Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-09-21
2001-02-27
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...
C514S407000
Reexamination Certificate
active
06194417
ABSTRACT:
THE PRESENT INVENTION RELATES TO A FUNGICIDAL MIXTURE WHICH COMPRISES
a) an oxime ether of the formula I
where the substituents have the following meanings:
X is oxygen or amino (NH);
Y is CH or N;
Z is oxygen, sulfur, amino (NH) or C
1
-C
4
-alkylamino (N-C
1
-C
4
-alkyl);
R′ is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
3
-C
6
-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkylthio;
and/or
b) a carbamate of the formula II
where T is CH or N, n is 0, 1 or 2 and R is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, it being possible for the radicals R to be different when n is 2, and
c) (±)-(2-chlorophenyl)(4-chlorophenyl)(pyrimidin-5-yl)methanol III
in asynergistically active amount.
Moreover, the invention relates to methods of controlling harmful fungi with mixtures of the compounds I and II and to the use of the compound I and the compound II for the preparation of such mixtures.
The compounds of the formula I, their preparation and their action against harmful fungi have been disclosed in the literature (WO-A 95/21,153, WO-A 95/21,154, DE-A 195 28 651.0).
Compounds of the formula II, their preparation and their action against harmful fungi have been described in WO-A 96/01,256 and WO-A 96/01,258.
The compound III (GB-A 1,218,623; common name: fenarimol), its preparation and its action against harmful fungi is also disclosed.
It was an object of the present invention to provide mixtures which have an improved activity gainst harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures) with a view to reducing the rates of application and to improving the spectrum of action of the known compounds.
Accordingly, we have found that this object is achieved by the mixture defined at the outset. Moreover, we have found that better control of the harmful fungi is possible by applying the compounds I and/or II and the compound III simultaneously together or separately or by applying the compounds I and/or II and the compound III in succession than when the individual compounds are used.
The invention covers binary mixtures of compounds I and III or II and III as well as mixtures of compounds I, II and III.
In particular, the general formula I represents oxime ethers in which X is oxygen and Y is CH or X is amino and Y is N.
Moreover, preferred compounds I are those where Z is oxygen.
Equally, preferred compounds I are those where R′ is alkyl or benzyl.
Especially preferred with a view to their use in the synergistic mixtures according to the invention are the compounds I compiled in the tables which follow:
TABLE 1
Compounds of the formula IA where ZR′ for each compound
corresponds to one row of Table A
(IA)
TABLE 2
Compounds of the formula IB where ZR′ for each compound
corresponds to one row of Table A
(IB)
TABLE A
No.
ZR′
I.1
O—CH
2
CH
2
CH
3
I.2
O—CH(CH
3
)
2
I.3
O—CH
2
CH
2
CH
2
CH
3
I.4
O—CH(CH
3
)CH
2
CH
3
I.5
O—CH
2
CH(CH
3
)
2
I.6
O—C(CH
3
)
3
I.7
S—C(CH
3
)
3
I.8
O—CH(CH
3
)CH
2
CH
2
CH
3
I.9
O—CH
2
C(CH
3
)
3
I.10
O—CH
2
C(Cl)═CCl
2
I.11
O—CH
2
CH═CH—Cl (trans)
I.12
O—CH
2
C(CH
3
)═CH
2
I.13
O—CH
2
-(cyclopropyl)
I.14
O—CH
2
—C
6
H
5
I.15
O—CH
2
—[4-F—C
6
H
4
]
I.16
O—CH
2
CH
3
I.17
O—CH(CH
2
CH
3
)
2
In relation to the C═Y double bond, the compounds of the formula I can be in the E or the Z configuration (in relation to the carboxylic acid function). Accordingly, they can be used in the mixture according to the invention in each case either in the form of the pure E or z isomers or else in the form of an E/Z isomer mixture. The E/Z isomer mixture or the E isomer are preferably used in each case, the E isomer of the compound I being especially preferred.
The C═N double bonds of the oxime ether groups in the side chain of the compounds I can be in each case in the form of pure E or Z isomers or in the form of E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention as isomer mixtures or else as pure isomers. With a view to their use, compounds I which are particularly preferred are those where the terminal oxime ether group of the side chain is in the cis configuration (OCH
3
group in relation to ZR′).
Due to the basic character, the compounds I, II and III are capable of forming adducts or salts with inorganic or organic acids or with metal ions.
In particular, the formula II represents carbamates in which the combination of the substituents corresponds to one row of the table which follows:
TABLE 3
No.
T
R
n
II.1
N
2-F
II.2
N
3-F
II.3
N
4-F
II.4
N
2-Cl
II.5
N
3-Cl
II.6
N
4-Cl
II.7
N
2-Br
II.8
N
3-Br
II.9
N
4-Br
II.10
N
2-CH
3
II.11
N
3-CH
3
II.12
N
4-CH
3
II.13
N
2-CH
2
CH
3
II.14
N
3-CH
2
CH
3
II.15
N
4-CH
2
CH
3
II.16
N
2-CH(CH
3
)
2
II.17
N
3-CH(CH
3
)
2
II.18
N
4-CH(CH
3
)
2
II.19
N
2-CF
3
II.20
N
3-CF
3
II.21
N
4-CF
3
II.22
N
2,4-F
2
II.23
N
2,4-Cl
2
II.24
N
3,4-Cl
2
II.25
N
2-Cl, 4-CH
3
II.26
N
3-Cl, 4-CH
3
II.27
CH
2-F
II.28
CH
3-F
II.29
CH
4-F
II.30
CH
2-Cl
II.31
CH
3-Cl
II.32
CH
4-Cl
II.33
CH
2-Br
II.34
CH
3-Br
II.35
CH
4-Br
II.36
CH
2-CH
3
II.37
CH
3-CH
3
II.38
CH
4-CH
3
II.39
CH
2-CH
2
CH
3
II.40
CH
3-CH
2
CH
3
II.41
CH
4-CH
2
CH
3
II.42
CH
2-CH(CH
3
)
2
II.43
CH
3-CH(CH
3
)
2
II.44
CH
4-CH(CH
3
)
2
II.45
CH
2-CF
3
II.46
CH
3-CF
3
II.47
CH
4-CF
3
II.48
CH
2,4-F
2
II.49
CH
2,4-Cl
2
II.50
CH
3,4-Cl
2
II.51
CH
2-Cl, 4-CH
3
II.52
CH
3-Cl, 4-CH
3
The compounds II.12, II.23, II.32 and II.38 are especially preferred.
REFERENCES:
patent: 1 218 623 (1971-01-01), None
patent: 9601256 (1996-01-01), None
Pesticide Sci.,BD 44, N4. 1, May 1995, 77-79.
Research Disclosure No. 348 (1993).
Ammermann Eberhard
Bayer Herbert
Leyendecker Joachim
Lorenz Gisela
Mappes Dietrich
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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