Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-01-29
2002-02-12
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...
C514S538000, C514S539000, C514S546000, C514S552000, C514S687000
Reexamination Certificate
active
06346535
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 benzophenone of formula I
wherein
R
1
represents a halogen atom, an optionally substituted alkyl, alkanoyloxy or alkoxy group; or a hydroxy group,
R
2
represents a halogen atom or an optionally substituted alkyl group,
R
3
independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or a nitro group;
m is 0 or an integer of 1 to 3;
R
4
represents a halogen atom, a cyano, carboxy, hydroxy or nitro group or an optionally substituted alkyl, alkoxy, alkenyl, alkylthio, alkylsulphinyl, alkylsulphonyl or amino group;
R
5
represents an optionally substituted alkyl group;
R
6
represents a halogen atom or a nitro group, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, aryloxy group;
R
7
independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkoxy group;
n is 0 or 1; and
(b) at least one fungicidally active ingredient selected from the group consisting of (A), (B), (C), (D) and (E) wherein
(A) is an ergosterol biosynthesis inhibitor;
(B) is a strobilurine derivative,
(C) is a melanin biosynthesis inhibitor,
(D) is a compound selected from the group consisting of acibenzolar, benomyl, captan, carboxin, chlorothalonil, copper, cyprodinil, dinocap, dithianon, dimethomorph, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb, metalaxyl, pyrifenox, sulfur and vinclozolin, and
(E) is an azolopyrimidine of formula II
wherein
R
8
and R
9
each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or
R
8
and R
9
together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring,
R
10
represents hydrogen or an alkyl or aryl group,
R
11
represents a hydrogen or halogen atom or an alkyl or alkoxy group,
L independently represents a halogen atom or an optionally substituted alkyl or alkoxy group,
p is 0 or an integer from 1 to 5; and
A represents N or CR
12
, wherein R
12
has the meaning given for R
10
.
The fungicidal compounds of formula I utilized in the present invention are disclosed in U.S. Pat. No. 5,773,663.
The compounds of the classes (A), (B) and (D) are disclosed in The Pesticide Manual 11
th
edition 1997, edited by C. Tomlin (British Crop Protection Council).
The class of melanin biosynthesis inhibitors (MBI) (C) 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, in particular AC 382042, which are discussed, for example, in EP 0 262 393, and Japanese patent application JP 5-9165-A.
The fungicidal compounds of formula II utilized in the present invention are disclosed in U.S. Pat. No. 5,593,996 and International Patent Applications WO 98/46607 and WO 98146608.
U.S. Pat. No. 5,773,663 suggests combinations of fungicidal benzophenone derivatives with other fungicides such as 4,6-dinitro-o-cresol, benalaxyl, benomyl, captafol, captan, carbendazim, chlorothalonil, copper, cymoxanil, dichlofluanid, dichlone, difenoconazole, dimethomorph, diniconzole, dinocap, dithianon, fenpiclonil, fenpropiomorph, hymaxazol, imazalil, iprodione, isoprothiolane, kasugamycin, mancozeb, mepronil, mercuric oxide, oxadixyl, oxolinic acid, penconazole, propineb, pyrifenox, thiabendazole, thiram, tolclofos-methyl, triadimefon, triflumizole, triforine validamycin A, vinclozolin, zineb and ziram.
However, there is no suggestion that such mixtures show synergistic effects and can advantageously be used for controlling diseases such as wheat powdery mildew, wheat leaf rust and wheat Septoria leaf blotch, Botrytis diseases and others.
Surprisingly, a strong synergy between the compounds of formula I and the fungicidally active ingredients selected from the classes (A), (B), (C), (D) and (E) as described above in greenhouse and field trials was found when these two compounds were in-tank mixed and when the activity of these mixtures was compared with that of the solo activity of each active ingredient.
A mixture of fungicides shows synergistic effect if the actual (observed) fungicidal activity from the mixture is greater than the expected activity based on the activities when each fungicide is applied separately. A standard method for calculating the expected fungicidal activity for a given mixture of two fungicides is as follows:
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 group consisting of (A), (B), (C), (D) and (E) wherein
(A) is an ergosterol biosynthesis inhibitor;
(B) is a strobilurine derivative,
(C) is a melanin biosynthesis inhibitor,
(D) is a compound selected from the group consisting of acibenzolar (BION), benomyl, captan, carboxin, chlorothalonil, copper, cyprodinil, dinocap, dithianon, dimethomorph, dodine, ethirimol, famoxadone, fenpiclonil, fluazinam, mancozeb, metalaxyl, pyrifenox, sulfur and vinclozolin, and
(E) is an azolopyrimidine of formula II.
The present invention also includes a method of controlling the growth of phytopathogenic fungi at a locus which comprises applying to the locus synergistically effective amounts of at least one benzophenone of formula I and at least one fungicidally active ingredient selected from the group consisting of (A), (B), (C), (D) and (E) as defined above.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred compounds of formula I for use in the compositions and methods of the present invention are the benzophenones of formula IA,
wherein
R
1
represents a halogen atom, a methyl, trifluoromethyl, methoxy or hydroxy group, in particular, a chlorine atom, a methyl or methoxy group;
R
2
represents a halogen atom, in particular, a chlorine atom or a methyl group;
R
3
represents a bromine or chlorine atom, a methyl, trifluoromethyl or nitro group, in particular, a bromine atom;
n is 0 or 1
R
4
represents a methyl group;
R
5
represents an alkyl group, in particular, a methyl group; and
R
6
and R
7
each independently represent an alkoxy group which may be substituted by a phenyl, alkylphenyl or halophenyl group, preferably C1-6 alkoxy being optionally substituted by a phenyl, methylphenyl or fluorophenyl group, in particular methoxy, benzyloxy and 2-fluorobenzyloxy.
Particularly preferred are the benzophenones selected from the group consisting of 6′-butoxy-2,6-dichloro-4′,5′-dimethoxy-2′-methylbenzophenone (hereinafter coded BP-1), 2,6-dichloro-4′,5′-dimethoxy-6′-(2-fluorobenzyloxy)-2′-methylbenzophenone (hereinafter coded BP-2), 6′-benzyloxy-4,5′-dimethoxy-2,6-dimethyl-2′-methylbenzophenone (hereinafter coded BP-3); 5-bromo-2′,6-dimethyl-2,4′,5′,6′-tetramethoxybenzophenone (hereinafter coded BP
Cotter Henry Van Tuyl
Emanuel Jegerings Petrus Martinus Franciscus
Reichert Gunther
Sieverding Ewald
American Cyanamid Company
Costello Charles F.
Robinson Allen J.
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