U.S. patent application number 12/441407 was filed with the patent office on 2010-02-18 for ternary pesticidal mixtures.
Invention is credited to Jurgen Langewald, Reinhard Stierl.
Application Number | 20100041682 12/441407 |
Document ID | / |
Family ID | 38956386 |
Filed Date | 2010-02-18 |
United States Patent
Application |
20100041682 |
Kind Code |
A1 |
Langewald; Jurgen ; et
al. |
February 18, 2010 |
Ternary Pesticidal Mixtures
Abstract
Ternary pesticidal mixtures comprising, as active components, an
anthranilamid compound of the formula (I) wherein the variables are
defined according to the description, and two fungicidal compounds
II and III selected from the following groups: azoles,
strobilurins, carboxamides, heterocylic compounds, carbamates,
guanidines, antibiotics, nitrophenyl derivates, sulfur-containing
heterocyclyl compounds, organometal compounds and other active
compounds according to the description, in a synergistically
effective amount, methods for controlling pests, and harmful fungi,
methods of protecting plants from attack or infestation by insects,
acarids or nematodes, methods for treating, controlling, preventing
or protecting an animal against infestation or infection by
parasites, compositions containing these mixtures, and methods for
their preparation. ##STR00001##
Inventors: |
Langewald; Jurgen;
(Mannheim, DE) ; Stierl; Reinhard; (Kaohsiung
County, TW) |
Correspondence
Address: |
BRINKS, HOFER, GILSON & LIONE
P.O. BOX 1340
MORRISVILLE
NC
27560
US
|
Family ID: |
38956386 |
Appl. No.: |
12/441407 |
Filed: |
September 17, 2007 |
PCT Filed: |
September 17, 2007 |
PCT NO: |
PCT/EP2007/059762 |
371 Date: |
March 16, 2009 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
60845382 |
Sep 18, 2006 |
|
|
|
60885273 |
Jan 17, 2007 |
|
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Current U.S.
Class: |
514/269 ;
514/399; 514/406 |
Current CPC
Class: |
A61K 31/429 20130101;
A61K 31/277 20130101; A01N 43/78 20130101; A01N 37/34 20130101;
A61K 31/165 20130101; A61P 33/14 20180101; A61K 31/428 20130101;
A61K 31/4155 20130101; A01N 37/42 20130101; A61K 31/433 20130101;
Y02A 50/409 20180101; Y02A 50/411 20180101; Y02A 50/30 20180101;
A61K 31/426 20130101; Y02A 50/387 20180101; A01N 43/82 20130101;
A61K 31/4439 20130101; A01N 43/80 20130101; Y02A 50/385 20180101;
A61P 33/00 20180101; A01N 53/00 20130101; A61K 31/437 20130101;
A01N 43/56 20130101; A01N 43/90 20130101; A01N 43/56 20130101; A01N
37/50 20130101; A01N 43/56 20130101; A01N 43/90 20130101; A01N
47/24 20130101; A01N 47/38 20130101; A01N 43/56 20130101; A01N
2300/00 20130101 |
Class at
Publication: |
514/269 ;
514/406; 514/399 |
International
Class: |
A01N 43/56 20060101
A01N043/56; A01N 43/50 20060101 A01N043/50; A01N 43/54 20060101
A01N043/54; A01P 3/00 20060101 A01P003/00; A01P 7/04 20060101
A01P007/04; A01P 5/00 20060101 A01P005/00 |
Claims
1-28. (canceled)
29. A ternary pesticidal mixture comprising, as active components:
1) an anthranilamide sulfamoyl compound of the formula I
##STR00004## in which the substituents are as defined below:
B.sup.1 is hydrogen, cyano or chlorine; B.sup.2 is bromine or
CF.sub.3; and R is hydrogen or C.sub.1-C.sub.6-alkyl; 2) a
fungicidal compound II selected from the group consisting of: A) an
azole, selected from the group consisting of bitertanol,
bromuconazole, cyproconazole, difenoconazole, diniconazole,
enilconazole, epoxiconazole, fluquinconazole, fenbuconazole,
flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,
metconazole, myclobutanil, penconazole, propiconazole,
prothioconazole, simeconazole, triadimefon, triadimenol,
tebuconazole, tetraconazole, and triticonazole; prochloraz,
pefurazoate, imazalil, triflumizole, cyazofamid, benomyl,
carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole,
or hymexazole; B) a strobilurin, selected from the group consisting
of azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin,
kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,
pyraclostrobin, and trifloxystrobin; C) a carboxamide, selected
from the group consisting of carboxin, benalaxyl, boscalid,
fenhexamid, flutolanil, mepronil, metalaxyl, mefenoxam, ofurace,
oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, dimethomorph,
and flumorph; fluopicolide (picobenzamid), zoxamide, diclocymet, or
mandipropamid; D) a heterocylic compound, selected from the group
consisting of fluazinam, and pyrifenox; bupirimate, cyprodinil,
fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil,
triforine, triazoxide, fenpiclonil, fludioxonil, dodemorph,
fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone,
vinclozolin, famoxadone, fenamidone, probenazole, amisulbrom,
anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole,
acibenzolar-5-methyl, captafol, captan, folpet, fenoxanil, or
quinoxyfen; E) a carbamate, selected from the group consisting of
mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb,
and ziram; diethofencarb, iprovalicarb, flubenthiavalicarb, or
propamocarb; and F) other active compounds, selected from the group
consisting of guanidines comprising dodine, iminoctadine, or
guazatine; antibiotics comprising kasugamycin, polyoxine, or
validamycin A; nitrophenyl derivates comprising dinocap;
sulfur-containing heterocyclyl compounds comprising dithianon or
isoprothiolane; organometal compounds comprising fentin salts;
organophosphorus compounds comprising edifenphos, iprobenfos,
fosetyl-aluminum, pyrazophos, or tolclofos-methyl; organochlorine
compounds comprising chlorothalonil, dichlofluanid, flusulfamide,
hexachlorobenzene, phthalide, pencycuron, quintozene or
tolylfluanid; inorganic active compounds comprising Bordeaux
mixture, copper hydroxide, copper oxychloride, basic copper
sulfate, or sulfur; and others comprising cyflufenamid, cymoxanil,
dimethirimol, ethirimol, furalaxyl, metrafenone or spiroxamine; and
3) a fungicidal compound III selected from the group consisting of
groups A) to F) above, and G) to J): G) strobilurins selected from
the group consisting of methyl
(2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate,
methyl
(2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate
and methyl
2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate;
H) carboxamides selected from the group consisting of furametpyr,
tiadinil,
N-(4'-bromo-biphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamid-
e,
N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-
-carboxamide,
N-(4'-chloro-3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide,
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide,
3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carbox-amide,
N-(2',4'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(2',4'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(2',4'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-11H-pyrazole-4--
carboxamide,
N-(2',4'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoro-methyl-1H-pyrazole-4-
-carboxamide,
N-(2',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(2',5'-difluoro-biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4--
carboxamide,
N-(2',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(3',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoro-methyl-1H-pyrazole-4-
-carboxamide,
N-(3',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(3',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(3',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(3'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide,
N-(3'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide,
N-(3'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide,
N-(3'-chlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4--
carboxamide,
N-(2'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide,
N-(2'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide,
N-(2'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide,
N-(2'-chlorbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl)-1-methyl-3-trifluoromethy-
l-1H-pyrazole-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoro-methyl-1H-pyrazo-
le-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide,
N-(2',4',5'-trifluoro-biphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazol-
e-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide,
N-[2-(1,1,2,3,3,3-hexa-fluoro-propoxy)-phenyl]-1-methyl-3-trifluoromethyl-
-1H-pyrazole-4-carboxamide,
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide,
N-[2-(2-chloro-1,1,2-trifluoro-ethoxy)-phenyl]-1-methyl-3-trifluoromethyl-
-1H-pyrazole-4-carboxamide,
N-[2-(2-chlor-1,1,2-trifluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H--
pyrazole-4-carboxamide,
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide,
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-pyr-
azole-4-carboxamide,
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoro-methyl-1-methyl-1H-p-
yrazole-4-carboxamide, and
N-(4'-(trifluoromethyl-thio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H--
pyrazole-4-carboxamide;
5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
[2-(1,2-dimethylpropyl)-phenyl]-amide, flumetover, carpropamid,
N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-metha-
nesulfonylamino-3-methylbutyramide, or
N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-etha-
nesulfonylamino-3-methyl-butyramide; I) heterocylic compounds,
selected from the group consisting of aldimorph, octhilinone,
amisulbrom, diclomezine,
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine,
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne,
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine,
5-methyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-
-ylamine,
5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine, 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine
and
5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimid-
ine-7-ylamine, and 2-butoxy-6-iodo-3-propylchromen-4-one; dazomet,
or 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine;
and J) other active compounds, selected from the group consisting
of metam,
methyl-3-(4-chlorophenyl)-3-(2-isopropoxycarbonylainino-3-methylbutyrylam-
ino)propaonate, streptomycin, binapacryl, dinobuton,
fentin-acetate, fosetyl, phosphorous acid and its salts,
hexachlorobenzene, thiophanate-methyl, and copper acetate; in a
synergistically effective amount.
30. The pesticidal mixture of claim 29, comprising the compound of
formula I and the compound II in a weight ratio of from 100:1 to
1:100.
31. The pesticidal mixture of claim 29, wherein the compound of
formula I is
3-bromo-4'-cyano-1-(3-chloro-2-pyridyl)-2'-methyl-6'-(methylcarbamoyl)-
pyrazole-5-carboxanilide.
32. The pesticidal mixture of claim 29, wherein the compound of
formula I is
3-bromo-4'-chloro-1-(3-chloro-2-pyridyl)-2'-methyl-6'-(methylcarbamoyl-
)pyrazole-5-carboxanilide.
33. The pesticidal mixture of claim 29, wherein compound II is a
strobilurin.
34. The pesticidal mixture of claim 29, wherein compound II is
selected from the group consisting of azoxystrobin, dimoxystrobin,
enestroburin, metominostrobin, and orysastrobin.
35. The pesticidal mixture of claim 29, wherein compound II is
orysastrobin.
36. The pesticidal mixture of claim 29, wherein compound II is
triflumizole.
37. The pesticidal mixture of claim 29, wherein compound II is
selected from the group consisting of carpropamid, diclocymet,
furametpyr, thifluzamide, and tiadinil.
38. The pesticidal mixture of claim 29, wherein compound II is
selected from the group consisting of probenazole, pyroquilon, and
tricyclazole.
39. A pesticidal mixture of claim 29, wherein compound III is
selected from the group consisting of groups A) to F).
40. The pesticidal mixture of claim 29, wherein compound III is
selected from the group consisting of groups G) to J).
41. The pesticidal mixture of claim 29, wherein compound III is
selected from group H).
42. The pesticidal mixture of claim 29, wherein compound III is
N-(4'-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide-
,
N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(4'-chloro-3'-fluoro-biphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-
-carboxamide,
N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide,
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide,
3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide,
N-(2',4'-difluoro-biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-
-carboxamide,
N-(2',4'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(2',4'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arbox-amide,
N-(2',4'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(2',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoro-methyl-1H-pyrazole-4-
-carboxamide,
N-(2',5'-difluorobiphenyl-2-yl)-3-difluoro-methyl-1-methyl-1H-pyrazole-4--
carboxamide,
N-(2',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(3',5'-difluoro-biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-
-carboxamide,
N-(3',5'-dichloro-biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-
-carboxamide,
N-(3',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arbox-amide,
N-(3',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arbox-amide,
N-(3'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide,
N-(3'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide,
N-(3'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide,
N-(3'-chlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4--
carboxamide,
N-(2'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide,
N-(2'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide,
N-(2'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide,
N-(2'-chlorbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide,
N-(2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl)-1-methyl-3-trifluoromethyl-
-1H-pyrazole-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazol-
e-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide,
N-(2',4',5'-trifluoro-biphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazol-
e-4-carboxamide,
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide,
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-
-pyrazole-4-carboxamide,
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoro-methyl-1-methyl-1-
H-pyrazole-4-carboxamide,
N-[2-(2-chloro-1,1,2-trifluoro-ethoxy)phenyl]-1-methyl-3-trifluoromethyl--
1H-pyrazole-4-carboxamide,
N-[2-(2-chlor-1,1,2-trifluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H--
pyrazole-4-carboxamide,
4-carbonsaure-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-difluoromethyl-1--
methyl-1H-pyrazole-4-carboxamide,
N-[2-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-py-
razole-4-carboxamide,
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-py-
razole-4-carboxamide, or
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-p-
yrazole-4-carboxamide.
43. The pesticidal mixture of claim 29, wherein compound III is
selected from the group consisting of
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine,
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne,
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine,
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine--
7-ylamine,
5-methyl-6-octyl-[1,2,4]triazolo-[1,5-a]pyrimidine-7-ylamine,
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine, 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
and
5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimid-
ine-7-yl-amine.
44. The pesticidal mixture of claim 29, wherein compound III is
selected from the group consisting of
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne,
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine,
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine--
7-ylamine,
5-methyl-6-octyl-[1,2,4]triazolo-[1,5-a]pyrimidine-7-yl-amine,
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine, 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
and
5-trifluoromethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidi-
ne-7-yl-amine.
45. A pesticidal composition, comprising a liquid or solid carrier
and the mixture of claim 29.
46. A method for controlling phytopathogenic harmful fungi, wherein
the fungi, their habitat or the plants to be protected against
fungal attack, the soil or seed are treated with an effective
amount of the mixture of claim 29.
47. A method for controlling insects, arachnids or nematodes
comprising contacting an insect, acarid or nematode or their food
supply, habitat, breeding grounds or their locus with the mixture
of claim 29 in pesticidally effective amounts.
48. A method for protecting plants from attack or infestation by
insects, acarids or nematodes comprising contacting the plant, or
the soil or water in which the plant is growing, with the mixture
of claim 29 in pesticidally effective amounts.
49. The method of claim 47, wherein the mixture is applied in an
amount of from 5 g/ha to 2000 g/ha.
50. A method for protection of seed comprising contacting the seed
with the mixture of claim 29 in pesticidally effective amounts.
51. The method of claim 50 wherein the mixture is applied in an
amount of from 0.001 g to 10 kg per 100 kg of seeds.
52. Seed, comprising the mixture of claim 29 in an amount of from
0.1 g to 10 kg per 100 kg of seeds.
53. The method of claim 46 wherein the compound of formula I and
the compound II are applied simultaneously, separately, or in
succession.
54. A method for treating, controlling, preventing or protecting a
warm-blooded animal or a fish against infestation or infection by
parasites which comprises orally, topically or parenterally
administering or applying to said animal or fish a parasiticidally
effective amount of the mixture of claim 29.
Description
[0001] The present invention relates to ternary pesticidal mixtures
comprising, as active components, [0002] 1) an anthranilamide
compound of formula I
[0002] ##STR00002## [0003] in which the substituents are as defined
below: [0004] B.sup.1 is hydrogen, cyano or chlorine; [0005]
B.sup.2 is bromine or CF.sub.3; and [0006] R is hydrogen or
C.sub.1-C.sub.6-alkyl; and [0007] 2) one fungicidal compound II
selected from the following groups: [0008] A) azoles, in
particular: bitertanol, bromuconazole, cyproconazole,
difenoconazole, diniconazole, enilconazole (imazalil),
epoxiconazole, fluquinconazole, fenbuconazole, flusilazole,
flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole,
myclobutanil, penconazole, propiconazole, prothioconazole,
simeconazole, triadimefon, triadimenol, tebuconazole,
tetraconazole, triticonazole; [0009] prochloraz, pefurazoate,
imazalil, triflumizole, cyazofamid; [0010] benomyl, carbendazim,
thiabendazole, fuberidazole; [0011] ethaboxam, etridiazole,
hymexazole; [0012] B) strobilurins, in particular: azoxystrobin,
dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,
metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,
trifloxystrobin; [0013] C) carboxamides, in particular: carboxin,
benalaxyl, boscalid, fenhexamid, flutolanil, mepronil, metalaxyl,
mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad,
thifluzamide, 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
[2-(1,2-dimethyl-propyl)-phenyl]-amide, dimethomorph, flumorph;
[0014] fluopicolide (picobenzamid), zoxamide; [0015] diclocymet,
mandipropamid; [0016] D) heterocylic compounds, in particular:
fluazinam, pyrifenox; [0017] bupirimate, cyprodinil, fenarimol,
ferimzone, mepanipyrim, nuarimol, pyrimethanil; [0018] triforine,
triazoxide; [0019] fenpiclonil, fludioxonil; [0020] dodemorph,
fenpropimorph, tridemorph; fenpropidin, prodione, procymidone,
vinclozolin; [0021] famoixadone, fenamidone, probenazole; [0022]
amisulbrom, anilazine, diclomezine, pyroquilon, proquinazid,
tricyclazole; acibenzolar-S-methyl, captafol, captan, folpet,
fenoxanil, quinoxyfen; [0023] E) carbamates, in particular:
mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb,
ziram; [0024] diethofencarb, iprovalicarb, flubenthiavalicarb,
propamocarb; [0025] methyl
3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)prop-
anoate; and [0026] F) other active compounds, selected from [0027]
guanidines: dodine, iminoctadine, guazatine; [0028] antibiotics:
kasugamycin, polyoxine, validamycin A; [0029] nitrophenyl
derivates: dinocap, [0030] sulfur-containing heterocyclyl
compounds: dithianon, isoprothiolane; [0031] organometal compounds:
fentin salts [0032] organophosphorus compounds: edifenphos,
iprobenfos, fosetyl-aluminum, pyrazophos, tolclofos-methyl; [0033]
organochlorine compounds: chlorothalonil, dichlofluanid,
flusulfamide, phthalide, pencycuron, quintozene, tolylfluanid;
[0034] inorganic active compounds: Bordeaux mixture, copper
hydroxide, copper oxychloride, basic copper sulfate, sulfur; [0035]
others: cyflufenamid, cymoxanil, dimethirimol, ethirimol,
furalaxyl, metrafenone and spiroxamine; and [0036] 3) one
fungicidal compound III selected from the groups A) to F) above and
G) to J): [0037] G) strobilurins selected from: methyl
(2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate,
methyl
(2-chloro-5-[1-(6-methylpyridin-2-yl-methoxyimino)ethyl]benzyl)carbamate
and methyl
2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate;
[0038] H) carboxamides selected from: furametpyr, tiadinil,
N-(4'-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide-
,
N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(4'-chloro-3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide,
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide;
3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide;
N-(2',4'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',4'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',4'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',4'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(3',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide, [0039]
N-(3',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide, [0040]
N-(3'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide;
N-(3'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-
-carboxamide, [0041]
N-(3'-chlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide;
N-(2'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-
-carboxamide;
N-(2'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide;
N-(2'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-
-carboxamide;
N-(2'-chlorbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxa-
mide;
N-(2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl)-1-methyl-3-trifluorom-
ethyl-1H-pyrazole-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazol-
e-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide;
N-(2',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide;
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-
-pyrazole-4-carboxamide;
N-[2-(1,1,2,3,3,3-hexafluor-opropoxy)-phenyl]-3-difluoromethyl-1-methyl-1-
H-pyrazole-4-carboxamide, [0042]
N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1-
H-pyrazole-4-carboxamide;
N-[2-(2-chlor-1,1,2-trifluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H--
pyrazole-4-carboxamide;
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide;
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-methyl-3-trifluoro-methyl-1H-py-
razole-4-carboxamide;
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-py-
razole-4-carboxamide;
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-p-
yrazole-4-carboxamide;
5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
[2-(1,2-dimethyl-propyl)-phenyl]-amide, [0043] flumetover,
carpropamid, and [0044]
N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-metha-
nesulfonylamino-3-methylbutyramide,
N-(2-{4-[3-(4-chlorophenyl)-prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-etha-
nesulfonylamino-3-methylbutyramide; [0045] I) heterocylic
compounds, selected from: [0046] aldimorph, octhilinone,
amisulbrom, diclomezine, [0047]
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2-
,4]triazolo[1,5-a]pyrimidine,
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne,
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine,
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine--
7-ylamine,
5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine, 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine
and
5-trifluoromethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidi-
ne-7-ylamine, [0048] 2-butoxy-6-iodo-3-propylchromen-4-one; [0049]
dazomet,
3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; and
[0050] J) other active compounds, selected from metam,
methyl-3-(4-chloro-phenyl)-3-(2-isopropoxycarbonylamino-3-methyl-butyryla-
mino)propaonate; streptomycin, binapacryl, dinobuton; [0051]
fentin-acetate, fosetyl, phosphorous acid and its salts,
hexachlorobenzene, thiophanate-methyl, and [0052] copper acetate;
in a synergistically effective amount.
