Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-05-15
2001-08-14
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...
C514S259500
Reexamination Certificate
active
06274586
ABSTRACT:
The present invention relates to compositions for controlling harmful fungi and to methods of controlling harmful fungi using such compositions.
The literature discloses that active ingredients which inhibit the cytochrome bc
1
conplex (cytochrome complex III) can be employed as fungicides [cf. U. Brandt, U. Haase, H. Schägger, G. von Jagow: “Spezifität und Wirkmechanismus der Strobilurine” (specificity and Mechanism of Action of the Strobilurins), Dechema Monograph Vol. 129, 27-38, V C H Verlagsgesellschaft Weinheim, 1993; J. M. Clough: Natural Product Reports, 1993, 565-574; F. Röhl, H. Sauter: Biochem. Soc. Trans. 22, 635 (1993)].
However, when using these active ingredients as fungicides, it has emerged that their activity is only transient, i.e. that renewed growth of the fungi was observed after a short time.
It is therefore an object of the present invention to provide an improved possibility of controlling harmful fungi, in particular botrytis.
Surprisingly, we have found that this object is achieved by a composition which comprises an active ingredient which inhibits respiration on the cytochrome complex III in combination with fenazaquin, which is known as being acaricidally active (cf. The Pesticide Manual, 10th Edition, 1994; CAS reg. No. 120928-09-8).
The present invention therefore relates to compositions for controlling harmful fungi which comprise, in a solid or liquid carrier,
a) at least one active ingredient I, which inhibits respiration on the cytochrome complex III, and
b) fenazaquin, of the formula
The active ingredient I is preferably a compound of the formula. IA or IB:
where . . . is a double or single bond;
R′ is —C[CO
2
CH
3
]═CHOCH
3
, —C[CO
2
CH
3
]═NOCH
3
, —C[CONHCH
3
]═NOCH
3
, —C[CO
2
CH
3
]═CHCH
3
, —C[CO
2
CH
3
]═CHCH
2
CH
3
, —C[COCH
3
]═NOCH
3
, —C[COCH
2
CH
3
]═NOCH
3
, —N(OCH
3
)—CO
2
CH
3
, —N(CH
3
)—CO
2
CH
3
or —N(CH
2
CH
3
)—CO
2
CH
3
;
R″ is an organic radical which is bonded directly or via an oxy, mercapto, amino, or alkylamino group, or together with a group X and the ring Q or T to which they are bonded can contain an unsubstituted or substituted bicyclic, partially or fully unsaturated system which, besides carbon ring members, can have 1, 2 or 3 hetero atoms independently selected from amongst oxygen, sulfur and nitrogen;
R
x
is —OC[CO
2
CH
3
]═CHOCH
3
, —OC[CO
2
CH
3
]═CHCH
3
, —OC[CO
2
CH
3
]═CHCH
2
CH
3
, —SC[CO
2
CH
3
]═CHOCH
3
, —SC[CO
2
CH
3
]═CHCH
3
, —SC[CO
2
CH
3
]═CHCH
2
CH
3
, —N(CH
3
)C[CO
2
CH
3
]═CHOCH
3
, —N(CH
3
)C[CO
2
CH
3
]═NOCH
3
, —CH
2
C[CO
2
CH
3
]═CHOCH
3
, —CH
2
C[CO
2
CH
3
]═NOCH
3
or —CH
2
C[CONHCH
3
]═NOCH
3
;
R
y
is oxygen, sulfur, ═CH— or ═N—;
n is 0, 1, 2 or 3, it being possible for the radicals X to be identical or different if n>1;
X is cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, or, if n>1, a C
3
-C
5
-alkylene, C
3
-C
5
-alkenylene, oxy-C
2
-C
4
-alkylene, oxy-C
1
-C
3
-alkyleneoxy, oxy-C
2
-C
4
-alkenylene, oxy-C
2
-C
4
-alkenyleneoxy or butadienediyl group which is bonded to two adjacent C atoms of the phenyl ring, it being possible for these chains, in turn, to have attached to them one to three radicals which, independently of one another, are selected from amongst halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio;
Y is═C— or —N—;
Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridinyl, pyrimidinyl or triazinyl; and
T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl or triazinyl.
The substituent R″ is, in particular, an alkyl, alkenyl, alkynyl, aryl, hetaryl, arylalkyl, hetarylalkyl, arylalkenyl, hetarylalkenyl, arylalkynyl or hetarylalkynyl radical which may be interrupted by one or more groups selected from amongst O, S, SO, SO
2
, NR (R═H or alkyl), CO, COO, OCO, CONH, NHCO and NHCONH, or a radical of the formulae which are as defined below CH
2
ON═CR
&agr;
CR
&bgr; or CH
2
ON═CR
8
CR
&dgr;
═NOR
&egr;
. These radicals may also have one or more (preferably 1, 2 or 3) substituents which, independently of one another, are selected from amongst alkyl, alkoxy, halogen, haloalkyl (in particular CF
3
and CHF
2
) and aryl. The latter, in turn, can have, 1, 2 or 3 substituents which, independently of one another, are selected from amongst halogen, haloalkyl (in particular CF
3
and CHF
2
), phenyl, CN and phenoxy.
Such compounds and their preparation are described in the literature given in Tables I.1 to I.8 below. Compounds which are not described in these tables can be prepared by similar methods.
Halogen within the scope of the present invention is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
The term “alkyl” encompasses straight-chain and branched alkyl groups. They are preferably straight-chain or branched C
1
-C
12
-alkyl and in particular C
1
-C
6
-alkyl groups. Examples of alkyl groups are alkyl such as, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl.
Haloalkyl is an alkyl group as defined above which is partially or fully halogenated by one or more halogen atoms, in particular fluorine and chlorine. There are preferably 1 to 3 halogen atoms present, the difluoromethyl or trifluoromethyl group being specially preferred.
What has been said above for the alkyl group and haloalkyl group applies analogously to the alkyl and haloalkyl group in alkoxy, haloalkoxy, alkylthio and haloalkylthio or similar groups.
The alkenyl group encompasses straight-chain and branched alkenyl groups. They are preferably straight-chain or branched C
3
-C
12
-alkenyl groups, in particular C
3
-C
6
-alkenyl groups. Examples of alkenyl groups are 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 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-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 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, 1,1-dimethyl-3-butenyl
,
1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, in particular 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl.
The alkenyl group can be partially or fully halogenated by one or more halogen atoms, in particular fluorine and chlorine. It has preferably 1 to 3 halogen atoms.
The alkynyl group encompasses straight-chain and branched alkynyl groups. They are preferably straight-chain or branched C
3
-C
12
-alkynyl groups, in particular C
3
-C
6
-alkynyl groups. Examples of alkynyl groups are 2-propynyl, 2-butynyl, 3-butynyl,
Ammermann Eberhard
Bayer Herbert
Kohle Harald
Lorenz Gisela
Retzlaf Günter
BASF - Aktiengesellschaft
Keil & Weinkauf
Qazi Sabiha
LandOfFree
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