Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Reexamination Certificate
2001-02-13
2004-02-24
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
C514S479000, C514S484000, C514S487000
Reexamination Certificate
active
06696497
ABSTRACT:
DESCRIPTION
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; alkoxy group or a hydroxy group;
R
2
represents a halogen atom or an optionally substituted alkyl group,
m is 0 or an integer of 1 to 3;
R
3
independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or a nitro group;
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;
n is 0 or 1; and
R
7
independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkoxy group; and
(b) at least one valinamid of formula II
in which
R
8
represents alkyl and
Ar represents Aryl or hetaryl, whereby
aryl represents a phenyl or napthyl moiety,
and
heteroaryl represents a benzthiazolyl, benzimidazolyl or benzoxazoyl moiety,
where if desired, these aromatic radicals can carry one to three substituents selected from the group consisting of halogen, C
1-6
alkyl and C
1-6
alkoxy.
The fungicidal compounds of formula I to be used according to the present invention are known for example from U.S. Pat. No. 5,773,663. In addition, U.S. Pat. No. 5,773,663 suggests to combine fungicidal benzophenone derivatives with other fungicides.
However, there is no hint that such mixtures show synergistic effects and can advantageously be used for controlling diseases such as grape downy mildew or others. The fungicidal compounds of formula 11 are known for example from EP 0 472 996, DE-A 43 21 897, WO-A 96 07638, DE 1 9531 814 and JP-A 09 323984.
Although mixtures comprising either benzophenones of formula I (EP 1023834) or valinamides of formula II (WO 99 56551) as active ingredients are described, mixtures comprising both benzophenones and valinamides have not been described yet.
Surprisingly, a strong synergy between the compounds of formula I and the compounds of formula II in greenhouse 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 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.
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 compound of formula II.
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 benzophenone of formula I and at least one compound of formula II as defined above to the locus.
All moieties mentioned for the substituents R
1
to R
7
of formula I as well as R
8
and the substituents of the Aryl moiety of formula II, R
9
and R
10
are collective terms for individual enumeriations of the individual members of a group. For all alkyl moieties and the alkyl moieties of alkoxy, alkanoyloxy, alkylthio, alkylsulfonyl and alkylsulfinyl a C
1-6
alkyl moiety is preferred. For all alkenyl moieties or the alkenyl moieties of alkenyloxy a C
2-6
alkenyl moiety is preferred. For all alkynyl moieties or the alkynyl moieties of alkynyloxy a C
2-6
alkynyl moiety is preferred. For all cycloalkyl moieties or the cycloalkyl moieties of cycloalkyloxy a C
3-8
alkyl moiety is preferred.
For example
halogen is fluorine, chlorine, bromine and iodine;
alkyl is straight-chain or branched alkyl groups having 1 to 6 carbonatoms such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
C
3-6
cycloalkyl or the cycloalkyl moiety of cycloalkoxy is a monocyclic alkyl groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
C
2-6
alkenyl is a straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl- 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1 -ethyl-2-butenyl, 1 -ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
C
2-6
alkynyl is a straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any desired position, such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
aryl or aryloxy is an aromatic mono- or polycyclic hydrocarbon radical which is bonded to the structure directly or (aryloxy)
Reichert Gunter
Sieverding Ewald
BASF - Aktiengesellschaft
Keil & Weinkauf
Pak John
LandOfFree
Fungicidal mixtures does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fungicidal mixtures, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fungicidal mixtures will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3355012