[0053] Moreover, the invention relates to a method for controlling
pests, this includes animal pests and harmful fungi, using mixtures
of a compound I with active compounds II and III, and to the use of
the compounds I with the active compounds II and III for preparing
such mixtures, and also to compositions comprising such
mixtures.
[0054] In one embodiment the present invention provides methods for
the control of insects, acarids or nematodes comprising contacting
the insect, acarid or nematode or their food supply, habitat,
breeding grounds or their locus with a pesticidally effective
amount of mixtures of a compound I with two compounds II and
III.
[0055] Moreover, in another embodiment the present invention also
relates to a method of protecting plants from attack or infestation
by insects, acarids or nematodes comprising contacting the plant,
or the soil or water in which the plant is growing, with a
pesticidally effective amount of a mixture of a compound I with two
compounds II and III.
[0056] This invention also provides a method for treating,
controlling, preventing or protecting an animal against infestation
or infection by parasites which comprises orally, topically or
parenterally administering or applying to the animals a
parasiticidally effective amount of a mixture of a compound I with
two compounds II and III.
[0057] The invention also provides a process for the preparation of
a composition for treating, controlling, preventing or protecting a
warm-blooded animal or a fish against infestation or infection by
insects, acarids or nematodes which comprises a pesticidally
effective amount of a mixture of a compound I with two compounds II
and III.
[0058] Moreover, the invention relates to a method for controlling
harmful fungi using mixtures of a compound I with active compounds
II and III and to the use of a compound I with active compounds II
and III for preparing such mixtures, and also to compositions
comprising these mixtures.
[0059] The anthranilamide compound of formula I referred to above
as component 1, their preparation and their action against insect
and acarid pests are known (WO 2004/67528; WO 2004/46129; WO
2004/33468; WO 2003/24222; WO 2003/15518). Mixtures, active against
pests, of compounds of formula I with other insecticides are known
in a general manner from WO 2004/67528; WO 2004/46129; WO
2004/33468; WO 2003/24222; WO 2003/15518. WO 2006/055922 discloses
anthranilamide derivatives as single compounds, and in mixtures.
Binary mixtures of compounds of formula I with fungicides are
described in WO 2006/108552.
[0060] The active compounds II and III mentioned above as component
2 and 3, their preparation and their action against harmful fungi
are generally known (cf.:
http://www.hclrss.demon.co.uk/index.html); they are commercially
available. Particularly, they are known from: bitertanol,
.beta.-([1,1'-biphenyl]-4-yloxy)-.alpha.-(1,1-dimethylethyl)-1H-1,2,4-tri-
azole-1-ethanol (DE 23 24 020), bromuconazole,
1-[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1H-1,2,4-t-
riazole (Proc. 1990 Br. Crop. Prot. Conf.--Pests Dis. Vol. 1, p.
459); cyproconazole,
2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-ylbutan-2-ol
(U.S. Pat. No. 4,664,696); difenoconazole,
1-{2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-[1,3]dioxolan-2-ylmeth-
yl}-1H-[1,2,4]triazole (GB-A 2 098 607); diniconazole,
(.beta.E)-.beta.-[(2,4-dichlorophenyl)methylene]-.alpha.-(1,1-dimethyleth-
yl)-1H-1,2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol. 8, p.
575); enilconazole (imazalil),
1-[2-(2,4-dichlorphenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole
(Fruits, 1973, Vol. 28, p. 545); epoxiconazole, (2
RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,-
4-triazole (EP-A 196 038); fluquinconazole,
3-(2,4-dichlorophenyl)-6-fluoro-2-[1,2,4]-triazol-1-yl-3H-quinazolin-4-on-
e (Proc. Br. Crop Prot. Conf.--Pests Dis., 5-3, 411 (1992));
fenbuconazole,
.alpha.-[2-(4-chlorophenyl)ethyl]-.alpha.-phenyl-1H-1,2,4-triazole-1-prop-
anenitrile (Proc. 1988 Br. Crop Prot. Conf.--Pests Dis. Vol. 1, p.
33); flusilazole,
1-{[bis-(4-fluorophenyl)methylsilanyl]methyl}-1H-[1,2,4]triazole
(Proc. Br. Crop Prot. Conf.--Pests Dis., 1, 413 (1984));
flutriafol,
.alpha.-(2-fluorophenyl)-.alpha.-(4-fluorophenyl)-1H-1,2,4-triazole-1-eth-
anol (EP 15 756); hexaconazole,
2-(2,4-dichlorophenyl)-1-[1,2,4]triazol-1-ylhexan-2-ol (CAS RN
79983-71-4); imibenconazole, (4-chlorophenyl)methyl
N-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanimidothioate
((Proc. 1988 Br. Crop Prot. Conf.--Pests Dis. Vol. 2, p. 519);
imidothioate ((Proc. 1988 Br. Crop Prot. Conf.--Pests Dis. Vol. 2,
p. 519); ipconazole,
2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmeth-
yl)cyclopentanol (EP 267 778); metconazole,
5-(4-chlorobenzyl)-2,2-dimethyl-1-[1,2,4]triazol-1-ylmethylcyclopentanol
(GB 857 383); myclobutanil,
2-(4-chlorophenyl)-2-[1,2,4]triazol-1-ylmethylpentanenitrile (CAS
RN 88671-89-0); penconazole,
1-[2-(2,4-dichlorophenyl)pentyl]-1H-[1,2,4]triazole (Pesticide
Manual, 12th Ed. (2000), p. 712); propiconazole,
1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-tr-
iazole (BE 835 579); prothioconazole,
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydr-
o-[1,2,4]triazole-3-thione (WO 96/16048); simeconazole,
.alpha.-(4-fluorophenyl)-.alpha.-[(trimethylsilyl)methyl]-1H-1,2,4-triazo-
le-1-ethanol [CAS RN 149508-90-7]; triadimefon,
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone;
triadimenol,
P3-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-etha-
nol; tebuconazole,
1-(4-chlorophenyl)-4,4-dimethyl-3-[1,2,4]triazol-1-ylmethylpentan-3-ol
(EP-A 40 345); tetraconazole,
1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-t-
riazole (EP 234 242); triticonazole,
(5E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylm-
ethyl)cyclopentanol (FR 26 41 277); prochloraz,
N-{propyl-[2-(2,4,6-trichlorophenoxy)ethyl]}imidazole-1-carboxamide
(U.S. Pat. No. 3,991,071); pefurazoate, 4-pentenyl
2-[(2-furanylmethyl)(1H-imidazol-1-ylcarbonyl)amino]butanoate [CAS
RN 101903-30-4]; triflumizole,
(4-chloro-2-trifluoromethylphenyl)-(2-propoxy-1-[1,2,4]triazol-1-ylethyli-
dene)amine (JP-A 79/119 462); cyazofamid,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonami-
de (CAS RN 120116-88-3]; benomyl,
N-butyl-2-acetylaminobenzoimidazol-1-carboxamide (U.S. Pat. No.
3,631,176); carbendazim, methyl (1H-benzoimidazol-2-yl)-carbamate
(U.S. Pat. No. 3,657,443); thiabendazole,
2-(1,3-thiazol-4-yl)benzimidazole (U.S. Pat. No. 3,017,415);
fuberidazole, 2-(2-furanyl)-1H-benzimidazole (DE 12 09 799);
ethaboxam,
N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolcarboxamide
(EP-A 639 574); etridiazole; hymexazole, 5-methyl-1,2-oxazol-3-ol
(JP 518249, JP 532202); azoxystrobin, methyl
2-{2-[6-(2-cyano-1-vinylpenta-1,3-dienyloxy)pyrimidin-4-yloxy]phenyl}-3-m-
ethoxyacrylate (EP-A 382 375); dimoxystrobin,
(E)-2-(methoxyimino)-N-methyl-2-[.alpha.-(2,5-xylyloxy)-o-tolyl]acetamide
(EP-A 477 631); fluoxastrobin,
(E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-
-1,4,2-dioxazin-3-yl)methanone O-methyloxime (WO 97/27189);
kresoxim-methyl, methyl
(E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate (EP-A 253
213); metominostrobin,
(E)-2-(methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide (EP-A
398 692); orysastrobin,
(2E)-2-(methoxyimino)-2-{2-[(3E,5E,6E)-5-(methoxyimino)-4,6-dimethyl-2,8--
dioxa-3,7-diazanona-3,6-dien-1-yl]phenyl}-N-methylacetamide (WO
97/15552); picoxystrobin, methyl
3-methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]acrylate
(EP-A 278 595); pyraclostrobin, methyl
N-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}(N-methoxy)carba-
mate (WO-A 96/01256); trifloxystrobin, methyl
(E)-methoxyimino-{(E)-.alpha.-[1-(.alpha.,.alpha.,.alpha.-trifluoro-m-tol-
yl)ethylideneaminooxy]-o-tolyl}acetate (EP-A 460 575); carboxin,
5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (U.S. Pat.
No. 3,249,499); benalaxyl, methyl
N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate (DE 29 03 612);
boscalid, 2-chloro-N-(4'-chlorbiphenyl-2-yl)nicotinamide (EP-A 545
099); fenhexamid,
N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide
(Proc. Br. Crop Prot. Conf.--Pests Dis., 1998, Vol. 2, p. 327);
flutolanil,.alpha.,.alpha.,.alpha.-trifluoro-3'-isopropoxy-o-toluanilide
(JP 1104514); furametpyr,
5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl)-1,3-dimethyl-1-
H-pyrazole-4-carboxamide [CAS RN 123572-88-3]; mepronil,
3'-isopropoxy-o-toluanilide (U.S. Pat. No. 3,937,840); metalaxyl,
methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (GB 15 00 581);
mefenoxam, methyl
N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate; ofurace,
(RS)-.alpha.-(2-chloro-N-2,6-xylylacetamido)-.gamma.-butyrolactone
[CAS RN 58810-48-3]; oxadixyl;
N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide
(GB 20 58 059); oxycarboxin,
5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide 4,4-dioxide (U.S.
Pat. No. 3,399,214); penthiopyrad,
N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyraz-
ole-4-carboxamide (JP 10130268); thifluzamide,
N-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-2-methyl-4-(trifluoromethyl)-5-
-thiazolecarboxamide; tiadinil,
3'-chloro-4,4'-dimethyl-1,2,3-thiadiazole-5-carboxanilide [CAS RN
223580-51-6]; dimethomorph,
3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylpropenone
(EP-A 120 321); flumorph,
3-(4-fluorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylpropenone
(EP-A 860 438); flumetover,
2-(3,4-dimethoxyphenyl)-N-ethyl-.alpha.,.alpha.,.alpha.-trifluoro-N-methy-
l-p-toluamide [AGROW No. 243, 22 (1995)]; fluopicolide
(picobenzamid),
2,6-dichloro-N-(3-chloro-5-trifluoromethylpyridin-2-ylmethyl)benzamide
(WO 99/42447); zoxamide,
(RS)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-p-toluamide
[CAS RN 156052-68-5]; carpropamid,
2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methyl-cyclopropanecar-
boxamide [CAS RN 104030-54-8]; diclocymet,
2-cyano-N-[(1R)-1-(2,4-dichlorophenyl)ethyl]-3,3-dimethyl
butanamide; mandipropamid,
(RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-
-2-ynyloxy)acetamide [CAS RN 374726-62-2]; fluazi nam,
3-chloro-N-[3-chloro-2,6-d
initro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine
(The Pesticide Manual, publ. The British Crop Protection Council,
10th ed. (1995), p. 474); pyrifenox,
1-(2,4-dichlorophenyl)-2-(3-pyridinyl)ethanone O-methyloxime (EP-A
49 854); bupirimate,
5-butyl-2-ethylamino-6-methyl-pyrimidin-4-yldimethylsulfamate [CAS
RN 41483-43-6]; cyprodinil,
(4-cyclopropyl-6-methylpyrimidin-2-yl)phenylamine (EP-A 310 550);
fenarimol, (4-chlorophenyl) (2-chlorophenyl)pyrimidin-5-ylmethanol
(GB 12 18 623); ferimzone, (Z)-2'-methylacetophenone
4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7];
mepanipyrim, (4-methyl-6-prop-1-ynylpyrimidin-2-yl)phenylamine
(EP-A 224 339); nuarimol,
.alpha.-(2-chlorophenyl)-.alpha.-(4-fluorophenyl)-5-pyrimidinem-
ethanol (GB 12 18 623); pyrimethanil,
4,6-dimethylpyrimidin-2-ylphenylamine (DD-A 151 404); triforine,
N,N-{piperazine-1,4-diylbis[(trichloromethyl)methylene]}diformamide
(DE 19 01 421); triazoxide,
7-chloro-3-imidazol-1-yl-1,2,4-benzotriazine-1-oxide [CAS-No.
72459-58-6]; fenpiclonil,
4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile (Proc. 1988 Br.
Crop Prot. Conf.--Pests Dis., Vol. 1, p. 65); fludioxonil,
4-(2,2-difluorobenzo[1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile
(The Pesticide Manual, publ. The British Crop Protection Council,
10th ed. (1995), p. 482); aldimorph, 4-alkyl-2,5 (or
2,6)-dimethylmorpholine, comprising 65-75% of
2,6-dimethylmorpholine and 25-35% of 2,5-dimethylmorpholine,
comprising more than 85% of 4-dodecyl-2,5 (or
2,6)-dimethylmorpholine, where "alkyl" may also include octyl,
decyl, tetradecyl or hexadecyl and where the cis/trans ratio is
1:1; dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE 1198125);
fenpropimorph,
(RS)-cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine
(DE 27 52 096); tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE
11 64 152); fenpropidin,
(RS)-1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine (DE 27 52
096); iprodione,
N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxamide
(GB 13 12 536); procymidone,
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide
(U.S. Pat. No. 3,903,090); vinclozolin,
3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (DE-OS
22 07 576); famoxadone,
(RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione;
fenamidone,
(S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one;
octhilinone; probenazole, 3-allyloxy-1,2-benzothiazole 1,1-dioxide;
amisulbrom,
N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazo-
le-1-sulfonamide (WO 03/053145); anilazine,
4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazine-2-amine (U.S. Pat.
No. 2,720,480); diclomezine,
6-(3,5-dichlorophenyl)-p-tolyl)pyridazin-3(2H)-one; pyroquilon;
proquinazid, 6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one (WO
97/48684); tricyclazole,
5-methyl-1,2,4-triazolo[3,4-b]benzothiazole (GB 14 19 121);
acibenzolar-S-methyl, methyl
benzo[1,2,3]thiadiazole-7-carbothionate; captafol,
N-(1,1,2,2-tetrachloroethylthio)cyclohex-4-ene-1,2-dicarboximid- e;
captan,
2-trichloromethylsulfanyl-3a,4,7,7a-tetrahydroisoindole-1,3-dio- ne
(U.S. Pat. No. 2,553,770); dazomet,
3,5-dimethyl-1,3,5-thiadiazinane-2-thione; folpet,
2-trichloromethylsulfanylisoindole-1,3-dione (U.S. Pat. No.
