Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Reexamination Certificate
2000-01-18
2003-09-02
Killos, Paul J. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
C514S682000, C560S255000, C568S333000
Reexamination Certificate
active
06613806
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention concerns the enhancement of the efficacy of fungicidal benzoylbenzenes by addition of certain adjuvants, preparations through which this effect can be exploited as well as the combined use of these adjuvants and the fungicidal benzoylbenzenes in the control of phytopathogenic fungi and the plant diseases they cause.
As a rule inert ingredients must be used to bring crop protection agents, for example fungicidal compounds, into such a form that the user can apply them either as such or after dilution with water. The right choice of formulation type and of inert ingredients for that formulation type such as carriers for the formulation often determines to a significant extent whether the active ingredient can display its full efficacy on application.
The efficacy of the active components can often be improved by addition of other (active) ingredients. The observed efficacy of the combination of ingredients can sometimes be significantly higher than that would be expected from the amounts of the individual ingredients used (synergism).
The usual components of formulations such as carriers and inert ingredients (e.g. organic solvents, suspension agents, emulgators, wetting agents, solubilizing agents) which do not themselves possess pesticidal activity, however, do not usually lead to an unexpected increase in efficacy.
EP 0 727 141-A discloses fungicidal benzoylbenzenes compounds.
However, although these compounds are effective fungicides when applied to plants in conventional formulations it is desirable economically and environmentally to provide a means to lower the dose required for effective disease control.
SUMMARY OF THE INVENTION
The present invention relates to a method for the enhancement of the activity and/or systemicity of fungicidal compositions containing at least one benzoylbenzene 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, an optionally substituted alkyl group,
R
3
represents a halogen atom or an optionally substituted alkyl group,
m is 0 or an integer of 1 to 3;
R
4
independently represents a halogen atom, an optionally substituted alkyl or alkoxy group or a nitro group;
R
5
represents an optionally substituted alkyl group;
R
6
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
7
represents a halogen atom or a nitro group, an optionally substituted alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyl, cycloalkyloxy, aryloxy group; and
n is 0, 1 or 2;
characterized in that one or more adjuvants selected from the group consisting of
(a) alkylpolyglycosides, alkenyl succinic acid derivatives, dialkyl sulfosuccinates, polyvinylpyrrolidones, perfluoroalkyl acids derivatives, perfluoro(C
3-30
)alkyl esters of carboxylic acids, and mixtures thereof;
(b) alkoxylated alcohols, amines or acids;
(c) water-immiscible polar aprotic solvents;
are added to the said composition.
Furthermore, the compositions used according to the present invention also expand the efficacy profile of the said benzoylbenzenes in so far as they can be successfully applied according to the present invention, with reduced application amounts, against fungal diseases for both curative and residual control.
Those and other objects and features of the invention will become more apparent from the detailed description set forth hereinbelow.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has now been found that, surprisingly, the effective amounts of fungicidal benzoylbenzenes of formula I which must be applied can be lowered considerably, with respect to the amounts usually required to achieve the same fungicidal effect, if these fungicidal compounds or their formulations are applied in combination with certain adjuvants selected from the group consisting of
(a) alkylpolyglycosides, alkenyl succinic acid derivatives, dialkyl sulfosuccinates, polyvinylpyrrolidones, perfluoroalkyl acids derivatives, perfluoro(C
3-20
)alkyl esters of carboxylic acids, and mixtures thereof;
(b) alkoxylated alcohols, amines or acids; and
(c) water-immiscible polar aprotic solvents.
The biological activity of the active ingredient of formula I can be increased by including any of these adjuvants in the spray dilution or directly in the formulation. An adjuvant is defined here as a substance which can increase the biological activity of an active ingredient but is not itself significantly biologically active.
The term ‘fungicidal composition’ as used herein includes both concentrated formulations and diluted mixtures (tank-mix).
Preferred compounds of formula I are the benzoylbenzenes of formula IA,
wherein
R
1
represents a chlorine atom, a methyl, trifluoromethyl, methoxy or a hydroxy group, most preferred a methoxy group;
R
2
represents a chlorine atom or a methyl group;
R
3
represents a bromo or chloro atom, a methyl, trifluoromethyl or nitro group;
R
4
represents a methyl group;
R
5
represents an alkyl group, preferably a C
1-4
alkyl group, in particular a methyl group;
R
6
and R
7
each independently represent an alkoxy group which may be substituted by a phenyl, alkylphenyl or halophenyl group, preferably a C
1-6
alkoxy group, in particular a methoxy, ethoxy, propyloxy or butyloxy group, or a benzyl group in which the phenyl ring may be substituted by one or more halogen atoms or one or more alkyl groups; and
m is 0 or 1.
Most preferred are the following benzoylbenzenes:
6′-butoxy-2,6-dichloro-4′,5′dimethoxy-2′-methylbenzophenone (coded BB-1); 2,6-dichloro-4′,5′-dimethoxy-6′-(2′fluorobenzyloxy)-2′-methylbenzophenone (coded BB-2); 6′-benzyloxy-4′,5′-dimethoxy-2,6-dimethyl-2′-methylbenzophenone (coded BB-3); and 5-bromo-2′,6-dimethyl-2,4′,5′,6′-tetramethoxybenzophenone (coded BB-4), most preferred BB-4.
The fungicidal compositions of this invention can comprise other compounds having biological activity in addition to the benzoylbenzenes of formula I, e.g. compounds having similar or complementary fungicidal activity or compounds having plant growth regulating, herbicidal or insecticidal activity.
The other fungicidal compounds can be, for example, those which are capable of combating diseases of cereals (e.g. wheat) such as those caused by Blumeria (Erysiphe), Puccinia, Septoria, Gibberella, Botrytis and Helminthosporium spp., seed and soil borne diseases and downy and powdery mildews on vines and powdery mildew and scab on apples, Botrytis on numerous crops, leaf spot diseases on numerous crops, rice blast and rice sheath blight. These mixtures of fungicides can have a broader spectrum of activity than the compound of general formula I alone.
Examples of the other fungicidal compounds are AC 382042, alanycarb, aldimorph, ampropylfos, andoprim, anilazine, azaconazole, azafenidin, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, bialaphos, biloxazol, binapacryl, biphenyl, bitertanol, blasticidin S, Bordeaux mixture, bromuconazole, bupirimate, butenachlor, buthiobate, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chinomethionate, chlorbenzthiazon, chlorfenazol, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, copper-containing compounds such as copper oxychloride, and copper sulfate, cufraneb, cycloheximide, cymoxanil, cypofuram, cyproconazole, cyprodinil, cyprofuram, debacarb, dichlofluanid, dichlone, dichloran, dichlorophen, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, dimefluazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamin, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, ethoxyquin, etridiazole, famoxadone, fenapanil, fenamidone, fenaminosulph, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, f
Aven Michael
Cotter Henry Van Tuyl
BASF Corporation
Costello Charles F.
Killos Paul J.
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