyrimidine
R=Br (XIX); 4-[(4-chloro-&agr;,&agr;,&agr;-trifluoro-3-tolyl)oxy]-6-[(&agr;,&agr;,&agr;-tri-fluoro-4-bromo-3-tolyl)oxy]-pyrimidine
known from WO 94/02 470, EP-A-883 991
and/or
(17) the macrolide of the formula
(spinosad) a mixture preferably comprising
85% spinosyn A R=H
15% spinosyn B R=CH
3
known from EP-A-375 316
and/or
(18) ivermectin (XXI)
known from EP-A-001 689
and/or
(19) milbemectin (XXII)
known from The Pesticide Manual, 11th edition, 1997, p. 846
and/or
(20) endosulfan (XXIII)
known from DE-A-1 015 797
and/or
(21) fenazaquin (XXIV)
known from EP-A-326 329
and/or
(22) pyrimidifen (XXV)
known from EP-A-196 524
and/or
(23) triarathen (XXVI)
known from DE-A-2 724 494
and/or
(24) tetradifon (XXVII)
known from U.S. Pat. No. 2,812,281
and/or
(25) propargit (XXVIII)
known from U.S. Pat. No. 3,272,854
and/or
(26) hexythiazox (XXIX)
known from DE-A-3 037 105
and/or
(27) bromopropylate (XXX)
known from U.S. Pat. No. 3,784,696
and/or
(28) dicofol (XXXI)
known from U.S. Pat. No. 2,812,280
and/or
(29) chinomethionat (XXXII)
known from DE-A-1 100 372
have very good insecticidal and acaricidal properties.
Surprisingly, the insecticidal and acaricidal action of the active compound combinations according to the invention considerably exceeds the total of the actions of the individual active compounds. A
Bretschneider Thomas
Erdelen Christoph
Fischer Reiner
Bayer Aktiengesellschaft
Henderson Richard E. L.
Pryor Alton N.
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