2,553,770); fenoxanil,
N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propanamide;
quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline (U.S. Pat.
No. 5,240,940); mancozeb, manganese ethylenebis(dithiocarbanate)
zinc complex (U.S. Pat. No. 3,379,610); maneb, manganese
ethylenebis(dithiocarbamate) (U.S. Pat. No. 2,504,404); metam,
methyldithiocarbaminic acid (U.S. Pat. No. 2,791,605); metiram,
zinc ammoniate ethylenebis(dithiocarbamate) (U.S. Pat. No.
3,248,400); propineb, zinc propylenebis(dithiocarbamate) polymer
(BE 611 960); ferbam, iron(3+) dimethyldithiocarbamate (U.S. Pat.
No. 1,972,961); thiram, bis(dimethylthiocarbamoyl)disulfide (DE 642
532); ziram, dimethyldithiocarbamate; zineb, zinc
ethylenebis(dithiocarbamate) (U.S. Pat. No. 2,457,674);
diethofencarb, isopropyl 3,4-diethoxycarbanilate; iprovalicarb,
isopropyl
[(1S)-2-methyl-1-(1-p-tolylethylcarbamoyl)propyl]carbamate (EP-A
472 996); flubenthiavalicarb (benthiavalicarb), isopropyl
{(S)-1-[(1R)-1-(6-fluorobenzothiazol-2-yl)ethylcarbamoyl]-2-methylpropyl}-
carbamate (JP-A 09/323,984); propamocarb, propyl
3-(dimethylamino)propylcarbamate (DE 16 43 040); dodine,
(2,4-dichlorophenoxy)acetic acid (U.S. Pat. No. 2,867,562);
iminoctadine, bis(8-guanidinooctyl)amine (GB 11 14 155); guazatine,
mixture of products from the amidation of
iminodi(octamethyllene)diamine, mainly iminoctadine; kasugamycin, 1
L-1,3,4/2,5,6-1-deoxy-2,3,4,5,6-pentahydroxycyclohexyl
2-amino-2,3,4,6-tetradeoxy-4-(.alpha.-iminoglycino)-.alpha.-D-arabinohexo-
pyranoside; streptomycin,
O-2-deoxy-2-methylamino-.alpha.-L-glucopyranosyl-(1.fwdarw.2)-O-5-deoxy-3-
-C-formyl-.alpha.-L-lyxofuranosyl-(1.fwdarw.4)
N.sup.1,N.sup.3-diamidino-D-streptamine; polyoxins,
5-(2-amino-5-O-carbamoyl-2-deoxy-L-xylonamido)-1-(5-carboxy-1,2,3,4-tetra-
hydro-2,4-dioxopyrimidin-1-yl)-1,5-dideoxy-.beta.-D-allofuranuronic
acid and the salts thereof; validamycin A, binapacryl,
(RS)-2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate; dinocap, the
mixture of 2,6-dinitro-4-octylphenyl crotonate and
2,4-dinitro-6-octylphenyl crotonate, wherein "octyl" is a mixture
of 1-methylheptyl, 1-ethylhexyl and 1-propylpentyl (U.S. Pat. No.
2,526,660); dinobuton, (RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl
carbonate; dithianon,
5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin-2,3-dicarbonitrile
(GB 857 383); isoprothiolane, indol-3-ylacetic acid; fentin
acetate, triphenyltin acetate (U.S. Pat. No. 3,499,086);
edifenphos, O-ethyl S,S-diphenyl phosphorodithioate; iprobenfos,
S-benzyl O,O-diisopropyl phosphorothioate (Jpn. Pesticide Inf., No.
2, S. 11 (1970)); fosetyl, fosetyl-aluminum, (aluminum)
ethylphosphonate (FR 22 54 276); pyrazophos, ethyl 2-d
iethoxyphosphinothioyloxy-5-methylpyrazolo[1,5-a]pyrimidine-6-c-
arboxylate (DE 15 45 790); tolclofos-methyl, O-2,6-dichloro-p-tolyl
O,O-dimethyl phosphorothioate (GB 14 67 561); chlorothalonil,
2,4,5,6-tetrachloroisophthalonitrile (U.S. Pat. No. 3,290,353);
dichlofluanid,
N-dichlorofluoromethylthio-N,N-dimethyl-N-phenylsulfamide (DE 11 93
498); flusulfamide,
2',4-dichloro-.alpha.,.alpha.,.alpha.-trifluoro-4'-nitro-m-toluenesulfani-
lide (EP-A 199 433); hexachlorobenzene (C. R. Seances Acad. Agric.
Fr., Vol. 31, p. 24 (1945)); phthalide (DE 16 43 347); pencycuron,
1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea (DE 27 32 257);
quintozene, pentachloronitrobenzene (DE 682 048);
thiophanate-methyl,
1,2-phenylenebis(iminocarbonothioyl)bis(dimethylcarbamate) (DE-OS
19 30 540); tolylfluanid,
N-dichlorofluoromethylthio-N,N-dimethyl-N-p-tolylsulfamide (DE 11
93 498); Bordeaux mixture, mixture of calcium hydroxide and
copper(II)
sulfate; copper hydroxide, Cu(OH).sub.2; copper oxychloride,
Cu.sub.2Cl(OH).sub.3; cyflufenamid,
(Z)-N-[.alpha.-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)-
benzyl]-2-phenylacetamide (WO 96/19442); cymoxanil,
1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea (U.S. Pat. No.
3,957,847); dimethirimol,
5-butyl-2-dimethylamino-6-methylpyrimidin-4-ol (GB 11 82 584);
ethirimol, 5-butyl-2-ethylamino-6-methylpyrimidin-4-ol (GB 11 82
584); furalaxyl, methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate (GB
14 48 810); metrafenone,
3'-bromo-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone (U.S. Pat.
No. 5,945,567); spiroxamine,
(8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)diethylamine (EP-A 281
842).
[0061] The compounds named according to IUPAC, their preparation
and their fungicidal activity are likewise known: methyl
(2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate,
methyl
(2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate
EP-A 12 01 648); methyl
2-(ortho-((2,5-dimethylphenyloxymethylene)phenyl)-3-methoxyacrylate
(EP-A 226 917);
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[-
1,2,4]triazolo[1,5-a]pyrimidine (WO 98/46608),
3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide (WO
99/24413),
N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-metha-
nesulfonylamino-3-methylbutyramide,
N-(2-{4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl}ethyl)-2-ethan-
esulfonylamino-3-methylbutyramide (WO 2004/049804),
N-(4'-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide-
,
N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(4'-chloro-3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5--
carboxamide,
N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide (WO 2003/066609);
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide (WO 2003/053145);
2-butoxy-6-iodo-3-propylchromen-4-one (WO 03/14103);
3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (EP-A
10 35 122); amisulbrom,
N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazo-
le-1-sulfonamide (WO 03/053145); methyl
3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)prop-
anoate (EP-A 1028125);
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne,
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine,
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine--
7-ylamine,
5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine, 6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine,
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine
and
5-trifluoromethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidi-
ne-7-ylamine are known from EP-A 71 792; EP-A 141 317; WO
2003/009687; WO 05/087771; WO 2005/087772; WO 2005/087773; WO
2006/087325; and/or WO 2006/092428;
N-(2',4'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',4'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',4'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',4'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(2',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide;
N-(3',5'-dichlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide,
N-(3',5'-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3',5'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(3'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide;
N-(3'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide;
N-(3'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide;
N-(3'-chlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4--
carboxamide;
N-(2'-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbo-
xamide;
N-(2'-chlorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole--
4-carboxamide;
N-(2'-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carbox-
amide;
N-(2'-chlorbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-c-
arboxamide;
N-(2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl)-1-methyl-3-trifluoromethyl-
-1H-pyrazole-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazol-
e-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide;
N-(2',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide;
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide;
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-
-pyrazole-4-carboxamide;
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide,
N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1-
H-pyrazole-4-carboxamide;
N-[2-(2-chlor-1,1,2-trifluoroethoxy)phenyl]-3-difluoromethyl-1-methyl-1H--
pyrazole-4-carboxamide;
4-carbonsaure-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-difluoromethyl-1--
methyl-1H-pyrazole-4-carboxamide;
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-pyr-
azole-4-carboxamide;
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-py-
razole-4-carboxamide; and
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-p-
yrazole-4-carboxamide are known from WO 2006/087343, WO 2001/42223,
WO 2005/34628, WO 2005/123689, WO 2005/123690, WO 2006/120219, WO
2007/017450, and/or EP Application No. 06123463.9.
[0062] It is an object of the present invention, with a view to
reducing the application rates and broadening the activity spectrum
of the known compounds, to provide mixtures which, at a reduced
total amount of active compounds applied, have improved activity
against pests.
[0063] One typical problem arising in the field of pest control
lies in the need to reduce the dosage rates of the active
ingredient in order to reduce or avoid unfavorable environmental or
toxicological effects whilst still allowing effective pest
control.
[0064] In regard to the instant invention the term pests embrace
animal pests, and harmful fungi.
[0065] Another problem encountered concerns the need to have
available pest control agents which are effective against a broad
spectrum of pests.
[0066] There also exists the need for pest control agents that
combine knock-down activity with prolonged control, that is, fast
action with long lasting action.
[0067] Another difficulty in relation to the use of pesticides is
that the repeated and exclusive application of an individual
pesticidal compound leads in many cases to a rapid selection of
pests, that means animal pests, and harmful fungi, which have
developed natural or adapted resistance against the active compound
in question. Therefore there is a need for pest control agents that
help prevent or overcome resistance.
[0068] It was therefore an object of the present invention to
provide pesticidal mixtures which solve the problems of reducing
the dosage rate and/or enhancing the spectrum of activity and/or
combining knock-down activity with prolonged control and/or to
resistance management.
[0069] We have found that this object is in part or in whole
achieved by the combination of active compounds defined at the
outset. Moreover, we have found that simultaneous, that is joint or
separate, application of a compound I and two or more compounds II
and III allows enhanced control of pests, that means animal pests,
and harmful fungi, compared to the control rates that are possible
with the individual compounds (synergistic mixtures).
[0070] In the definitions of the symbols given in formula I,
collective terms were used which are generally representative for
the following substituents:
alkyl: saturated straight-chain or branched hydrocarbon radicals
having 1 to 6, preferably up to 4 carbon atoms, for example
C.sub.1-C.sub.4-alkyl, such as methyl, ethyl, propyl,
1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,
1,1-dimethylethyl.
[0071] The formula I represents in particular compounds in which R
is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or
tert. butyl.
[0072] The formula I represents in particular compounds in which
B.sup.1 is chloro and cyano.
[0073] The formula I represents in particular compounds in which
B.sup.2 is bromo.
[0074] One embodiment represents compounds of formula I wherein R
is hydrogen. Another embodiment represents compounds of formula I
wherein R is C.sub.1-C.sub.4-alkyl.
[0075] In particular with a view to their use in the mixtures
according to the invention, preference is given to the compounds I
compiled in the table below.
TABLE-US-00001 TABLE I No. B.sup.1 B.sup.2 R I-1 H Br H I-2 CN Br H
I-3 Cl Br H I-4 H CF.sub.3 H I-5 CN CF.sub.3 H I-6 Cl CF.sub.3 H
I-7 H Br CH.sub.3 I-8 CN Br CH.sub.3 I-9 Cl Br CH.sub.3 I-10 H
CF.sub.3 CH.sub.3 I-11 CN CF.sub.3 CH.sub.3 I-12 Cl CF.sub.3
CH.sub.3 I-13 H Br CH.sub.2CH.sub.3 I-14 CN Br CH.sub.2CH.sub.3
I-15 Cl Br CH.sub.2CH.sub.3 I-16 H CF.sub.3 CH.sub.2CH.sub.3 I-17
CN CF.sub.3 CH.sub.2CH.sub.3 I-18 Cl CF.sub.3 CH.sub.2CH.sub.3 I-19
H Br CH.sub.2CH.sub.2CH.sub.3 I-20 CN Br CH.sub.2CH.sub.2CH.sub.3
I-21 Cl Br CH.sub.2CH.sub.2CH.sub.3 I-22 H CF.sub.3
CH.sub.2CH.sub.2CH.sub.3 I-23 CN CF.sub.3 CH.sub.2CH.sub.2CH.sub.3
I-24 Cl CF.sub.3 CH.sub.2CH.sub.2CH.sub.3 I-25 H Br
CH(CH.sub.3).sub.2 I-26 CN Br CH(CH.sub.3).sub.2 I-27 Cl Br
CH(CH.sub.3).sub.2 I-28 H CF.sub.3 CH(CH.sub.3).sub.2 I-29 CN
CF.sub.3 CH(CH.sub.3).sub.2 I-30 Cl CF.sub.3 CH(CH.sub.3).sub.2
[0076] Particular preference is given to the combinations of any
one of the compounds I-2, and I-3 with any one of the compounds II
and III as defined at the outset. Especially preferred is the
compound
I-3,3-bromo-4'-chloro-1-(3-chloro-2-pyridyl)-2'-methyl-6'-(methylcarbamoy-
l)pyrazole-5-carboxanilide, with the provisional ISO name
chlorantraniliprole.
##STR00003##
[0077] A preferred embodiment of the invention provides ternary
mixtures of a compound I, in particular of any one of compounds
I-2, and I-3 with a compound II, which is selected from the
groups:
azoles, in particular: cyazofamid, imazalil, pefurazoate,
prochloraz, triflumizole; strobilurines, in particular:
azoxystrobin, dimoxystrobin, enestroburin, metominostrobin,
orysastrobin; carboxamides, in particular: carpropamid, diclocymet,
flutolanil, furametpyr, mandipropamid, mepronil, metalaxyl,
mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad,
thifluzamide, tiadinil; heterocyclic compounds, in particular:
amisulbrom, anilazine, diclomezine, famoxadone, fenamidone,
octhilinone, probenazole, pyroquilon, proquinazid,
tricyclazole.
[0078] Another preferred embodiment of the invention provides
mixtures of azoxystrobin with any one of the compounds of formula I
compiled in table I.
[0079] Another preferred embodiment of the invention provides
mixtures of carpropamid with any one of the compounds of formula I
compiled in table I.
[0080] Another preferred embodiment of the invention provides
mixtures of diclozymet with any one of the compounds of formula I
compiled in table I.
[0081] Another preferred embodiment of the invention provides
mixtures of furametpyr with any one of the compounds of formula I
compiled in table I.
[0082] Another preferred embodiment of the invention provides
mixtures of orysastrobin with any one of the compounds of formula I
compiled in table I.
[0083] Another preferred embodiment of the invention provides
mixtures of probenazole with any one of the compounds of formula I
compiled in table I.
[0084] Another preferred embodiment of the invention provides
mixtures of thiadinil with any one of the compounds of formula I
compiled in table I.
[0085] Another preferred embodiment of the invention provides
mixtures of thifluzamide with any one of the compounds of formula I
compiled in table I.
[0086] Another preferred embodiment of the invention provides
mixtures of tricyclazole with any one of the compounds of formula I
compiled in table I.
[0087] Another preferred embodiment of the invention provides
mixtures of triflumizole with any one of the compounds of formula I
compiled in table I.
[0088] Another preferred embodiment of the invention provides
mixtures of pyroquilon with any one of the compounds of formula I
compiled in table I.
[0089] Another preferred embodiment of the invention provides
mixtures of dimoxystrobin with any one of the compounds of formula
I compiled in table I.
[0090] Another preferred embodiment of the invention provides
mixtures of fluoxastrobin with any one of the compounds of formula
I compiled in table I.
[0091] Another preferred embodiment of the invention provides
mixtures of picoxystrobin with any one of the compounds of formula
I compiled in table I.
[0092] Another preferred embodiment of the invention provides
mixtures of pyraclostrobin with any one of the compounds of formula
I compiled in table I.
[0093] Another preferred embodiment of the invention provides
mixtures of trifloxystrobin with any one of the compounds of
formula I compiled in table I.
[0094] Another preferred embodiment of the invention provides
mixtures of bitertanol with any one of the compounds of formula I
compiled in table I.
[0095] Another preferred embodiment of the invention provides
mixtures of cyproconazole with any one of the compounds of formula
I compiled in table I.
[0096] Another preferred embodiment of the invention provides
mixtures of epoxiconazole with any one of the compounds of formula
I compiled in table I.
[0097] Another preferred embodiment of the invention provides
mixtures of fluquinconazole with any one of the compounds of
formula I compiled in table I.
[0098] Another preferred embodiment of the invention provides
mixtures of flutriafol with any one of the compounds of formula I
compiled in table I.
[0099] Another preferred embodiment of the invention provides
mixtures of metconazole with any one of the compounds of formula I
compiled in table I.
[0100] Another preferred embodiment of the invention provides
mixtures of ipconazole with any one of the compounds of formula I
compiled in table I.
[0101] Another preferred embodiment of the invention provides
mixtures of prothioconazole with any one of the compounds of
formula I compiled in table I.
[0102] Another preferred embodiment of the invention provides
mixtures of prochloraz with any one of the compounds of formula I
compiled in table I.
[0103] Another preferred embodiment of the invention provides
mixtures of triadimenol with any one of the compounds of formula I
compiled in table I.
[0104] Another preferred embodiment of the invention provides
mixtures of tebuconazole with any one of the compounds of formula I
compiled in table I.
[0105] Another preferred embodiment of the invention provides
mixtures of difenoconazole with any one of the compounds of formula
I compiled in table I.
[0106] Another preferred embodiment of the invention provides
mixtures of thiabendazole with any one of the compounds of formula
I compiled in table I.
[0107] Another preferred embodiment of the invention provides
mixtures of propiconazole with any one of the compounds of formula
I compiled in table I.
[0108] Another preferred embodiment of the invention provides
mixtures of imazalil with any one of the compounds of formula I
compiled in table I.
