Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – N-c doai
Reexamination Certificate
1999-10-29
2001-12-11
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
N-c doai
C514S456000, C514S466000, C514S476000, C514S528000, C514S539000
Reexamination Certificate
active
06329424
ABSTRACT:
The present invention relates to novel crop-protecting mixtures of active ingredients having a synergistically increased microbicidal action and comprising at least two active components, and to methods of using such mixtures in crop protection, in particular for controlling and preventing the incidence of diseases.
Component I is a compound of the formula I
in which:
X is CH or N;
R is CH
3
or cyclopropyl;
Y is H, F, Cl, Br, CF
3
, CF
3
O, propargyloxy;
Z is H, F, Cl, CF
3
, CF
3
O; or
Y and Z together are a methylenedioxy, a (difluoromethylene)dioxy, an ethylenedioxy, a (trifluoroethylene)dioxy or a benzo group.
These compounds have been described in EP-A-403 618, EP-A-460 575, WO 92/18494 and other publications.
Component II is a compound selected from the group consisting of
II A) methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (“metalaxyl”; GB-1 500 581), in particular its R enantiomer,
II B) methyl N-(2-methoxyacetyl)-N-(2,6xylyl)-D-alaninate (“R-metalaxyl”; GB-1 500 581),
II C) methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate (“furalaxyl”; GB-1 448 810),
II D) methyl N-phenylacetyl-N-2,6xylyl-DL-alaninate (“benalaxyl”; DE-29 03 612),
II E) (±)-&agr;-(2-chloro-N-2,6-xylylacetamido)-&ggr;-butyrolactone (“ofurace”; U.S. Pat. No. 4,141,989),
II F) 2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)-acet-2′,6′-xylidide (“oxadixyl”; GB-P. 2 058 059),
II G) 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea, (“cymoxanil”; U.S. Pat. No. 3,957,847) and
II H) manganese ethylenebis(dithiocarbamate) polymer zinc complex (“mancozeb”; U.S. Pat. No. 2,974,156).
The invention furthermore relates to mixtures in which in component I of the formula I:
X is CH or N;
R is CH
3
or cyclopropyl;
Y is H, F, Cl, Br, CF
3
, CF
3
O, propargyloxy;
Z is H, F, Cl; or
Y and Z together are a methylenedioxy, a (difluoromethylene)dioxy, an ethylenedioxy, a (trifiuoroethylene)dioxy or a benzo group; and in which component II is a compound selected from the group consisting of
II A) methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (“metalaxyl”), in particular its R enantiomer,
II B) methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-D-alaninate (“R-metalaxyl”),
II C) methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate (“furalaxyl”),
II D) methyl N-phenylacetyl-N-2,6-xylyl-DL-alaninate (“benalaxyl”),
II E) (±)-&agr;-(2-chloro-N-2,6-xylylacetamido)-&ggr;-butyrolactone (“ofurace”),
II F) 2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)-acet-2′,6′-xylidide (“oxadixyl”), and
II G) 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea (“cymoxanil”).
Surprisingly, it has emerged that in the prevention and control of plant diseases the mixtures according to the invention, of components I and II, not only exert a mutually complementary action against a variety of target pathogens or a purely additive action against the same pathogens, but that they display a pronounced, synergistically increased action.
Advantageous mixing ratios of the two active ingredients are I:II=25:1 to 1:20, preferably I:II=20:1 to 1:10 and 12:1 to 1:8.
