Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-09-09
2001-07-31
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S521000
Reexamination Certificate
active
06268371
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
and R
2
each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or
R
1
and R
2
together with the adjacent nitrogen atom represent an optionally substituted heterocyclic ring,
R
3
represents a hydrogen or a halogen atom or an alkyl group,
R
4
represents hydrogen or an alkyl or aryl group,
L represents a halogen atom or an optionally substituted alkyl or alkoxy group,
A represents N or CR
5
, wherein R
5
has the meaning given for R
4
, and
n is 0 or an integer between 1 and 5; and
(b) and at least one fungicidal active ingredient which is capable of inhibiting the melanin biosynthesis in particular in
Pyricularia oryzae
the causal agent of the rice blast disease.
The fungicidal compounds of formula I are known from U.S. Pat. No. 4,567,263 and U.S. Pat. No. 5,593,996.
The class of melanin biosynthesis inhibitors (MBI) are chemical compounds which are capable of diminishing the in-vivo synthesis of melanin by inhibiting any of the reductase and/or dehydratase enzymes which are responsible for converting tetrahydroxynaphthalene into dihydroxynaphthalene. This class of compounds includes the following known compounds: carpropamid, chlobenthiazione, diclocymet, pyroquilon, phthalide, tricyclazole and certain phenoxyamides, which are known for example from EP 0 262 393 and Japanese patent application JP 5-9165-A.
However, there is no hint to combine the compounds of formula I, with a MBI. Moreover, there is no hint that such mixtures can be advantageously be used for controlling rice diseases such as rice blast and rice sheath blight and others.
Surprisingly, a strong synergy between the compounds of formula I and MBIs in field trials was found when these two compounds were in-tank mixed and when the activity of these co-formulations was compared with that of the solo formulations of each active ingredient.
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 melanin biosynthesis inhibitor (MBI).
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 MBI to the locus.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred compounds of formula I include those wherein
R
1
and R
2
together with the interjacent nitrogen atom represent an optionally substituted 6-membered heterocyclic ring, in particular 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 or a C
1-6
alkyl group and/or wherein
wherein L
1
represents a halogen atom, preferably flourine or chlorine and L
2
and L
3
each independently represent a hydrogen atom or a halogen atom, preferably fluorine, 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 and/or wherein
Hal represents a chlorine atom.
In a particularly preferred embodiment the azolopyrimidine is the compound of formula IA
wherein L and n have the meaning given for formula I, and
R
1
represents an alkyl or haloalkyl group,
R
2
represents a hydrogen atom, or
R
1
and R
2
together represents an optionally substituted alkylene group having 3 to 6 carbon atoms in the main chain, in which one CH
2
group may be replaced by O or NH, and
Hal denotes a halogen atom.
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-isopropylamino-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine B, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine coded Azoloyrimidine C 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 D.
Preferred MBIs include carpropamid, chlobenthiazione, dicyclocymet, pyroquilon, phthalide and tricyclazole.
Furthermore, the phenoxyamides of formula 11 are preferred MBIs:
wherein
R
5
and R
6
each independently represent a hydrogen atom or an optionally substituted alkyl group;
R
7
independently represents a hydrogen atom or an optionally substituted alkyl group
R
8
and R
9
each independently represent a hydrogen atom or an optionally substituted alkyl or alkenyl group; or R
8
and R
9
together may represent an alkylene group;
Y each independently represents a halogen atom or an optionally substituted alkyl or alkenyl group or a cyano or nitro group;
m is 0 or an integer of 1, 2, 3 or 4.
Particularly preferred phenoxyamides are the compounds of formula IIA
wherein R
9
, Y and m have the meaning given, in particular wherein
in which Y′ represents a hydrogen atom or a methyl group and/or wherein
R
9
represents a C
1-8
-alkyl group.
Most preferred are N-(1-cyano-1,2-dimethyl-propyl)-2-(2,4-dichlorophenoxy)-propionamide, in particular a mixture of (2R)-and (2R/S)-N-(1-cyano-1,2-dimethyl-propyl)-2-(2,4-dichlorophenoxy)-propionamide coded Propionamide E and N-(1-cyano-1-ethyl-propyl)-2-(2,4-dichloro-3-methylphenoxy)-propionamide coded Propionamide F.
Preferred formulations of this invention include those comprising the following constituents:
a carrier agent;
at least one azolopyrimidine of formula I,
at least one MBI, in particular a phenoxyamide of formula II,
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 MBI 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 and deuteromycetes. Therefore, they can be applied advantageously against rice diseases. They are systemic and may be applied as leaf, into water, seed dressing, nursery box or soil fungicides.
The mixture according to the invention may be preferably applied for controlling phytopathogenic fungi of the genera: Pyricularia, Rhizoctonia, Cochliobolus, Cercospora, Magnaporthe, Alternaria, Drechslera, Fusarium, Gerlach
May Leslie
Sieverding Ewald
American Cyanamid Co.
Maurer Barbara V.
Robinson Allen J.
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