[0109] Another preferred embodiment of the invention provides
mixtures of fludioxonil with any one of the compounds of formula I
compiled in table I.
[0110] Another preferred embodiment of the invention provides
mixtures of cyprodinil with any one of the compounds of formula I
compiled in table I.
[0111] Another preferred embodiment of the invention provides
mixtures of pyrimethanil with any one of the compounds of formula I
compiled in table I.
[0112] Another preferred embodiment of the invention provides
mixtures of guazatine with any one of the compounds of formula I
compiled in table I.
[0113] Another preferred embodiment of the invention provides
mixtures of dimethomorph with any one of the compounds of formula I
compiled in table I.
[0114] Another preferred embodiment of the invention provides
mixtures of fenpropimorph with any one of the compounds of formula
I compiled in table I.
[0115] Another preferred embodiment of the invention provides
mixtures of fenpropidin with any one of the compounds of formula I
compiled in table I.
[0116] Another preferred embodiment of the invention provides
mixtures of thiram with any one of the compounds of formula I
compiled in table I.
[0117] Another preferred embodiment of the invention provides
mixtures of captan with any one of the compounds of formula I
compiled in table I.
[0118] Another preferred embodiment of the invention provides
mixtures of metalaxyl with any one of the compounds of formula I
compiled in table I.
[0119] Another preferred embodiment of the invention provides
mixtures of mefenoxam with any one of the compounds of formula I
compiled in table I.
[0120] Another preferred embodiment of the invention provides
mixtures of thiophanat-methyl with any one of the compounds of
formula I compiled in table I.
[0121] Another preferred embodiment of the invention provides
mixtures of chlorothalonil with any one of the compounds of formula
I compiled in table I.
[0122] Another preferred embodiment of the invention provides
mixtures of carboxin with any one of the compounds of formula I
compiled in table I.
[0123] Another preferred embodiment of the invention provides
mixtures of boscalid with any one of the compounds of formula I
compiled in table I.
[0124] Another preferred embodiment of the invention provides
mixtures of ethaboxam with any one of the compounds of formula I
compiled in table I.
[0125] Another preferred embodiment of the invention provides
mixtures of
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide with any one of the compounds of formula I compiled
in table I.
[0126] Another preferred embodiment of the invention provides
mixtures of
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazol-
e-4-carboxamide with any one of the compounds of formula I compiled
in table I.
[0127] Another preferred embodiment of the invention provides
mixtures of
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide with any one of the compounds of formula I compiled
in table I.
[0128] Another preferred embodiment of the invention provides
mixtures of
N-(2',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide with any one of the compounds of formula I compiled
in table I.
[0129] Another preferred embodiment of the invention provides
mixtures of
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0130] Another preferred embodiment of the invention provides
mixtures of
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-
-pyrazole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0131] Another preferred embodiment of the invention provides
mixtures of
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0132] Another preferred embodiment of the invention provides
mixtures of
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-pyr-
azole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0133] Another preferred embodiment of the invention provides
mixtures of
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-py-
razole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0134] Another preferred embodiment of the invention provides
mixtures of
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-p-
yrazole-4-carboxamide with any one of the compounds of formula I
compiled in table I.
[0135] Another preferred embodiment of the invention provides
mixtures of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
[2-(1,2-dimethyl-propyl)-phenyl]-amide, with any one of the
compounds of formula I compiled in table I.
[0136] Another preferred embodiment of the invention provides
mixtures of
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine with any one of the compounds of formula I
compiled in table I.
[0137] Another preferred embodiment of the invention provides
mixtures of
6-(3,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamin-
e with any one of the compounds of formula I compiled in table
I.
[0138] Another preferred embodiment of the invention provides
mixtures of
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamin-
e with any one of the compounds of formula I compiled in table
I.
[0139] Another preferred embodiment of the invention provides
mixtures of
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine with any one of the compounds of formula I compiled in table
I.
[0140] Another preferred embodiment of the invention provides
mixtures of
5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine with
any one of the compounds of formula I compiled in table I.
[0141] Another preferred embodiment of the invention provides
mixtures of
6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine with
any one of the compounds of formula I compiled in table I.
[0142] Another preferred embodiment of the invention provides
mixtures of
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine with any
one of the compounds of formula I compiled in table I.
[0143] Another preferred embodiment of the invention provides
mixtures of
5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine with any
one of the compounds of formula I compiled in table I.
[0144] Another preferred embodiment of the invention provides
mixtures of
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine with any one of the compounds of formula I compiled in table
I.
[0145] Another preferred embodiment of the invention provides
mixtures of
6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine with
any one of the compounds of formula I compiled in table I.
[0146] Another preferred embodiment of the invention provides
mixtures of
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine
with any one of the compounds of formula I compiled in table I.
[0147] Another preferred embodiment of the invention provides
mixtures of
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine
with any one of the compounds of formula I compiled in table I.
[0148] Another preferred embodiment of the invention provides
mixtures of
5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimid-
ine-7-ylamine with any one of the compounds of formula I compiled
in table I.
[0149] Another preferred embodiment of the invention provides
mixtures of triazoxide with any one of the compounds of formula I
compiled in table I.
[0150] Preferred ternary mixtures, comprising a compound of formula
I as component 1, a fungicide II as component 2, and a further
fungicide as component 3, are compiled in following tables
Table 1
[0151] Combinations in which the component 1 is compound I-2, and
the combination of components 2 and 3 correspond for each ternary
combination to one row of Table A
Table 2
[0152] Combinations in which the component 1 is compound I-3, and
the combination of components 2 and 3 correspond for each ternary
combination to one row of Table A
[0153] Following abbreviations are used in Table A: [0154] B1:
N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide, [0155] B2:
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide; [0156] B3:
3,4-dichloro-N-(2-cyanophenyl)isothiazol-5-carboxamide; [0157] B4:
N-(3',5'-difluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4--
carboxamide; [0158] B5:
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazol-
e-4-carboxamide; [0159] B6:
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide; [0160] B7:
N-(2',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide; [0161] B8:
N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide; [0162] B9:
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide, [0163] B10:
N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-methyl-3-trifluoromethyl-1H-pyr-
azole-4-carboxamide; [0164] B11:
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-py-
razole-4-carboxamide; [0165] B12:
N-(4'-(trifluoromethylthio)biphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-p-
yrazole-4-carboxamide; [0166] B13:
5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
[2-(1,2-dimethyl-propyl)-phenyl]-amide; [0167] B14:
5-chloro-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluoro-phenyl)-[1,2,4]tr-
iazolo[1,5-a]pyrimidine; [0168] B15:
6-(3,4-dichloro-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylami-
ne; [0169] B16:
6-(4-tert-butylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamin-
e; [0170] B17:
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-yla-
mine; [0171] B18:
5-methyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine; [0172]
B19: 6-methyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine;
[0173] B20:
6-ethyl-5-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine; [0174]
B21: 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine;
[0175] B22:
5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylam-
ine; [0176] B23:
6-octyl-5-propyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine; [0177]
B24:
5-methoxymethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine;
[0178] B25:
6-octyl-5-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine;
[0179] B26:
5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1,2,4]triazolo[1,5-a]pyrimid-
ine-7-ylamine.
TABLE-US-00002 [0179] TABLE A No. Component 2 Component 3 A-1
difenoconazole cyproconazole A-2 difenoconazole ipconazole A-3
difenoconazole metconazole A-4 difenoconazole triazoxide A-5
difenoconazole triticonazole A-6 difenoconazole azoxystrobin A-7
difenoconazole dimoxystrobin A-8 difenoconazole fluoxastrobin A-9
difenoconazole kresoxim-methyl A-10 difenoconazole metominostrobin
A-11 difenoconazole orysastrobin A-12 difenoconazole picoxystrobin
A-13 difenoconazole pyraclostrobin A-14 difenoconazole
trifloxystrobin A-15 difenoconazole carboxin A-16 difenoconazole
boscalid A-17 difenoconazole B1 A-18 difenoconazole B2 A-19
difenoconazole B3 A-20 difenoconazole B4 A-21 difenoconazole B5
A-22 difenoconazole B6 A-23 difenoconazole B7 A-24 difenoconazole
B8 A-25 difenoconazole B9 A-26 difenoconazole B10 A-27
difenoconazole B11 A-28 difenoconazole B12 A-29 difenoconazole B13
A-30 difenoconazole mefenoxam A-31 difenoconazole mancozeb A-32
difenoconazole maneb A-33 difenoconazole metiram A-34
difenoconazole propineb A-35 difenoconazole thiram A-36
difenoconazole zineb A-37 difenoconazole ziram A-38 epoxiconazole
iprodione A-39 epoxiconazole prochloraze A-40 epoxiconazole
pyrimethanil A-41 epoxiconazole triazoxide A-42 epoxiconazole
azoxystrobin A-43 epoxiconazole dimoxystrobin A-44 epoxiconazole
fluoxastrobin A-45 epoxiconazole kresoxim-methyl A-46 epoxiconazole
metominostrobin A-47 epoxiconazole orysastrobin A-48 epoxiconazole
picoxystrobin A-49 epoxiconazole pyraclostrobin A-50 epoxiconazole
trifloxystrobin A-51 epoxiconazole boscalid A-52 epoxiconazole B1
A-53 epoxiconazole B2 A-54 epoxiconazole B3 A-55 epoxiconazole B4
A-56 epoxiconazole B5 A-57 epoxiconazole B6 A-58 epoxiconazole B7
A-59 epoxiconazole B8 A-60 epoxiconazole B9 A-61 epoxiconazole B10
A-62 epoxiconazole B11 A-63 epoxiconazole B12 A-64 epoxiconazole
B13 A-65 epoxiconazole B14 A-66 epoxiconazole B15 A-67
epoxiconazole B16 A-68 epoxiconazole B17 A-69 epoxiconazole B18
A-70 epoxiconazole B19 A-71 epoxiconazole B20 A-72 epoxiconazole
B21 A-73 epoxiconazole B22 A-74 epoxiconazole B23 A-75
epoxiconazole B24 A-76 epoxiconazole B25 A-77 epoxiconazole B26
A-78 epoxiconazole mancozeb A-79 epoxiconazole maneb A-80
epoxiconazole metiram A-81 epoxiconazole propineb A-82
epoxiconazole thiram A-83 epoxiconazole zineb A-84 epoxiconazole
ziram A-85 fluquinconazole azoxystrobin A-86 fluquinconazole
dimoxystrobin A-87 fluquinconazole fluoxastrobin A-88
fluquinconazole kresoxim-methyl A-89 fluquinconazole
metominostrobin A-90 fluquinconazole orysastrobin A-91
fluquinconazole picoxystrobin A-92 fluquinconazole pyraclostrobin
A-93 fluquinconazole trifloxystrobin A-94 fluquinconazole
prochloraz A-95 fluquinconazole triazoxide A-96 fluquinconazole
boscalid A-97 fluquinconazole B1 A-98 fluquinconazole B2 A-99
fluquinconazole B3 A-100 fluquinconazole B4 A-101 fluquinconazole
B5 A-102 fluquinconazole B6 A-103 fluquinconazole B7 A-104
fluquinconazole B8 A-105 fluquinconazole B9 A-106 fluquinconazole
B10 A-107 fluquinconazole B11 A-108 fluquinconazole B12 A-109
fluquinconazole B13 A-110 fluquinconazole B14 A-111 fluquinconazole
B15 A-112 fluquinconazole B16 A-113 fluquinconazole B17 A-114
fluquinconazole B18 A-115 fluquinconazole B19 A-116 fluquinconazole
B20 A-117 fluquinconazole B21 A-118 fluquinconazole B22 A-119
fluquinconazole B23 A-120 fluquinconazole B24 A-121 fluquinconazole
B25 A-122 fluquinconazole B26 A-123 metconazole boscalid A-124
metconazole B1 A-125 metconazole B2 A-126 metconazole B3 A-127
metconazole B4 A-128 metconazole B5 A-129 metconazole B6 A-130
metconazole B7 A-131 metconazole B8 A-132 metconazole B9 A-133
metconazole B10 A-134 metconazole B11 A-135 metconazole B12 A-136
metconazole B13 A-137 metconazole B14 A-138 prochloraz metalaxyl
A-139 prochloraz triticonazole A-140 prochloraz ipconazole A-141
prochloraz metconazole A-142 prothioconazole azoxystrobin A-143
prothioconazole dimoxystrobin A-144 prothioconazole fluoxastrobin
A-145 prothioconazole kresoxim-methyl A-146 prothioconazole
metominostrobin A-147 prothioconazole orysastrobin A-148
prothioconazole picoxystrobin A-149 prothioconazole pyraclostrobin
A-150 prothioconazole trifloxystrobin A-151 prothioconazole
ipconazole A-152 prothioconazole metconazole A-153 prothioconazole
prochloraze A-154 prothioconazole tebuconazole A-155
prothioconazole triazoxide A-156 prothioconazole triticonazole
A-157 prothioconazole metalaxyl A-158 prothioconazole mancozeb
A-159 prothioconazole maneb A-160 prothioconazole metiram A-161
prothioconazole propineb A-162 prothioconazole thiram A-163
prothioconazole zineb A-164 prothioconazole ziram A-165
prothioconazole boscalid A-166 prothioconazole B1 A-167
prothioconazole B2 A-168 prothioconazole B3 A-169 prothioconazole
B4 A-170 prothioconazole B5 A-171 prothioconazole B6 A-172
prothioconazole B7 A-173 prothioconazole B8 A-174 prothioconazole
B9 A-175 prothioconazole B10 A-176 prothioconazole B11 A-177
prothioconazole B12 A-178 prothioconazole B13 A-179 tebuconazole
azoxystrobin A-180 tebuconazole dimoxystrobin A-181 tebuconazole
fluoxastrobin A-182 tebuconazole kresoxim-methyl A-183 tebuconazole
metominostrobin A-184 tebuconazole orysastrobin A-185 tebuconazole
picoxystrobin A-186 tebuconazole pyraclostrobin A-187 tebuconazole
trifloxystrobin A-188 tebuconazole prochloraze A-189 tebuconazole
triazoxide A-190 tebuconazole mancozeb A-191 tebuconazole maneb
A-192 tebuconazole metiram A-193 tebuconazole propineb A-194
tebuconazole thiram A-195 tebuconazole zineb A-196 tebuconazole
ziram A-197 triticonazole epoxiconazole A-198 triticonazole
prochloraze A-199 triticonazole triazoxide A-200 triticonazole
iprodione A-201 triticonazole pyrimethanil A-202 triticonazole
azoxystrobin A-203 triticonazole dimoxystrobin A-204 triticonazole
fluoxastrobin A-205 triticonazole kresoxim-methyl A-206
triticonazole metominostrobin A-207 triticonazole orysastrobin
A-208 triticonazole picoxystrobin A-209 triticonazole
pyraclostrobin A-210 triticonazole trifloxystrobin A-211
triticonazole Metalaxyl A-212 triticonazole mancozeb A-213
triticonazole maneb A-214 triticonazole metiram A-215 triticonazole
propineb A-216 triticonazole thiram A-217 triticonazole zineb A-218
triticonazole ziram A-219 triticonazole boscalid A-220
triticonazole B1 A-221 triticonazole B2 A-222 triticonazole B3
A-223 triticonazole B4 A-224 triticonazole B5 A-225 triticonazole
B6 A-226 triticonazole B7 A-227 triticonazole B8 A-228
triticonazole B9 A-229 triticonazole B10 A-230 triticonazole B11
A-231 triticonazole B12 A-232 triticonazole B13 A-233 triticonazole
B14 A-234 triticonazole B15 A-235 triticonazole B16 A-236
triticonazole B17 A-237 triticonazole B18 A-238 triticonazole B19
A-239 triticonazole B20 A-240 triticonazole B21 A-241 triticonazole
B22 A-242 triticonazole B23 A-243 triticonazole B24 A-244
triticonazole B25 A-245 triticonazole B26 A-246 triazoxide B1
A-247 triazoxide B2 A-248 triazoxide B3 A-249 azoxystrobin boscalid
A-250 dimoxystrobin boscalid A-251 fluoxastrobin boscalid A-252