Particularly advantageous mixing ratios are
I:IIA=10:1 to 1:10
I:IIB=10:1 to 1:8
I:IIC=6:1 to 1:8
I:IID=8:1 to 1:4
I:IIE=10:1 to 1:6
I:IIF=10:1 to 1:8
I:IIG=10:1 to 1:5
I:IIH=1:30 to 1:1
Preferred two-component mixtures are those in which component I is selected from the group consisting of the following compounds:
(01) methyl 3-methoxy-2-[&agr;-{[(&agr;-cyclopropyl-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]acrylate;
(02) methyl 3-methoxy-2-[&agr;-{[(&agr;-cyclopropyl-3,4-(difluoromethylenedioxy)benzyl)imino]oxy}-o-tolyl]acrylate;
(03) methyl 2-[&agr;-{[(&agr;-methyl-3-bromobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(04) methyl 2-[&agr;-{[(&agr;-cyclopropyl-3,4-methylenedioxybenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(05) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3-propargyloxybenzyl)imino]oxy}-o-tolyl]acrylate;
(06) methyl 2-[&agr;-{[(&agr;-methyl-3,4-(difluoromethylenedioxy)benzyl)imino]-oxy}-o-tolyl]glyoxylate O-methyloxime;
(07) methyl 3-methoxy-2-[&agr;-{[(&agr;-cyclopropyl-3,4-methylenedioxybenzyl)imino]oxy}-o-tolyl]acrylate;
(08) methyl 2-[&agr;-{[(&agr;-methyl-3-propargyloxybenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(09) methyl 2-[&agr;-{[(&agr;-cyclopropyl-4-fluorobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(10) methyl 2-[&agr;-{[(&agr;-methyl-4-fluoro-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(11) methyl 3-methoxy-2-[&agr;-{[(1-(&bgr;-naphthyl)ethyl)imino]oxy}-o-tolyl]acrylate;
(12) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3,4-methylenedioxybenzyl)imino]oxy}-o-tolyl]acrylate;
(13) methyl 2-[&agr;-{[(&agr;-methyl-3-chlorobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(14) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3,4-ethylenedioxybenzyl)imino]oxy}-o-tolyl]acrylate;
(15) methyl 2-[&agr;-{[(&agr;-cyclopropyl-4-chlorobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(16) methyl 3-methoxy-2-[&agr;-{[(&agr;-cyclopropyl-3-chlorobenzyl)imino]oxy}-o-tolyl]acrylate;
(17) methyl 2-[&agr;{[(&agr;-cyclorpropyl-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(18) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3-trifluoromethoxybenzyl)imino]oxy}-o-tolyl]acrylate;
(19) methyl 2-[&agr;-{[(&agr;-methyl-3,4-methylenedioxybenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(20) methyl 2-[&agr;-{[(&agr;-cyclopropyl-3,4-(difluoromethylenedioxy)benzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(21) methyl 2-[&agr;-{[(&agr;-methyl-3,4-ethylenedioxybenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(22) methyl 3-methoxy-2-[&agr;-{[(1-(2,3-dihydro-2,2,3-trifluoro-1,4-benzodioxan-6-yl)ethyl)imino]oxy}-o-tolyl]acrylate;
(23) 2-[&agr;-{[(1-(2,3-dihydro-2,2,3-trifluoro-1,4-benzodioxan-6-yl)ethyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(24) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]acrylate;
(25) methyl 2-[&agr;-{[(&agr;-methyl-4-chlorobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(26) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-4-chlorobenzyl)imino]oxy}-o-tolyl]acrylate;
(27) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3-bromobenzyl)imino]oxy}-o-tolyl]acrylate;
(28) methyl 2-[&agr;-{[(1-(&bgr;-naphthyl)ethyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(29) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3,4-(difluoromethylenedioxy)benzyl)imino]oxy}-o-tolyl]acrylate;
(30) methyl 3-methoxy-2-[&agr;-{[(&agr;-cyclopropyl-4-fluorobenzyl)imino]oxy}-o-tolyl]acrylate;
(31) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-4-fluoro-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]acrylate;
(32) methyl 2-[&agr;-{[(&agr;-methyl-3-trifluoromethoxybenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(33) methyl 2-[&agr;-{[(&agr;-cyclopropyl-3-chlorobenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(34) methyl 3-methoxy-2-[&agr;-{[(&agr;-methyl-3-chlorobenzyl)imino]oxy}-o-tolyl]acrylate;
(35) methyl 2-[&agr;-{[(&agr;-methyl-3-trifluoromethylbenzyl)imino]oxy}-o-tolyl]glyoxylate O-methyloxime;
(36) methyl 3-me
Knauf-Beiter Gertrude
Zeun Ronald
Bayer Aktiengesellschaft
Gil Joseph C.
Robinson Allen J.
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