Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-12-10
2004-03-02
Qazi, Sabiha (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S263000, C514S538000, C514S539000, C514S552000, C514S217060, C514S619000, C514S210210, C425S405100
Reexamination Certificate
active
06699874
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent and synergistically effective amounts of
(a) at least one azolopyrimidine of formula I
in which
R
1
represents a C
1-6
alkyl, C
3-6
alkenyl or C
1-6
haloalkyl group, or
R
2
represents a hydrogen atom or a C
1-6
alkyl group, or
R
1
and R
2
taken together represent a C
1-6
alkylene group,
L
1
represents a halogen atom;
L
2
and L
3
each independently represent a hydrogen or a halogen atom; and
and at least one fungicidal active ingredient selected from the following classes (A), (B) and (C):
(A) a compound selected from the group consisting of benomyl, carboxin, captan, chlorothalonil, copper oxychloride, cyprodinil, dimethomorph, dithianon, dodine, famoxadone, fenpiclonil, fenpropimorph, fluazinam, mancozeb, metalaxyl, pyrimethanil, quinoxifen, sulfur, triforine and vinclozolin;
(B) a fungicidal triazole derivative; and
(C) a synthetic strobilurine derivative.
The fungicidal compounds of formula I to be used according to the present invention are known from U.S. patent U.S. Pat. No. 5,593,996. The compounds of the classes (A) and (B) are known from “The Pesticide Manual”, 11
th
edition (1997), Editor Clive Tomlin. Fenhexamid is known from AGROW No. 287, p. 21. The synthetic strobilurines are known, for example, from WO 92/08703, EP 0 253 213 and EP 0 398 692.
However, none of the above mentioned prior art references teaches a combination of compounds of formula I with any of the fungicidal active ingredients selected from the classes (A), (B) and (C) as described above, nor that such mixtures show synergistic effects and can advantageously be used for controlling diseases such as wheat powdery mildew, barley powdery mildew, wheat leaf rust, barley net blotch and wheat Septoria leaf blotch, Botrytis diseases and others.
Surprisingly, when compounds of formula I were tank mixed with compounds from classes (A), (B) and (C) and used in greenhouse and field trials, a synergistic increases in activity were observed, compared to the activity expected based on the activities of the individual active ingredients.
A mixture of fungicides shows synergistic effect if the fungicidal activity of the mixture is larger than the sum of activities of the separately applied compounds. The expected fungicidal activity for a given mixture of two fungicides can also be calculated as follows (See Colby, S. R., “Calculating synergistic and antagonistic response of herbicide combinations”, Weeds 15, pp 20-22 (1967):
EE=x+y−x·y
/100
wherein
x is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient A at a dose rate a;
y is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient B at a dose rate b;
EE is the expected efficacy with a combination of fungicidal active ingredients A and B at a dose of a+b, respectively.
If the actual efficacy (E) exceeds the expected (calculated) one (EE), the mixture displays a synergistic effect.
SUMMARY OF THE INVENTION
The present invention includes a fungicidal composition comprising an acceptable carrier and/or surface active agent and synergistically effective amounts of at least one compound of formula I, and at least one fungicidal active ingredient selected from the following classes (A), (B) and (C):
(A) a compound selected from the group consisting of benomyl, carboxin, captan, chlorothalonil, copper oxychloride, cyprodinil, dimethomorph, dithianon, dodine, famoxadone, fenpiclonil, fenpropimorph, fluazinam, mancozeb, metalaxyl, pyrimethanil, quinoxifen, sulfur, triforine and vinclozolin;
(B) a fungicidal triazole derivative; and
(C) a synthetic strobilurine derivative.
The present invention also includes a method of controlling the growth of phytopathogenic fungi at a locus which comprises applying synergistically effective amounts of at least one azolopyrimidine of formula I and at least one fungicidally active ingredient selected from classes (A), (B) and (C) defined above to the locus.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred compounds of formula I are those wherein
R
1
and R
2
together with the interjacent nitrogen atom represent a 4-methylpiperidine ring, or wherein
R
1
represents a C
1-6
alkyl, in particular an isopropyl group, a C
1-6
haloalkyl, in particular a 2,2,2-trifluoroethyl or a 1,1,1-trifluoroprop-2-yl group, or a C
3-8
cycloalkyl group, in particular a cyclopentyl or cyclohexyl group and R
2
represents a hydrogen atom, and/or
wherein L
1
represents a fluorine or chlorine atom and L
2
and L
3
each independently represent a hydrogen atom or a fluorine atom, in particular
wherein L
1
represents fluorine, L
2
represents hydrogen and L
3
represents chlorine or wherein L
1
through L
3
represent fluorine.
Particularly preferred are the following azolopyrimidines: 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine A, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine B and 5-chloro-6-(2,4,6-trifluorophenyl)-7-(1,1,1-trifluoroprop-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine C. Azolopyrimidine C due to the chirality of its 1,1,1-trifluoroprop-2-yl group may be applied as a racemic mixture or in the form of an enantiomeric enriched compound, in particular as (S)-enantiomer coded (S)-Azolopyrimidine C.
Preferred triazole derivatives in the practice of this invention are the compounds of formula II,
wherein
L represents a linking group selected from the groups (a), (b), (c) and (d)
in which
X
1
represents an alkyl or an optionally substituted phenyl group;
X
2
and X
3
each independently represent a hydrogen atom or an alkyl group;
X
4
represents an alkyl or cyclopropylalkyl group;
q is 1 or 2; and
n is 0 or 2.
Particularly preferred are the triazoles selected from the group consisting of cyproconazole, epoxiconazole, metconazole, propiconazole and tebuconazole.
Preferred strobilurine derivatives in the practice of this invention are the compounds of formula III,
wherein
A represents N or CH;
B represents a —O—, —OCH
2
—, a —CH
2
O—, a pyrimid-4,6-dioxydiyl group or a group of formula
R
3
represents a C
1-4
alkyl group;
R
4
represents a C
1-6
alkoxy or a C
1-6
alkylamino group;
R
5
represents a hydrogen or halogen atom or a cyano, a C
1-4
alkyl or a C
1-4
haloalkyl group; and
m is 0, 1 or 2;
in particular azoxystrobin, kresoxim methyl, CGA-279202 (AGROW 279, p.17 1998) or SSF126 (Pesticide Manual, loc. cit., page 1114)
Preferred compositions of this invention comprise the following constituents:
a carrier agent;
at least one azolopyrimidine of formula I,
at least one compound selected from the classes (A), (B) and (C) as defined above;
optionally an adjuvant selected from the group consisting of polyalkoxylated alcohols, triglycerides and amines, in particular Synperonic 91-6, which is commercially available from ICI Surfactants;
optionally a foam breaking agent, in particular a mixture of perfluoroalkyphosphonic acids and/or perfluoroalkylphosphinic acids, in particular Defoamer SF or Fluowett PL, which are commercially available from Clariant GmbH.
The compound of formula I and the compound selected from the classes (A), (B) and (C) as defined above are to be applied together, in synergistically effective amounts. These synergistic mixtures exhibit an extraordinary efficacy against a broad range of phytopathogenic fungi, in particular against fungi from the classes ascomycetes, basidiomycetes, oomycetes and deuteromycetes. Therefore, they can be applied advantageously against a broad range of diseases in different crops. They may be applied as leaf, stem, root, into-water, seed dressing, nursery box or soil fungicides.
The composition according to the invention may be preferably applied for contro
Cotter Henry Van Tuyl
May Leslie
Reichert Gunter
Sieverding Ewald
Keil & Weinkauf
Qazi Sabiha
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