kresoxim-methyl boscalid A-253 metominostrobin boscalid A-254
orysastrobin boscalid A-255 picoxystrobin boscalid A-256
pyraclostrobin boscalid A-257 trifloxystrobin boscalid A-258
azoxystrobin B1 A-259 dimoxystrobin B1 A-260 fluoxastrobin B1 A-261
kresoxim-methyl B1 A-262 metominostrobin B1 A-263 orysastrobin B1
A-264 picoxystrobin B1 A-265 pyraclostrobin B1 A-266
trifloxystrobin B1 A-267 azoxystrobin B2 A-268 dimoxystrobin B2
A-269 fluoxastrobin B2 A-270 kresoxim-methyl B2 A-271
metominostrobin B2 A-272 orysastrobin B2 A-273 picoxystrobin B2
A-274 pyraclostrobin B2 A-275 trifloxystrobin B2 A-276 azoxystrobin
B3 A-277 dimoxystrobin B3 A-278 fluoxastrobin B3 A-279
kresoxim-methyl B3 A-280 metominostrobin B3 A-281 orysastrobin B3
A-282 picoxystrobin B3 A-283 pyraclostrobin B3 A-284
trifloxystrobin B3 A-285 azoxystrobin B4 A-286 dimoxystrobin B4
A-287 fluoxastrobin B4 A-288 kresoxim-methyl B4 A-289
metominostrobin B4 A-290 orysastrobin B4 A-291 picoxystrobin B4
A-292 pyraclostrobin B4 A-293 trifloxystrobin B4 A-294 azoxystrobin
B5 A-295 dimoxystrobin B5 A-296 fluoxastrobin B5 A-297
kresoxim-methyl B5 A-298 metominostrobin B5 A-299 orysastrobin B5
A-300 picoxystrobin B5 A-301 pyraclostrobin B5 A-302
trifloxystrobin B5 A-303 azoxystrobin B6 A-304 dimoxystrobin B6
A-305 fluoxastrobin B6 A-306 kresoxim-methyl B6 A-307
metominostrobin B6 A-308 orysastrobin B6 A-309 picoxystrobin B6
A-310 pyraclostrobin B6 A-311 trifloxystrobin B6 A-312 azoxystrobin
B7 A-313 dimoxystrobin B7 A-314 fluoxastrobin B7 A-315
kresoxim-methyl B7 A-316 metominostrobin B7 A-317 orysastrobin B7
A-318 picoxystrobin B7 A-319 pyraclostrobin B7 A-320
trifloxystrobin B7 A-321 azoxystrobin B8 A-322 dimoxystrobin B8
A-323 fluoxastrobin B8 A-324 kresoxim-methyl B8 A-325
metominostrobin B8 A-326 orysastrobin B8 A-327 picoxystrobin B8
A-328 pyraclostrobin B8 A-329 trifloxystrobin B8 A-330 azoxystrobin
B9 A-331 dimoxystrobin B9 A-332 fluoxastrobin B9 A-333
kresoxim-methyl B9 A-334 metominostrobin B9 A-335 orysastrobin B9
A-336 picoxystrobin B9 A-337 pyraclostrobin B9 A-338
trifloxystrobin B9 A-339 azoxystrobin B10 A-340 dimoxystrobin B10
A-341 fluoxastrobin B10 A-342 kresoxim-methyl B10 A-343
metominostrobin B10 A-344 orysastrobin B10 A-345 picoxystrobin B10
A-346 pyraclostrobin B10 A-347 trifloxystrobin B10 A-348
azoxystrobin B11 A-349 dimoxystrobin B11 A-350 fluoxastrobin B11
A-351 kresoxim-methyl B11 A-352 metominostrobin B11 A-353
orysastrobin B11 A-354 picoxystrobin B11 A-355 pyraclostrobin B11
A-356 trifloxystrobin B11 A-357 azoxystrobin B12 A-358
dimoxystrobin B12 A-359 fluoxastrobin B12 A-360 kresoxim-methyl B12
A-361 metominostrobin B12 A-362 orysastrobin B12 A-363
picoxystrobin B12 A-364 pyraclostrobin B12 A-365 trifloxystrobin
B12 A-366 azoxystrobin B13 A-367 dimoxystrobin B13 A-368
fluoxastrobin B13 A-369 kresoxim-methyl B13 A-370 metominostrobin
B13 A-371 orysastrobin B13 A-372 picoxystrobin B13 A-373
pyraclostrobin B13 A-374 trifloxystrobin B13 A-375 azoxystrobin B14
A-376 dimoxystrobin B14 A-377 fluoxastrobin B14 A-378
kresoxim-methyl B14 A-379 metominostrobin B14 A-380 orysastrobin
B14 A-381 picoxystrobin B14 A-382 pyraclostrobin B14 A-383
trifloxystrobin B14 A-384 azoxystrobin B15 A-385 dimoxystrobin B15
A-386 fluoxastrobin B15 A-387 kresoxim-methyl B15 A-388
metominostrobin B15 A-389 orysastrobin B15 A-390 picoxystrobin B15
A-391 pyraclostrobin B15 A-392 trifloxystrobin B15 A-393
azoxystrobin B16 A-394 dimoxystrobin B16 A-395 fluoxastrobin B16
A-396 kresoxim-methyl B16 A-397 metominostrobin B16 A-398
orysastrobin B16 A-399 picoxystrobin B16 A-400 pyraclostrobin B16
A-401 trifloxystrobin B16 A-402 azoxystrobin B17 A-403
dimoxystrobin B17 A-404 fluoxastrobin B17 A-405 kresoxim-methyl B17
A-406 orysastrobin B17 A-407 metominostrobin B17 A-408
picoxystrobin B17 A-409 pyraclostrobin B17 A-410 trifloxystrobin
B17 A-411 azoxystrobin B18 A-412 dimoxystrobin B18 A-413
fluoxastrobin B18 A-414 kresoxim-methyl B18 A-415 metominostrobin
B18 A-416 orysastrobin B18 A-417 picoxystrobin B18 A-418
pyraclostrobin B18 A-419 trifloxystrobin B18 A-420 azoxystrobin B19
A-421 dimoxystrobin B19 A-422 fluoxastrobin B19 A-423
kresoxim-methyl B19 A-424 metominostrobin B19 A-425 orysastrobin
B19 A-426 picoxystrobin B19 A-427 pyraclostrobin B19 A-428
trifloxystrobin B19 A-429 azoxystrobin B20 A-430 dimoxystrobin B20
A-431 fluoxastrobin B20 A-432 kresoxim-methyl B20 A-433
metominostrobin B20 A-434 orysastrobin B20 A-435 picoxystrobin B20
A-436 pyraclostrobin B20 A-437 trifloxystrobin B20 A-438
azoxystrobin B21 A-439 dimoxystrobin B21 A-440 fluoxastrobin B21
A-441 kresoxim-methyl B21 A-442 metominostrobin B21 A-443
orysastrobin B21 A-444 picoxystrobin B21 A-445 pyraclostrobin B21
A-446 trifloxystrobin B21 A-447 azoxystrobin B22 A-448
dimoxystrobin B22 A-449 fluoxastrobin B22 A-450 kresoxim-methyl B22
A-451 metominostrobin B22 A-452 orysastrobin B22 A-453
picoxystrobin B22 A-454 pyraclostrobin B22 A-455 trifloxystrobin
B22 A-456 azoxystrobin B23 A-457 dimoxystrobin B23 A-458
fluoxastrobin B23 A-459 kresoxim-methyl B23 A-460 metominostrobin
B23 A-461 orysastrobin B23 A-462 picoxystrobin B23 A-463
pyraclostrobin B23 A-464 trifloxystrobin B23 A-465 azoxystrobin B24
A-466 dimoxystrobin B24 A-467 fluoxastrobin B24 A-468
kresoxim-methyl B24 A-469 metominostrobin B24 A-470 orysastrobin
B24 A-471 picoxystrobin B24 A-472 pyraclostrobin B24 A-473
trifloxystrobin B24 A-474 azoxystrobin B25 A-475 dimoxystrobin B25
A-476 fluoxastrobin B25 A-477 kresoxim-methyl B25 A-478
metominostrobin B25 A-479 orysastrobin B25 A-480 picoxystrobin B25
A-481 pyraclostrobin B25 A-482 trifloxystrobin B25 A-483
azoxystrobin B26 A-484 dimoxystrobin B26 A-485 fluoxastrobin B26
A-486 kresoxim-methyl B26 A-487 metominostrobin B26 A-488
orysastrobin B26 A-489 picoxystrobin B26 A-490 pyraclostrobin B26
A-491 trifloxystrobin B26 A-492 azoxystrobin captan A-493
dimoxystrobin captan A-494 fluoxastrobin captan A-495
kresoxim-methyl captan A-496 metominostrobin captan A-497
orysastrobin captan
A-498 picoxystrobin captan A-499 pyraclostrobin captan A-500
trifloxystrobin captan A-501 azoxystrobin folpet A-502
dimoxystrobin folpet A-503 fluoxastrobin folpet A-504
kresoxim-methyl folpet A-505 metominostrobin folpet A-506
orysastrobin folpet A-507 picoxystrobin folpet A-508 pyraclostrobin
folpet A-509 trifloxystrobin folpet A-510 azoxystrobin metalaxyl
A-511 dimoxystrobin metalaxyl A-512 fluoxastrobin metalaxyl A-513
kresoxim-methyl metalaxyl A-514 metominostrobin metalaxyl A-515
orysastrobin metalaxyl A-516 picoxystrobin metalaxyl A-517
pyraclostrobin metalaxyl A-518 trifloxystrobin metalaxyl A-519
azoxystrobin mefenoxam A-520 dimoxystrobin mefenoxam A-521
fluoxastrobin mefenoxam A-522 kresoxim-methyl mefenoxam A-523
metominostrobin mefenoxam A-524 orysastrobin mefenoxam A-525
picoxystrobin mefenoxam A-526 pyraclostrobin mefenoxam A-527
trifloxystrobin mefenoxam A-528 azoxystrobin dimethomorph A-529
dimoxystrobin dimethomorph A-530 fluoxastrobin dimethomorph A-531
kresoxim-methyl dimethomorph A-532 metominostrobin dimethomorph
A-533 orysastrobin dimethomorph A-534 picoxystrobin dimethomorph
A-535 pyraclostrobin dimethomorph A-536 trifloxystrobin
dimethomorph A-537 azoxystrobin thiophanate-methyl A-538
dimoxystrobin thiophanate-methyl A-539 fluoxastrobin
thiophanate-methyl A-540 kresoxim-methyl thiophanate-methyl A-541
metominostrobin thiophanate-methyl A-542 orysastrobin
thiophanate-methyl A-543 picoxystrobin thiophanate-methyl A-544
pyraclostrobin thiophanate-methyl A-545 trifloxystrobin
thiophanate-methyl A-546 metalaxyl boscalid A-547 metalaxyl B1
A-548 metalaxyl B2 A-549 metalaxyl B3 A-550 metalaxyl B4 A-551
metalaxyl B5 A-552 metalaxyl B6 A-553 metalaxyl B7 A-554 metalaxyl
B8 A-555 metalaxyl B9 A-556 metalaxyl B10 A-557 metalaxyl B11 A-558
metalaxyl B12 A-559 metalaxyl B13 A-560 metalaxyl B14 A-561
mefenoxam boscalid A-562 mefenoxam B1 A-563 mefenoxam B2 A-564
mefenoxam B3 A-565 mefenoxam B4 A-566 mefenoxam B5 A-567 mefenoxam
B6 A-568 mefenoxam B7 A-569 mefenoxam B8 A-570 mefenoxam B9 A-571
mefenoxam B10 A-572 mefenoxam B11 A-573 mefenoxam B12 A-574
mefenoxam B13 A-575 guazatine epoxiconazole A-576 guazatine
difenoconazole A-577 guazatine metconazole A-578 guazatine
tebuconazole A-579 guazatine triticonazole A-580 guazatine carboxin
A-581 thiophanate-methyl epoxiconazole A-582 thiophanate-methyl
difenoconazole A-583 thiophanate-methyl metconazole A-584
thiophanate-methyl tebuconazole A-585 thiophanate-methyl
triticonazole A-586 thiophanate-methyl carboxin A-587 captan
epoxiconazole A-588 captan difenoconazole A-589 captan metconazole
A-590 captan tebuconazole A-591 captan triticonazole A-592 captan
carboxin A-593 folpet epoxiconazole A-594 folpet difenoconazole
A-595 folpet metconazole A-596 folpet tebuconazole A-597 folpet
triticonazole A-598 folpet carboxin A-599 fludioxionil
difenoconazole A-600 fludioxionil flutriafol A-601 fludioxionil
ipconazole A-602 fludioxionil metconazole A-603 fludioxionil
tebuconazole A-604 fludioxionil triticonazole A-605 fludioxionil
azoxystrobin A-606 fludioxionil dimoxystrobin A-607 fludioxionil
fluoxastrobin A-608 fludioxionil kresoxim-methyl A-609 fludioxionil
metominostrobin A-610 fludioxionil orysastrobin A-611 fludioxionil
picoxystrobin A-612 fludioxionil pyraclostrobin A-613 fludioxionil
trifloxystrobin A-614 fludioxionil carboxine A-615 fludioxionil
cyprodinil A-616 fludioxionil mefenoxam A-617 fludioxionil boscalid
A-618 fludioxionil B1 A-619 fludioxionil B2 A-620 fludioxionil B3
A-621 fludioxionil B4 A-622 fludioxionil B5 A-623 fludioxionil B6
A-624 fludioxionil B7 A-625 fludioxionil B8 A-626 fludioxionil B9
A-627 fludioxionil B10 A-628 fludioxionil B11 A-629 fludioxionil
B12 A-630 fludioxionil B13
[0180] For use according to the present invention, the mixtures
according to the invention, or the compound I and the active
compounds II and III, can be converted into the customary
formulations, for example solutions, emulsions, suspensions, dusts,
powders, pastes and granules. The use form depends on the
particular intended purpose; in each case, it should ensure a fine
and even distribution of the compound according to the
invention.
[0181] The formulations are prepared in a known manner, for example
by extending the active compound with solvents and/or carriers, if
desired using emulsifiers and dispersants. Solvents/auxiliaries
which are suitable are essentially: [0182] water, aromatic solvents
(for example Solvesso products, xylene), paraffins (for example
mineral oil fractions), alcohols (for example methanol, butanol,
pentanol, benzyl alcohol), ketones (for example cyclohexanone,
gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol
diacetate), glycols, fatty acid dimethylamides, fatty acids and
fatty acid esters. In principle, solvent mixtures may also be used,
[0183] carriers such as ground natural minerals (for example
kaolins, clays, talc, chalk) and ground synthetic minerals (for
example highly disperse silica, silicates); emulsifiers such as
nonionic and anionic emulsifiers (for example polyoxyethylene fatty
alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants
such as lignosulfite waste liquors and methylcellulose.
[0184] Suitable surfactants are alkali metal, alkaline earth metal
and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid,
phenolsulfonic acid, dibutylnaphthalenesulfonic acid,
alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol
sulfates, fatty acids and sulfated fatty alcohol glycol ethers,
furthermore condensates of sulfonated naphthalene and naphthalene
derivatives with formaldehyde, condensates of naphthalene or of
naphthalenesulfonic acid with phenol and formaldehyde,
polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol,
octylphenol, nonylphenol, alkylphenol polyglycol ethers,
tributylphenyl polyglycol ethers, tristearylphenyl polyglycol
ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol
ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene
alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol
polyglycol ether acetal, sorbitol esters, lignosulfite waste
liquors and methylcellulose.
[0185] Suitable for the preparation of directly sprayable
solutions, emulsions, pastes or oil dispersions are mineral oil
fractions of medium to high boiling point, such as kerosene or
diesel oil, furthermore coal tar oils and oils of vegetable or
animal origin, aliphatic, cyclic and aromatic hydrocarbons, for
example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
naphthalenes or their derivatives, methanol, ethanol, propanol,
butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar
solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and
water.
[0186] Also anti-freezing agents such as glycerin, ethylene glycol,
propylene glycol and bactericides such as can be added to the
formulation.
[0187] Suitable antifoaming agents are for example antifoaming
agents based on silicon or magnesium stearate.
[0188] Suitable preservatives are for example Dichlorophen and
enzylalkoholhemiformal. Seed Treatment formulations may
additionally comprise binders and optionally colorants.
[0189] Binders can be added to improve the adhesion of the active
materials on the seeds after treatment. Suitable binders are block
copolymers EO/PO surfactants but also polyvinyl alcohols,
polyvinylpyrrolidones, polyacrylates, polymethacrylates,
polybutenes, polyisoutylenes, polystyrene, polyethyleneamines,
polyethyleneamides, polyethyleneimines (Lupasol.RTM.,
Polymin.RTM.), polyethers, polyurethans, polyvinylacetate, tylose
and copolymers derived from these polymers.
[0190] Optionally, also colorants can be included in the
formulation. Suitable colorants or dyes for seed treatment
formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red
1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment
blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,
pigment red 112, pigment red 48:2, pigment red 48:1, pigment red
57:1, pigment red 53:1, pigment orange 43, pigment orange 34,
pigment orange 5, pigment green 36, pigment green 7, pigment white
6, pigment brown 25, basic violet 10, basic violet 49, acid red 51,
acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red
10, basic red 108.
[0191] Examples of a gelling agent is carrageen (Satiagel.RTM.)
[0192] Powders, materials for spreading and dustable products can
be prepared by mixing or concomitantly grinding the active
substances with a solid carrier.
[0193] Granules, for example coated granules, impregnated granules
and homogeneous granules, can be prepared by binding the active
compounds to solid carriers. Examples of solid carriers are mineral
earths such as silica gels, silicates, talc, kaolin, attaclay,
limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous
earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground
synthetic materials, fertilizers, such as, for example, 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 and other solid carriers.
[0194] In general, the formulations comprise from 0.01 to 95% by
weight, preferably from 0.1 to 90% by weight, of the active
compound. The active compounds are employed in a purity of from 90%
to 100%, preferably 95% to 100% (according to NMR spectrum).
[0195] For seed treatment purposes, respective formulations can be
diluted 2-10 fold leading to concentrations in the ready to use
preparations of 0.01 to 60% by weight active compound by weight,
preferably 0.1 to 40% by weight.
[0196] The following are examples of formulations: 1. Products for
dilution with water For seed treatment purposes, such products may
be applied to the seed diluted or undiluted.
A Water-Soluble Concentrates (SL, LS)
[0197] 10 parts by weight of the active compounds are dissolved
with 90 parts by weight of water or a water-soluble solvent. As an
alternative, wetters or other auxiliaries are added. The active
compound dissolves upon dilution with water. A formulation having
an active compound content of 10% by weight is obtained in this
manner.
B Dispersible concentrates (DC)
[0198] 20 parts by weight of the active compounds are dissolved in
70 parts by weight of cyclohexanone with addition of 10 parts by
weight of a dispersant, for example polyvinylpyrrolidone. Dilution
with water gives a dispersion. The active compound content is 20%
by weight
C Emulsifiable Concentrates (EC)
[0199] 15 parts by weight of the active compounds are dissolved in
75 parts by weight of xylene with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5
parts by weight). Dilution with water gives an emulsion. The
formulation has an active compound content of 15% by weight.
D Emulsions (EW, EO, ES)
[0200] 25 parts by weight of the active compounds are dissolved in
35 parts by weight of xylene with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5
parts by weight). This mixture is added into 30 parts by weight of
water by means of an emulsifying machine (e.g. Ultraturrax) and
made into a homogeneous emulsion. Dilution with water gives an
emulsion. The formulation has an active compound content of 25% by
weight.
E Suspensions (SC, OD, FS)
[0201] In an agitated ball mill, 20 parts by weight of the active
compounds are comminuted with addition of 10 parts by weight of
dispersants and wetters and 70 parts by weight of water or an
organic solvent to give a fine active compound suspension. Dilution
with water gives a stable suspension of the active compound. The
active compound content in the formulation is 20% by weight.
F Water-Dispersible Granules and Water-Soluble Granules (WG,
SG)
[0202] 50 parts by weight of the active compounds are ground finely
with addition of 50 parts by weight of dispersants and wetters and
made into water-dispersible or water-soluble granules by means of
technical appliances (for example extrusion, spray tower, fluidized
bed). Dilution with water gives a stable dispersion or solution of
the active compound. The formulation has an active compound content
of 50% by weight.
G Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS,
WS)
[0203] 75 parts by weight of the active compounds are ground in a
rotor-stator mill with addition of 25 parts by weight of
dispersants and wetters as well as silica gel. Dilution with water
gives a stable dispersion or solution of the active compound. The
active compound content of the formulation is 75% by weight.
H Gel formulations (GF)
[0204] In a ball mill, 20 parts by weight of the active compounds,
10 parts by weight of dispersant, 1 part by weight of gelling agent
and 70 parts by weight of water or an organic solvent are ground to
give a fine suspension. On dilution with water, a stable suspension
having an active compound content of 20% by weight is obtained.
2. Products to be Applied Undiluted
[0205] I Dustable powders (DP, DS)
[0206] 5 parts by weight of the active compounds are ground finely
and mixed intimately with 95 parts by weight of finely divided
kaolin. This gives a dustable product having an active compound
content of 5% by weight.
J Granules (GR, FG, GG, MG)
[0207] 0.5 part by weight of the active compounds is ground finely
and associated with 99.5 parts by weight of carriers. Current
methods are extrusion, spray-drying or the fluidized bed. This
gives granules to be applied undiluted having an active compound
content of 0.5% by weight.
K ULV Solutions (UL)
[0208] 10 parts by weight of the active compounds are dissolved in
90 parts by weight of an organic solvent, for example xylene. This
gives a product to be applied undiluted having an active compound
content of 10% by weight.
[0209] For seed treatment, use is usually made of water-soluble
concentrates (LS), suspensions (FS), dustable powders (DS),
water-dispersible and water-soluble powders (WS, SS), emulsions
(ES), emulsifiable concentrates (EC) and gel formulations (GF).
These formulations can be applied to the seed in undiluted form or,
preferably, diluted. Application can be carried out prior to
sowing.
[0210] In a preferred embodiment a FS formulation is used for seed
treatment. Typcially, a FS formulation may comprise 1-800 g/l of
active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing
agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to
1 liter of a solvent, preferably water.
[0211] The active compounds can be used as such, in the form of
their formulations or the use forms prepared therefrom, for example
in the form of directly sprayable solutions, powders, suspensions
or dispersions, emulsions, oil dispersions, pastes, dustable
products, materials for spreading, or granules, by means of
spraying, atomizing, dusting, spreading or pouring. The use forms
depend entirely on the intended purposes; the intention is to
ensure in each case the finest possible distribution of the active
compounds according to the invention.
[0212] Aqueous use forms can be prepared from emulsion
concentrates, pastes or wettable powders (sprayable powders, oil
dispersions) by adding water. To prepare emulsions, pastes or oil
dispersions, the substances, as such or dissolved in an oil or
solvent, can be homogenized in water by means of a wetter,
tackifier, dispersant or emulsifier. Alternatively, it is possible
to prepare concentrates composed of active substance, wetter,
tackifier, dispersant or emulsifier and, if appropriate, solvent or
oil, and such concentrates are suitable for dilution with
water.
[0213] The active compound concentrations in the ready-to-use
preparations can be varied within relatively wide ranges. In
general, they are from 0.0001 to 10%, preferably from 0.01 to
1%.
[0214] The active compounds may also be used successfully in the
ultra-low-volume process (ULV), by which it is possible to apply
formulations comprising over 95% by weight of active compound, or
even to apply the active compound without additives.
[0215] Various types of oils, wetters, adjuvants, herbicides,
fungicides, other pesticides, or bactericides may be added to the
active compounds, if appropriate not until immediately prior to use
(tank mix). These agents can be admixed with the agents according
to the invention in a weight ratio of 1:100 to 100:1, preferably
1:10 to 10:1.
[0216] Compositions of this invention may also contain other active
ingredients, for example other pesticides, herbicides, fertilizers
such as ammonium nitrate, urea, potash, and superphosphate,
phytotoxicants and plant growth regulators and safeners. These
additional ingredients may be used sequentially or in combination
with the above-described compositions, if appropriate also added
only immediately prior to use (tank mix). For example, the plant(s)
may be sprayed with a composition of this invention either before
or after being treated with other active ingredients.
[0217] The mixtures of a compound I and compounds II and III or the
simultaneous, that is joint or separate, use of a compound I and
compounds II and III are distinguished by being highly active
against a wide range of phytopathogenic fungi, in particular from
the classes of the Ascomycetes, Deuteromycetes, Peronosporomycetes
and Basidiomycetes. Some of them act systemically and can be used
in crop protection as foliar fungicides, as fungicides for seed
dressing and as soil-acting fungicides.
[0218] They are particularly important for controlling a multitude
of fungi on various cultivated plants, such as bananas, cotton,
vegetable species (for example cucumbers, beans and cucurbits),
barley, grass, oats, coffee, potatoes, corn, fruit species, rice,
rye, soya, tomatoes, grapevines, wheat, ornamental plants, sugar
cane and also on a large number of seeds.
[0219] The compounds I and the compounds II and III can be applied
simultaneously, that is jointly or separately, or in succession,
the sequence, in the case of separate application, generally not
having any effect on the result of the control measures.
[0220] They are particularly important in the control of a
multitude of fungi on various cultivated plants, such as wheat,
rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans,
coffee, sugar cane, vines, fruits and ornamental plants, and
vegetables, such as cucumbers, beans, tomatoes, potatoes and
cucurbits, and on the seeds of these plants. They can also be used
in crops which are tolerant to insect or fungal attack because of
breeding, including genetic engineering methods. Moreover, they are
suitable for controlling Botryosphaeria species, Cylindrocarpon
species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum
which infest inter alia the wood or the roots of grapevines.
[0221] They are especially suitable for controlling each of the
following plant diseases: Alternaria species on vegetables,
rapeseed, sugar beet, fruit, rice, soybeans and on potatoes (for
example A. solani or A. alternata) and tomatoes (for example A.
solani or A. alternata) and Alternaria ssp. (black head mold) on
wheat,
Aphanomyces species on sugar beet and vegetables, Ascochyta species
on cereals and vegetables, for example Ascochyta tritici (leaf
spot) on wheat, Bipolaris and Drechslera species on corn (for
example, D. maydis), cereals, rice and lawn, Blumeria graminis
(powdery mildew) on cereals (for example wheat or barley), Botrytis
cinerea (gray mold) on strawberries, vegetables, flowers,
grapevines and wheat (head mold), Bremia lactucae on lettuce,
Cercospora species on corn, rice, sugar beet, and e.g. Cercospora
sojina (leaf spot) or Cercospora kikuchii (leaf spot) on soybeans,
Cladosporium herbarum (ear rot) on wheat, Cochliobolus species on
corn, cereals (e.g. Cochliobolus sativus) and rice (e.g.
Cochliobolus miyabeanus), Colletotricum species on cotton and e.g.
Colletotrichum truncatum (anthracnose) on soybeans, Corynespora
cassiicola (leaf spot) on soybeans, Dematophora necatrix (root/stem
rot) on soybeans, Diaporthe phaseolorum (stem disease) on soybeans,
Drechslera species, Pyrenophora species on corn, cereals, rice and
lawn, on barley (for example, D. teres) or on wheat (for example D.
tritici-repentis), Esca on grapevines, caused by Phaeoacremonium
chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn.
Phellinus punctatus), Elsinoe empelina on grapevines, Epicoccum
spp. (black head mold) on wheat, Exserohilum species on corn,
Erysiphe cichoracearum and Sphaerotheca fuliginea on cucumbers,
Fusarium and Verticillium species on various plants: for example,
F. graminearum or F. culmorum (root rot) on cereals (for example
wheat or barley) or for example F. oxysporum on tomatoes, and
Fusarium solani (stem disease) on soybeans, Gaeumanomyces graminis
(root black) on cereals (for example wheat or barley), Gibberella
species on cereals and rice (for example Gibberella fujikuroi),
Glomerella cingulata on grapevines and other plants, Grainstaining
complex on rice, Guignardia budwelli on grapevines,
Helminthosporium species on corn and rice, Isariopsis clavispora on
grapevines, Macrophomina phaseolina (root/stem rot) on soybeans,
Michrodochium nivale (snow mold) on cereals (for example wheat or
barley), Microsphaera difusa (powdery mildew) on soybeans,
Mycosphaerella species on cereals, bananas and peanuts, such as,
for example, M. graminicola on wheat or M. fijiensis on bananas,
Peronospora species on cabbage (for example P. brassicae), onions,
(for example, P. destructor) and for example Peronospora manshurica
(downy mildew) on soybeans, Phakopsara pachyrhizi (soybean rust)
and Phakopsara meibomiae (soybean rust) on soybeans, Phialophora
gregata (stem disease) on soybeans, Phomopsis species on
sunflowers, grapevines (for example P. viticola) and soybeans (for
example Phomopsis phaseoli), Phytophthora species on various
plants, for example P. capsici on bell pepper, Phytopthora
megasperma (leaf/stem rot) on soybeans, Phytophthora infestans on
potatoes and tomatoes, Plasmopara viticola on grapevines,
Podosphaera leucotricha on apples, Pseudocercosporella
herpotrichoides (eyespot) on cereals (wheat or barley),
Pseudoperonospora on various plants, for example P. cubensis on
cucumber or P. humili on hops, Pseudopezicula tracheiphilai on
grapevines, Puccinia species on various plants, for example P.
triticina, P. striformins, P. hordei or P. graminis on cereals (for
example wheat or barley) or on asparagus (for example P. asparagi),
Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S.
attenuatum, Pyrenophora tritici-repentis (leaf spot) on wheat or
Pyrenophora teres (net spot) on barley, Entyloma oryzae on rice,
Pyricularia grisea on lawn and cereals, Pythium spp. on lawn, rice,
corn, wheat, cotton, oilseed rape, sunflowers, sugar beet,
vegetables and other plants (for example P. ultiumum or P.
aphanidermatum), Ramularia collo-cygni (Ramularia/sunburn
complex/physiological leaf spots) on barley, Rhizoctonia species on
cotton, rice, potatoes, lawn, corn, oilseed rape, potatoes, sugar
beet, vegetables and on various other plants, for example
Rhizoctonia solani (root/stem rot) on soybeans or Rhizoctonia
cerealis (sharp eyespot) on wheat or barley, Rhynchosporium secalis
on barley (leaf spot), rye and triticale, Sclerotinia species on
oilseed rape, sunflowers and, for example Sclerotinia sclerotiorum
(stem disease) or Sclerotinia rolfsii (stem disease) on soybeans,
Septoria glycines (leaf spot) on soybeans, Septoria tritici (leaf
septoria) and Stagonospora nodorum on wheat, Erysiphe (syn.
Uncinula) necator on grapevines, Setospaeria species on corn and
lawn, Sphacelotheca reilinia on corn, Stagonospora nodorum (ear
septoria) on wheat, Thievaliopsis species on soybeans and cotton,
Tilletia species on cereals, Typhula incarnata (snow rot) on wheat
or barley, Ustilago species on cereals, corn (for example U.
maydis) and sugar cane, Venturia species (scab) on apples (for
example V. inaequalis) and pears.
[0222] The target crops may be crops of conventional plants or
crops of genetically modified plants ("GM plants" or "GMOs").
[0223] The compositions according to the invention are therefore
also suitable for use in herbicide-resistant, pest-resistant and/or
fungus-resistant transgenic crops of useful plants, especially
cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops
(e.g. citrus fruits, coffee, bananas), rape, maize and rice.
[0224] Herbicide-resistant crops are to be understood as including
those that have been made tolerant to herbicides or classes of
herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by
means of conventional breeding or genetic engineering methods. An
example of a crop that has been made tolerant by conventional
breeding methods to, for example, imidazolinones such as imazamox
is Clearfield.RTM. summer rape (canola). Examples of crops made
tolerant to herbicides by genetic engineering methods are maize
varieties resistant to, for example, glyphosate or glufosinate,
which are commercially available under the trade names
RoundupReady.RTM. and LibertyLink.RTM., respectively.
[0225] In the context of the present invention, pest-resistant
and/or fungus-resistant transgenic useful plants are expressly
understood to include those useful plants which, in addition to
having the pest resistance and/or fungus resistance, also have
herbicide tolerance. Among the group of herbicide-tolerant useful
plants preference is given, in accordance with the invention, to
useful plants having tolerance with respect to glyphosate,
glufosinate-ammonium, ALS (acetolactate synthase) inhibitors, such
as sulfonylureas, e.g. primisulfuron, prosulfuron and
trifloxysulfuron, or bromoxynil, such as, for example, Bt11 maize
or Herculex I.RTM. maize.
[0226] Pest-resistant transgenic crop plants are to be understood
in the context of the present invention as being plants which have
been so transformed by the use of recombinant DNA techniques that
they are capable of synthesising one or more selectively acting
toxins, such as are known, for example, from toxin-producing
bacteria, especially those of the genus Bacillus.
[0227] Toxins that can be expressed by such transgenic plants
include, for example, insecticidal proteins, e.g. insecticidal
proteins from Bacillus cereus or Bacillus popliae; or insecticidal
proteins from Bacillus thuringiensis, such as alpha-endotoxins,
e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIIA,
CryIIIIB(bi) or Cry9c, or vegetative insecticidal proteins (VIP),
e.g. VIP1, VIP2, VIP3 or VIP3A; or insecticidal proteins of
bacteria that colonise nematodes, for example Photorhabdus spp. or
Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus
nematophilus; toxins produced by animals, such as scorpion toxins,
arachnid toxins, wasp toxins and other insect-specific neurotoxins;
toxins produced by fungi, such as Streptomycetes toxins; plant
lectins, such as pea lectins, barley lectins or snowdrop lectins;
agglutinins; proteinase inhibitors, such as trypsin inhibitors,
serine protease inhibitors, patatin, cystatin, papain inhibitors;
ribosome-inactivating proteins (RIP), such as ricin, maize-RIP,
abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such
as 3-hydroxysteroid-oxidase, ecdysteroid-UDP-glycosyl-transferase,
cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion
channel blockers, such as blockers of sodium or calcium channels,
juvenile hormone esterase, diuretic hormone receptors, stilbene
synthase, bibenzyl synthase, chitinases and glucanases.
[0228] In the context of the present invention there are to be
understood by d-endotoxins, for example CryIA(b), CryIA(c), CryIF,
CryIF(a2), CryIIA(b), CryIIIIA, CryIIIIB(bi) or Cry9c, or
vegetative insecticidal proteins (VIP), for example VIP1, VIP2,
VIP3 or VIP3A, expressly also hybrid toxins, truncated toxins and
modified toxins. Hybrid toxins are produced recombinantly by a new
combination of different domains of those proteins (see, for
example, WO 02/15701). An example of a truncated toxin is a
truncated CryIA(b), which is expressed in Bt11 maize of Syngenta
Seeds SAS, as described hereinbelow. In the case of modified
toxins, one or more amino acids of the naturally occurring toxin
is/are replaced. In such amino acid replacements, preferably
non-naturally present protease recognition sequences are inserted
into the toxin, such as, for example, in the case of CryIIIA055, a
cathepsin-D-recognition sequence is inserted into a CryIIIA toxin
(see WO 03/018810).
[0229] Examples of such toxins or transgenic plants capable of
synthesising such toxins are disclosed, for example, in EP-A 374
753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878 and WO
03/052073.
[0230] The processes for the production of such transgenic plants
are generally known to the person skilled in the art and are
described, for example, in the publications mentioned above.
CryI-type deoxyribonucleic acids and their preparation are known,
for example, from WO 95/34656, EP-A 367 474, EP-A 401 979 and WO
90/13651.
[0231] The toxin contained in the transgenic plants provides the
plants with tolerance to harmful insects. Such insects can occur in
any taxonomic group of insects, but are especially commonly found
in beetles (Coleoptera), two-winged insects (Diptera) and
butterflies (Lepidoptera).
[0232] The following harmful insects from different taxonomic
groups are especially common in maize crops:
Ostrinia nubilalis, European corn borer, Agrotis ipsilon, black
cutworm, Helicoverpa zea, corn earworm, Spodoptera frugiperda, fall
armyworm, Diatraea grandiosella, southwestern corn borer,
Elasmopalpus lignosellus, lesser cornstalk borer, Diatraea
saccharalis, sugarcane borer, Diabrotica virgifera virgifera,
western corn rootworm, Diabrotica longicornis barberi, northern
corn rootworm, Diabrotica undecimpunctata howardi, southern corn
rootworm, Melanotus spp., wireworms, Cyclocephala borealis,
northern masked chafer (white grub), Cyclocephala immaculata,
southern masked chafer (white grub), Popillia japonica, Japanese
beetle, Chaetocnema pulicaria, corn flea beetle, Sphenophorus
maidis, maize billbug, Rhopalosiphum maidis, corn leaf aphid,
Anuraphis maidiradicis, corn root aphid, Blissus leucopterus
leucopterus, chinch bug, Melanoplus femurrubrum, red-legged
grasshopper, Melanoplus sanguinipes, migratory grasshopper, Hylemya
platura, seedcom maggot, Agromyza parvicornis, corn blotch
leafminer, Anaphothrips obscurus, grass thrips, Solenopsis milesta,
thief ant, Tetranychus urticae, two-spotted spider mite.
[0233] Transgenic plants containing one or more genes that code for
an insecticidal resistance and express one or more toxins are known
and some of them are commercially available. Examples of such
plants are: YieldGard.RTM. (maize variety that expresses a CryIA(b)
toxin); YieldGard Rootworm.RTM. (maize variety that expresses a
CryIIIIB(bi) toxin); YieldGard Plus.RTM. (maize variety that
expresses a CryIA(b) and a CryIIIIB(bi) toxin); Starlink.RTM.
(maize variety that expresses a Cry9(c) toxin); Herculex I.RTM.
(maize variety that expresses a CryIF(a2) toxin and the enzyme
phosphinothricin N-acetyl-transferase (PAT) to achieve tolerance to
the herbicide glufosinate ammonium); NuCOTN 33B.RTM. (cotton
variety that expresses a CryIA(c) toxin); Boligard I.RTM. (cotton
variety that expresses a CryIA(c) toxin); Boligard 10 (cotton
variety that expresses a CryIA(c) and a CryIIA(b) toxin);
VIPCOT.RTM. (cotton variety that expresses a VIP toxin);
NewLeaf.RTM. (potato variety that expresses a CryIIIIA toxin);
NatureGard.RTM. and Protecta.RTM..
[0234] Further examples of such transgenic crops are:
1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31
790 St. Sauveur, France, registration number C/FR/96/05/10.
Genetically modified Zea mays which has been rendered resistant to
attack by the European corn borer (Ostrinia nubilalis and Sesamia
nonagrioides) by transgenic expression of a truncated CryIA(b)
toxin. Bt11 maize also transgenically expresses the enzyme PAT to
achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176
Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.
Sauveur, France, registration number C/FR/96/05/10. Genetically
modified Zea mays which has been rendered resistant to attack by
the European corn borer (Ostrinia nuhilalis and Sesamia
nonagrioides) by transgenic expression of a CryIA(b) toxin. Bt176
maize also transgenically expresses the enzyme PAT to achieve
tolerance to the herbicide glufosinate ammonium. 3. MIR604 Maize
from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.
Sauveur, France, registration number C/FR/96/05/10. Maize which has
been rendered insect-resistant by transgenic expression of a
modified CryIHA toxin. This toxin is Cry3A055 modified by insertion
of a cathepsin-D-protease recognition sequence. The preparation of
such transgenic maize plants is described in WO 03/018810. 4. MON
863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,
B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863
expresses a CryIIIIB(bi)toxin and has resistance to certain
Coleoptera insects. 5. IPC 531 Cotton from Monsanto Europe S.A.
270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration
number C/ES/96/02. 6. 1507 Maize from Pioneer Overseas Corporation,
Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/N
LJ00/10. Genetically modified maize for the expression of the
protein CryI F for achieving resistance to certain Lepidoptera
insects and of the PAT protein for achieving tolerance to the
herbicide glufosinate ammonium. 7. NK603.times.MON 810 Maize from
Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels,
Belgium, registration number C/GB/02/M3/03. Consists of
conventionally bred hybrid maize varieties by crossing the
genetically modified varieties NK603 and MON 810. NK603.times.MON
810 Maize transgenically expresses the protein CP4 EPSPS, obtained
from Agrobacterium sp. strain CP4, which imparts tolerance to the
herbicide Roundup.RTM. (contains glyphosate), and also a CryIA(b)
toxin obtained from Bacillus thuringiensis subsp. kurstaki which
brings about tolerance to certain Lepidoptera, including the
European corn borer.
[0235] Transgenic crops of insect-resistant plants are also
described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit,
Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report
2003, (http://bats.ch).
[0236] In the context of the present invention, fungus-resistant
transgenic crop plants are to be understood as being those which
have been so transformed by the use of recombinant DNA techniques
that they are capable of synthesising antipathogenic substances
having a selective action, such as, for example, the so-called
"pathogenesis-related proteins" (PRPs, see e.g. EP-A 392 225).
Examples of such antipathogenic substances and transgenic plants
capable of synthesising such antipathogenic substances are known,
for example, from EP-A 392 225, WO 95/33818 and EP-A 353 191. The
methods of producing such transgenic plants are generally known to
the person skilled in the art and are described, for example, in
the publications mentioned above.
[0237] Antipathogenic substances which can be expressed by such
transgenic plants include, for example, ion channel blockers, such
as blockers for sodium and calcium channels, for example the viral
KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases;
chitinases; glucanases; the so-called "pathogenesis-related
proteins" (PRPs; see e.g. EP-A 392 225); antipathogenic substances
produced by microorganisms, for example peptide antibiotics or
heterocyclic antibiotics (see e.g. WO 95/33818) or protein or
polypeptide factors involved in plant pathogen defence (so-called
"plant disease resistance genes", as described in WO 03/000906).
Further areas of use of the compositions according to the invention
are the protection of stored goods and storerooms and the
protection of raw materials, such as wood, textiles, floor
coverings or buildings, and also in the hygiene sector, especially
the protection of humans, domestic animals and productive livestock
against pests of the mentioned type.
[0238] In the context of the invention transgenic plants may
contain one or more genes that code for an insecticidal resistance
as well as for a herbicidal resistance, as described above (e.g. RR
Bollguard.RTM. or RR Yieldguard.RTM. traits). Those are considered
transgenic plants containing a double or even triple stacked genes.
Furthermore, this concept of multiple stacking of genes or events
in a transgenic plant can be considered also for a broader and
larger application, such as fungicidal resistance or drought
resistance. The latter are to be understood of which have been so
transformed by the use of recombinant DNA techniques that they are
capable providing stress resistance under drought selection
pressure to the crop plant. Furthermore, genes which increase the
yield potential of a given crop plant per se, when introduced by
transformation technologies with the use of recombinant DNA,
providing additional yield by modifying a given physiological
pathway of the crop plant, have to be considered in the multiple
stacking concept of transgenic crop plants, e.g. RR2yield.RTM. in
soybean.
[0239] The mixtures of the compounds I and active compounds II and
III are furthermore suitable for controlling harmful fungi in the
protection of materials (for example wood, paper, paint
dispersions, fibers or fabrics) and in the protection of stored
products. In the protection of wood, particular attention is paid
to the following harmful fungi: Ascomycetes, such as Ophiostoma
spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp.,
Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.;
Basidiomycetes, such as Coniophora spp., Coriolus spp.,
Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp.,
Serpula spp. and Tyromyces spp., Deuteromycetes, such as
Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma
spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as
Mucor spp., additionally in the protection of materials the
following yeasts: Candida spp. and Saccharomyces cerevisae.
[0240] The compound I and the compound II are usually applied in a
weight ratio of from 5000:1 to 1:5000, preferabley500:1 to 1:100,
more preferably from 100:1 to 1:100, in particular from 20:1 to
1:20, most preferred from 10:1 to 1:10.
[0241] The compound III is added in a weight ratio of from 20:1 to
1:20 to the compound I.
[0242] Alternatively the compound III is added in a weight ratio of
from 20:1 to 1:20 to the compound II.
[0243] When preparing the mixtures, it is preferred to employ the
pure active compounds I, II and III, to which further active
compounds against harmful fungi or against other pests, such as
insects, arachnids or nematodes, or else herbicidal or
growth-regulating active compounds or fertilizers can be added as
further active components according to need.
[0244] Usually, mixtures of a compound I with two or, if
appropriate, more active components may be advantageous.
[0245] Suitable further active components in the above sense are in
particular the active compounds II and III, mentioned at the outset
and in particular the preferred active compounds mentioned
above.
[0246] The mixtures of the compounds I and active compounds II and
III are employed by treating the fungi or the plants, seeds,
materials or soil to be protected from fungal attack with a
fungicidally effective amount of the active compounds. The
application can be carried out both before and after the infection
of the materials, plants or seeds by the fungi.
[0247] In the method of combating harmful fungi depending on the
type of compound and the desired effect, the application rates of
the mixtures according to the invention are from 5 g/ha to 2000
g/ha, preferably from 50 to 900 g/ha, in particular from 50 to 750
g/ha.
[0248] Correspondingly, the application rates for the compound I
are generally from 1 to 1000 g/ha, preferably from 10 to 900 g/ha,
in particular from 20 to 750 g/ha.
[0249] Correspondingly, the application rates for the active
compounds II and III, resp., are generally from 1 to 2000 g/ha,
preferably from 10 to 900 g/ha, in particular from 40 to 500
g/ha.
[0250] The method for controlling harmful fungi is carried out by
the separate or joint application of a compound I and the active
compounds II and III or the mixtures of the compound I and the
active compounds II and III by spraying or dusting the seeds, the
plants or the soil before or after sowing of the plants or before
or after emergence of the plants.
[0251] The treatment can be made into the seedbox before planting
into the field.
[0252] The compounds I, II and III or the mixtures or the
corresponding formulations are applied by treating the harmful
fungi, the plants, seeds, soils, areas, materials or spaces to be
kept free from them with a fungicidally effective amount of the
mixture or, in the case of separate application, of the compounds
I, II and III. Application can be carried out before or after
infection by the harmful fungi.
[0253] The mixtures of compounds I, II and II, or the compounds I,
II and III used simultaneously, that is jointly or separately,
exhibit also outstanding action against pests from the following
orders:
insects from the order of the lepidopterans (Lepidoptera), for
example Agrotis ypsilon, Agrotis segetum, Alabama argillacea,
Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma,
Bupalus piniarius, Cacoecia murinana, Capua reticulana, Chematobia
brumata, Choristoneura fumiferana, Choristoneura occidentalis,
Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania
nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus
lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia
subterranea, Galleria mellonella, Grapholitha funebrana,
Grapholitha molesta, Heliothis armigera, Heliothis virescens,
Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria
cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina
fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera
scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege
sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia
clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia
pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora
gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea
operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena
scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia
frustrana, Scrobipalpula absoluta, Sitotroga cerealella,
Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera
littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix
viridana, Trichoplusia ni and Zeiraphera canadensis, beetles
(Coleoptera), for example Agrilus sinuatus, Agriotes lineatus,
Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar,
Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous
haemorrhoidalis, Atomaria linearis, Blastophagus piniperda,
Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus
lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata,
Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi,
Chaetocnema tibialis, Conoderus vespertinus, Criceris asparagi,
Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata,
Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera,
Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus
brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera
postica, Ips typographus, Lema bilineata, Lema melanopus,
Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus
oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha
hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus
sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius
pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha
horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia
japonica, Sitona lineatus and Sitophilus granaria, flies,
mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes
vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles
crucians, Anopheles albimanus, Anopheles gambiae, Anopheles
freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles
quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya
bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops
discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia
hominivorax, Contarinia sorghicola Cordylobia anthropophaga,
Culicoides furens, Culex pipiens, Culex nigripalpus, Culex
quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta
melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia
antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia
hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus
intestinalis, Glossina morsitans, Glossina palpalis, Glossina
fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis
equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata,
Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia
caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis,
Mansonia titillanus, Mayetiola destructor, Musca domestica, Muscina
stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya
hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,
Phlebotomus argentipes, Psorophora columbiae, Psila rosae,
Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi,
Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga sp.,
Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus
atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and
Tipula paludosa thrips (Thysanoptera), e.g. Dichromothrips
corbetti, Dichromothrips ssp, Frankliniella fusca, Frankliniella
occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips
oryzae, Thrips palmi and Thrips tabaci, termites (Isoptera), e.g.
Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus,
Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes
lucifugus, Termes natalensis, and Coptotermes formosanus,
cockroaches (Blattaria-Blattodea), e.g. Blattella germanica,
Blattella asahinae, Periplaneta americana, Periplaneta japonica,
Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta
australasiae, and Blatta orientalis, true bugs (Hemiptera), e.g.
Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus,
Dysdercus cingulatus, Dysdercus intermedius, Eurygaster
integriceps, Euschistus impictiventris, Leptoglossus phyllopus,
Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma
quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon
onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis
forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis
schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum,
Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui,
Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus
prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha
gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia
nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum
pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae,
Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae,
Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae,
Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus
ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri,
Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,
Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus
ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi,
Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis
graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes
vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex
lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and
Arilus critatus. ants, bees, wasps, sawflies (Hymenoptera), e.g.
Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes,
Atta laevigata, Atta robusta, Atta sexdens, Atta texana,
Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea,
Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta,
Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus,
Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla
occidentalis, Bombus spp. Vespula squamosa, Paravespula vulgaris,
Paravespula pennsylvanica, Paravespula germanica, Dolichovespula
maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus,
and Linepithema humile, crickets, grasshoppers, locusts
(Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa,
Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum,
Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus,
Nomadacris septemfasciata, Schistocerca americana, Schistocerca
gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus
senegalensis, Zonozerus variegatus, Hieroglyphus daganensis,
Kraussaria angulifera, Calliptamus italicus, Chortoicetes
terminifera, and Locustana pardalina, Arachnoidea, such as
arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and
Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum,
Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus
decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor
andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes
ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus,
Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi,
Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini,
Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus,
Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes
scabiei, and Eriophyidae spp. such as Aculus schlechtendali,
Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp.
such as Phytonemus pallidus and Polyphagotarsonemus latus;
Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae
spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai,
Tetranychus pacificus, Tetranychus telarius and Tetranychus
urticae, Panonychus ulmi, Panonychus citri, and Oligonychus
pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles
reclusa, fleas (Siphonaptera), e.g. Ctenocephalides felis,
Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga
penetrans, and Nosopsyllus fasciatus, silverfish, firebrat
(Thysanura), e.g. Lepisma saccharina and Thermobia domestica,
centipedes (Chilopoda), e.g. Scutigera coleoptrata, millipedes
(Diplopoda), e.g. Narceus spp., Earwigs (Dermaptera), e.g.
forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus
capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus
eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis,
Menopon gallinae, Menacanthus stramineus and Solenopotes
capillatus, plant parasitic nematodes such as root-knot nematodes,
Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne exigua,
Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and
other Meloidogyne species; cyst nematodes, Globodera rostochiensis,
Globodera pallida, Globodera tabacum and other Globodera species,
Heterodera avenae, Heterodera glycines, Heterodera schachtii,
Heterodera trifolii, and other Heterodera species; seed gall
nematodes, Anguina funesta, Anguina tritici and other Anguina
species; stem and foliar nematodes, Aphelenchoides besseyi,
Aphelenchoides fragariae, Aphelenchoides ritzemabosi and other
Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus
and other Belonolaimus species; pine nematodes, Bursaphelenchus
xylophilus and other Bursaphelenchus species; ring nematodes,
Criconema species, Criconemella species, Criconemoides species, and
Mesocriconema species; stem and bulb nematodes, Ditylenchus
destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and
other Ditylenchus species; awl nematodes, Dolichodorus species;
spiral nematodes, Helicotylenchus dihystera, Helicotylenchus
multicinctus and other Helicotylenchus species, Rotylenchus
robustus and other Rotylenchus species; sheath nematodes,
Hemicycliophora species and Hemicriconemoides species;
Hirshmanniella species; lance nematodes, Hoplolaimus columbus,
Hoplolaimus galeatus and other Hoplolaimus species; false root-knot
nematodes, Nacobbus aberrans and other Nacobbus species; needle
nematodes, Longidorus elongates and other Longidorus species; pin
nematodes, Paratylenchus species; lesion nematodes, Pratylenchus
brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus,
Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus
penetrans, Pratylenchus scribneri, Pratylenchus vulnus,
Pratylenchus zeae and other Pratylenchus species; Radinaphelenchus
cocophilus and other Radinaphelenchus species; burrowing nematodes,
Radopholus similis and other Radopholus species; reniform
nematodes, Rotylenchulus reniformis and other Rotylenchulus
species; Scutellonema species; stubby root nematodes, Trichodorus
primitivus and other Trichodorus species; Paratrichodorus minor and
other Paratrichodorus species; stunt nematodes, Tylenchorhynchus
claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus
species and Merlinius species; citrus nematodes, Tylenchulus
semipenetrans and other Tylenchulus species; dagger nematodes,
Xiphinema americanum, Xiphinema index, Xiphinema diversicaudatum
and other Xiphinema species; and other plant parasitic nematode
species.
[0254] Moreover, the inventive mixtures are especially useful for
the control of Lepidoptera, Coleoptera, Diptera, Thysanoptera and
Hymenoptera.
[0255] Moreover, the inventive mixtures are especially useful for
the control of non-crop pests (household, turf, ornamental).
[0256] The mixtures according to the invention can be applied to
any and all developmental stages of pests, such as egg, larva,
pupa, and adult. The pests may be controlled by contacting the
target pest, its food supply, habitat, breeding ground or its locus
with a pesticidally effective amount of the inventive mixtures or
of compositions comprising the mixtures.
[0257] "Locus" means a plant, seed, soil, area, material or
environment in which a pest is growing or may grow.
[0258] In general, "pesticidally effective amount" means the amount
of the inventive mixtures or of compositions comprising the
mixtures needed to achieve an observable effect on growth,
including the effects of necrosis, death, retardation, prevention,
and removal, destruction, or otherwise diminishing the occurrence
and activity of the target organism.
[0259] The pesticidally effective amount can vary for the various
mixtures/compositions used in the invention. A pesticidally
effective amount of the mixtures/compositions will also vary
according to the prevailing conditions such as desired pesticidal
effect and duration, weather, target species, locus, mode of
application, and the like.
[0260] The inventive mixtures or compositions of these mixtures can
also be employed for protecting plants from attack or infestation
by insects, acarids or nematodes comprising contacting a plant, or
soil or water in which the plant is growing.
[0261] In the context of the present invention, the term plant
refers to an entire plant, a part of the plant or the propagation
material of the plant, that is, the seed or the seedling.
[0262] Plants which can be treated with the inventive mixtures
include all genetically modified plants or transgenic plants, e.g.
crops which tolerate the action of herbicides or fungicides or
insecticides owing to breeding, including genetic engineering
methods, or plants which have modified characteristics in
comparison with existing plants, which can be generated for example
by traditional breeding methods and/or the generation of mutants,
or by recombinant procedures.
[0263] Some of the inventive mixtures have systemic action and can
therefore be used for the protection of the plant shoot against
foliar pests as well as for the treatment of the seed and roots
against soil pests. The term seed treatment comprises all suitable
seed treatment techniques known in the art, such as seed dressing,
seed coating, seed dusting, seed soaking and seed pelleting.
[0264] The compounds I and the compounds II and II, resp. can be
applied simultaneously, that is jointly or separately, or in
succession, the sequence, in the case of separate application,
generally not having any effect on the result of the control
measures.
[0265] The inventive mixtures are also suitable for the protection
of the seed and the seedlings' roots and shoots, preferably the
seeds, against soil pests.
[0266] Compositions, which are especially useful for seed treatment
are e.g.:
A Soluble concentrates (SL, LS)
D Emulsions (EW, EO, ES)
E Suspensions (SC, OD, FS)
[0267] F Water-dispersible granules and water-soluble granules (WG,
SG) G Water-dispersible powders and water-soluble powders (WP, SP,
WS)
H Gel-Formulations (GF)
[0268] I Dustable powders (DP, DS)
[0269] Conventional seed treatment formulations include for example
flowable concentrates FS, solutions LS, powders for dry treatment
DS, water dispersible powders for slurry treatment WS,
water-soluble powders SS and emulsion ES and EC and gel formulation
GF. These formulations can be applied to the seed diluted or
undiluted. Application to the seeds is carried out before sowing,
either directly on the seeds or after having pregerminated the
latter. Preferred are FS formulations.
[0270] In the treatment of seed, the application rates of the
inventive mixture are generally from 0.001 to 10 kg per 100 kg of
seed, dependent from the desired effect and the kind of seed.
Application rates are preferably from 1 to 1000 g/100 kg of seed,
more preferably from 1 to 750 g/100 kg, in particular from 5 to 500
g/100 kg. The separate or joint application of the compounds I and
II or of the mixtures of the compounds I and II is carried out by
spraying or dusting the seeds, the seedlings, the plants or the
soils before or after sowing of the plants or before or after
emergence of the plants.
[0271] The invention also relates to the propagation products of
plants, and especially the seed comprising, that is, coated with
and/or containing, a mixture as defined above or a composition
containing the mixture of two or more active ingredients or a
mixture of two or more compositions each providing one of the
active ingredients. The seed comprises the inventive mixtures in an
amount of from 0.1 g to 10 kg per 100 kg of seed.
[0272] The inventive mixtures are effective through both contact
(via soil, glass, wall, bed net, carpet, plant parts or animal
parts), and ingestion (bait, or plant part) and through
trophallaxis and transfer.
[0273] Preferred application methods are into water bodies, via
soil, cracks and crevices, pastures, manure piles, sewers, into
water, on floor, wall, or by perimeter spray application and
bait.
[0274] According to another preferred embodiment of the invention,
for use against non crop pests such as ants, termites, wasps,
flies, mosquitoes, crickets, locusts, or cockroaches the inventive
mixtures are prepared into a bait preparation.
[0275] The bait can be a liquid, a solid or a semisolid preparation
(e.g. a gel). The bait employed in the composition is a product
which is sufficiently attractive to incite insects such as ants,
termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to
eat it. This attractant may be chosen from feeding stimulants or
para and/or sex pheromones The compound I and the compound II
applied in a weight ratio of from 500:1 to 1:500, preferably from
500:1 to 1:100, more preferably from 100:1 to 1:100, in particular
from 20:1 to 1:20, most preferred from 10:1 to 1:10 readily known
in the art.
[0276] Methods to control infectious diseases transmitted by
insects (e.g. malaria, dengue and yellow fever, lymphatic
filariasis, and leishmaniasis) with the inventive mixtures and
their respective compositions also comprise treating surfaces of
huts and houses, air spraying and impregnation of curtains, tents,
clothing items, bed nets, tsetse-fly trap or the like. Insecticidal
compositions for application to fibers, fabric, knitgoods,
nonwovens, netting material or foils and tarpaulins preferably
comprise a composition including the inventive mixtures, optionally
a repellent and at least one binder.
[0277] The inventive mixtures and the compositions comprising them
can be used for protecting wooden materials such as trees, board
fences, sleepers, etc. and buildings such as houses, outhouses,
factories, but also construction materials, furniture, leathers,
fibers, vinyl articles, electric wires and cables etc. from ants
and/or termites, and for controlling ants and termites from doing
harm to crops or human being (e.g. when the pests invade into
houses and public facilities).
[0278] In the case of soil treatment or of application to the pests
dwelling place or nest, the quantity of active ingredient ranges
from 0.0001 to 500 g per 100 m.sup.2, preferably from 0.001 to 20 g
per 100 m.sup.2.
[0279] Customary application rates in the protection of materials
are, for example, from 0.01 g to 1000 g of active compound per
m.sup.2 treated material, desirably from 0.1 g to 50 g per
m.sup.2.
[0280] Insecticidal compositions for use in the impregnation of
materials typically contain from 0.001 to 95 weight %, preferably
from 0.1 to 45 weight %, and more preferably from 1 to 25 weight %
of at least one repellent and/or insecticide.
[0281] For use in bait compositions, the typical content of active
ingredient is from 0.0001 weight % to 15 weight %, desirably from
0.001 weight % to 5% weight % of active compound. The composition
used may also comprise other additives such as a solvent of the
active material, a flavoring agent, a preserving agent, a dye or a
bitter agent. Its attractiveness may also be enhanced by a special
color, shape or texture.
[0282] For use in spray compositions, the content of the mixture of
the active ingredients is from 0.001 to 80 weights %, preferably
from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight
%.
[0283] For use in treating crop plants, the rate of application of
the mixture of the active ingredients of this invention may be in
the range of 0.1 g to 4000 g per hectare, desirably from 25 g to
600 g per hectare, more desirably from 50 g to 500 g per
hectare.
[0284] It was also an object of the present invention to provide
mixtures suitable for treating, controlling, preventing and
protecting warm-blooded animals, including humans, and fish against
infestation and infection by pests. Problems that may be
encountered with pest control on or in animals and/or humans are
similar to those described at the outset, namely the need for
reduced dosage rates, and/or enhanced spectrum of activity and/or
combination of knock-down activity with prolonged control and/or
resistance management.
[0285] This invention also provides a method for treating,
controlling, preventing and protecting warm-blooded animals,
including humans, and fish against infestation and infection by
pests of the orders Siphonaptera, Hymenoptera, Hemiptera,
Orthoptera, Acarina, Phthiraptera, and Diptera, which comprises
orally, topically or parenterally administering or applying to said
animals a pesticidally effective amount of mixtures according to
the invention.
[0286] The invention also provides a process for the preparation of
a composition for treating, controlling, preventing or protecting a
warm-blooded animal or a fish against infestation or infection by
pests of the Siphonaptera, Hymenoptera, Hemiptera, Orthoptera,
Acarina, Phthiraptera, and Diptera orders which comprises a
pesticidally effective amount of a mixture according to the
invention.
[0287] The above method is particularly useful for controlling and
preventing infestations and infections in warm-blooded animals such
as cattle, sheep, swine, camels, deer, horses, poultry, goats, dogs
and cats as well as humans.
[0288] Infestations in warm-blooded animals and fish including, but
not limited to, lice, biting lice, ticks, nasal bots, keds, biting
flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats,
mosquitoes and fleas may be controlled, prevented or eliminated by
the mixtures according to the invention.
[0289] For oral administration to warm-blooded animals, the
mixtures according to the invention may be formulated as animal
feeds, animal feed premixes, animal feed concentrates, pills,
solutions, pastes, suspensions, drenches, gels, tablets, boluses
and capsules. In addition, the mixtures according to the invention
may be administered to the animals in their drinking water. For
oral administration, the dosage form chosen should provide the
animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day
of the mixture.
[0290] Alternatively, the mixtures according to the invention may
be administered to animals parenterally, for example, by
intraruminal, intramuscular, intravenous or subcutaneous injection.
The mixtures according to the invention may be dispersed or
dissolved in a physiologically acceptable carrier for subcutaneous
injection. Alternatively, the mixtures according to the invention
may be formulated into an implant for subcutaneous administration.
In addition the mixtures according to the invention may be
transdermally administered to animals. For parenteral
administration, the dosage form chosen should provide the animal
with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the
mixture.
[0291] The mixtures according to the invention may also be applied
topically to the animals in the form of dips, dusts, powders,
collars, medallions, sprays, spot-on and pour-on formulations. For
topical application, dips and sprays usually contain 0.5 ppm to
5,000 ppm and preferably 1 ppm to 3000 ppm of the inventive
compounds. In addition, the mixtures according to the invention may
be formulated as ear tags for animals, particularly quadrupeds such
as cattle and sheep.
BIOLOGICAL EXAMPLES
1) Fungicidal Action
[0292] The fungicidal effect of the compound and the mixtures could
be demonstrated by the following tests:
[0293] The active compounds, separately or jointly, were prepared
as a stock solution comprising 0.25% by weight of active compound
in acetone or DMSO. 1% by weight of the emulsifier Uniperol.RTM. EL
(wetting agent having emulsifying and dispersant action based on
ethoxylated alkylphenols) was added to this solution, and the
mixture was diluted with water to the desired concentration.
[0294] The visually determined percentages of infected leaf areas
were converted into efficacies in % of the untreated control:
[0295] The efficacy (E) is calculated as follows using Abbot's
formula:
E=(1-.alpha./.beta.)100
.alpha. corresponds to the fungicidal infection of the treated
plants in % and .beta. corresponds to the fungicidal infection of
the untreated (control) plants in %
[0296] An efficacy of 0 means that the infection level of the
treated plants corresponds to that of the untreated control plants;
an efficacy of 100 means that the treated plants were not
infected.
[0297] The expected efficacies of mixtures of active compounds were
determined using Colby's formula (Colby, S. R. "Calculating
synergistic and antagonistic responses of herbicide Combinations",
Weeds, 15, 20-22, 1967) and compared with the observed
efficacies.
E=x+y-xy/100 Colby's formula [0298] E expected efficacy, expressed
in % of the untreated control, when using the mixture of the active
compounds A and B at the concentrations a and b [0299] x efficacy,
expressed in % of the untreated control, when using the active
compound A at the concentration a [0300] y efficacy, expressed in %
of the untreated control, when using the active compound B at the
concentration b
Use Example 1
Fungicidal Control of Brown Spot caused by Cochliobolus miyabeanus
(Protective)
[0301] Leaves of pot-grown rice seedlings were sprayed to run-off
with an aqueous suspension, containing the concentration of active
ingredient as described below prepared from the stock solution. The
plants were allowed to air-dry. At the following day the plants
were inoculated with an aqueous spore suspension of Cochliobolus
miyabeanus. Then the trial plants were immediately transferred to a
humid chamber. After 6 days at 22-24.degree. C. and a relative
humidity close to 100% the extent of fungal attack on the leaves
was visually assessed as % diseased leaf area.
[0302] The test results show that, by virtue of strong synergism,
the activity of the mixtures according to the invention is
considerably higher than had been predicted using Colby's
formula.
2) Action Against Animal Pests
[0303] The following tests demonstrate the control efficacy of
compounds and mixtures of compounds II and III of this invention on
specific pests. However, the pest control protection afforded by
the compounds, mixtures or compositions is not limited to these
species. The efficacy of ternary mixtures according to the
invention can be determined accordingly. In certain instances,
combinations of a compound of this invention with other
invertebrate pest control compounds or agents are found to exhibit
synergistic effects against certain important invertebrate
pests.
[0304] The analysis of synergism or antagonism between the mixtures
or compositions was determined using Colby's equation.
Use Example 2
[0305] For evaluating control of vetch aphid (Megoura viciae)
through contact or systemic means the test unit consisted of
24-well-microtiter plates containing broad bean leaf disks.
[0306] The compounds or mixtures were formulated using a solution
containing 75% water and 25% DMSO. Different concentrations of
formulated compounds or mixtures were sprayed onto the leaf disks
at 2.5 .mu.l, using a custom built micro atomizer, at two
replications.
[0307] For experimental mixtures in these tests identical volumes
of both mixing partners at the desired concentrations respectively,
were mixed together.
[0308] After application, the leaf disks were air-dried and 5-8
adult aphids placed on the leaf disks inside the microtiter plate
wells. The aphids were then allowed to suck on the treated leaf
disks and incubated at 23.+-.1.degree. C., 50.+-.5% RH for 5 days.
Aphid mortality and fecundity was then visually assessed.
[0309] In this test the compound I-2, and
N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazol-
e-4-carboxamide (compound 2.1) and
5-chloro-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tri-
azolo[1,5-a]pyrimidine (compound 2.2) were used.
[0310] Following results were obtained:
TABLE-US-00003 Vetch Aphid ppm Average Control % I-2 0.5 0 I-2 2.5
0 2.1 1000 0 2.2 40 0 I-2 + 2.1 0.5 + 1000 100* I-2 + 2.2 2.5 + 40
75* *synergistic control effect according to Colby's equation
Use Example 3
[0311] For evaluating control of boll weevil (Anthonomus grandis)
the test unit consisted of 24-well-microtiter plates containing an
insect diet and 20-30 A. grandis eggs.
[0312] The compounds or mixtures were formulated using a solution
containing 75% water and 25% DMSO. Different concentrations of
formulated compounds or mixtures were sprayed onto the insect diet
at 20 .mu.l, using a custom built micro atomizer, at two
replications.
[0313] For experimental mixtures in these tests identical volumes
of both mixing partners at the desired concentrations respectively,
were mixed together.
[0314] After application, microtiter plates were incubated at
23.+-.1.degree. C., 50.+-.5% RH for 5 days. Egg and larval
mortality was then visually assessed.
[0315] In this test the compound I-2, and prochloraz,
pyraclostrobin,
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide (compound 3.1), and
N-(3',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-
-4-carboxamide (compound 3.2), resp., were used.
[0316] Following results were obtained:
TABLE-US-00004 Boll Weevil ppm Average Control % I-2 0.5 0
prochloraz 40 0 pyraclostrobin 40 0 3.1 40 0 3.2 200 0 I-2 +
prochloraz 0.5 + 40 75* I-2 + pyraclostrobin 0.5 + 40 75* I-2 + 3.1
0.5 + 40 100* I-2 + 3.2 0.5 + 200 100* *synergistic control effect
according to Colby's equation
Use Example 4
[0317] For evaluating control of Mediterranean fruitfly (Ceratitis
capitata) the test unit consisted of 96-well-microtiter plates
containing an insect diet and 50-80 C. capitata eggs.
[0318] The compounds or mixtures were formulated using a solution
containing 75% water and 25% DMSO. Different concentrations of
formulated compounds or mixtures were sprayed onto the insect diet
at 5 .mu.l, using a custom built micro atomizer, at two
replications.
[0319] For experimental mixtures in these tests identical volumes
of both mixing partners at the desired concentrations respectively,
were mixed together.
[0320] After application, microtiter plates were incubated at
28.+-.1.degree. C., 80.+-.5% RH for 5 days. Egg and larval
mortality was then visually assessed.
Use Example 5
[0321] For evaluating control of tobacco budworm (Heliothis
virescens) the test unit consisted of 96-well-microtiter plates
containing an insect diet and 15-25H. virescens eggs.
[0322] The compounds or mixtures were formulated using a solution
containing 75% water and 25% DMSO. Different concentrations of
formulated compounds or mixtures were sprayed onto the insect diet
at 10 .mu.l, using a custom built micro atomizer, at two
replications.
[0323] For experimental mixtures in these tests identical volumes
of both mixing partners at the desired concentrations respectively,
were mixed together.
[0324] After application, microtiter plates were incubated at
28.+-.1.degree. C., 80.+-.5% RH for 5 days. Egg and larval
mortality was then visually assessed.
[0325] In this test the compound I-2, and prochloraz, and
pyraclostrobin, resp., were used.
[0326] Following results were obtained:
TABLE-US-00005 Tobacco budworm ppm Average Control % I-2 0.5 0 I-2
2.5 37.5 prochloraz 8 0 pyraclostrobin 200 0 I-2 + prochloraz 2.5 +
8 87.5* I-2 + pyraclostrobin 0.5 + 200 50* *synergistic control
effect according to Colby's equation
Use Example 6
[0327] For evaluating control of green peach aphid (Myzus persicae)
through systemic means the test unit consisted of
96-well-microtiter plates containing liquid artificial diet under
an artificial membrane.
[0328] The compounds or mixtures were formulated using a solution
containing 75% water and 25% DMSO. Different concentrations of
formulated compounds or mixtures were pipetted into the aphid diet,
using a custom built pipetter, at two replications.
[0329] For experimental mixtures in these tests identical volumes
of both mixing partners at the desired concentrations respectively,
were mixed together.
[0330] After application, 5-8 adult aphids were placed on the
artificial membrane inside the microtiter plate wells. The aphids
were then allowed to suck on the treated aphid diet and incubated
at 23.+-.1.degree. C., 50.+-.5% RH for 3 days. Aphid mortality and
fecundity was then visually assessed. For the mixture tested the
results are listed in table 2. In this test the compound I-2, and
orysastrobin, and
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine (compound 2.2), and
N-[2-(1,1,2,3,3,3-hexafluoropropoxy)-phenyl]-3-difluoromethyl-1-methyl-1H-
-pyrazole-4-carboxamide (compound 3.1), were used.
[0331] Following results were obtained:
TABLE-US-00006 Green Peach Aphid ppm Average Control % I-2 0.5 0
orysastrobin 40 0 pyraclostrobin 8 0 2.2 8 0 3.1 1000 0 I-2 +
orysastrobin 0.5 + 40 50* I-2 + pyraclostrobin 0.5 + 8 75* I-2 +
2.2 0.5 + 8 75* I-2 + 3.1 0.5 + 1000 100* *synergistic control
effect according to Colby's equation
* * * * *
References