Fungicidal active compound combinations

Details Fungicidal active compound combinations Fungicidal active compound combinations

2000-04-03

2001-06-12

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...

C514S478000, C514S479000

Reexamination Certificate

active

06245772

ABSTRACT:

The present application relates to new active compound combinations composed of, on the one hand, valinamide derivatives and, on the other hand, of other, known fungicidal active compounds, and which are highly suitable for combating phytopathogenic fungi.
It is already known that valinamide derivatives has fungicidal properties (cf. EP-A 472,996). The activity of this substance is good; however, it leaves something to be desired in some cases when low application rates are used.
Furthermore, it is already known that a large number of azole derivatives, aromatic carboxylic acid derivatives, morpholine compounds and other heterocycles can be employed for combating fungi (cf. K. H. Büchel “Pflanzenschutz und Schädlingsbekämpfung” [Crop Protection and Pest Control] pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag, Stuttgart 1977). However, the activity of the substances in question is not always satisfactory when low application rates are used.
It has now been found that the new active compound combinations of valinamide derivatives of the general formula (I)
in which
R
1
represents i-propyl or s-butyl and
R
2
represents chlorine, methyl, ethyl or methoxy,
and
(A) dichlofluanid, of the formula
and/or
(B) tolyifluanid, of the formula
and/or
(C) tetrachloro-isophthalo-nitrile of the formula
and/or
(D) propineb, of the formula
and/or
(E) tetramethyl-thiuram-disulphide, of the formula
and/or
(F) mancozeb, of the formula
and/or
(G) dyrene, of the formula
and/or
(H) copper oxychloride
and/or
(I) captan of the formula
and/or
(K) a morpholine derivative of the formula
and/or
(L) dithianon, of the formula
and/or
(M) Phaltan, of the formula
and/or
(N) cymoxanil, of the formula
and/or
(O) propamocarb, of the formula
(CH
3
)
2
NCH
2
—CH
2
—CH
2
—NHCO—OCH
2
CH
3
  (XIII)
or its hydrochloride
and/or
(P) fosetyl, of the formula
or the aluminium adduct thereof
and/or
(Q) metalaxyl, of the formula
and/or
(R) oxadixyl, of the formula
and/or
(S) fluazinam, of the formula
and/or
(T) methoxyacrylates, such as methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate, of the formula
and/or
(U) methoximinoacetates, such as methyl (E)-methoximino[&agr;-(o-tolyloxy)-o-tolyl]acetate of the formula
and/or
(V) furalaxyl
&Lgr;
methyl-N- (2-furoyl) -N- (2,6-xylyl) -alanit
and/or
(W) azoles of the formula
I X=Cl, Y=—(CH(OH)—(Triadimenol)
III X=Cl, Y=—CO—(triadimefon)
IV tebuconazole of the formula
and/or
(X) etridiazole=3-trichlormethyl-5-ethoxy-1,2,4-thiadiazole
and/or
(Y) pencycuron=1-(4-chlorbenzyl)-1-cyclopentyl-(3-phenylurea have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is substantially greater than the total of the activities of the individual active compounds. This means that a true synergistic effect, which could not have been predicted, is present, not merely a complemented activity.
It can be seen from the structural formula of the active compounds of the formula (I) that the compounds have two asymmetrically substituted carbon atoms. The product can therefore exist in the form of mixture of various isomers or else in the form of a single isomer.
Preferred compounds of the formula (I) are compounds in which the amino acid moiety is formed by ipropyloxycarbonyl-L-valine or sec-butoxycarbonyl-L-valine and the phenethylamine moiety is either racemic or has the S(−) configuration, but in particular the R(+) configuration
Particularly preferred compounds of the formula (I) are the compounds in which R
1
represents i-propyl.
Particular mention may be made of the compounds 1-methylethyl [2-methyl-1-[[[-1-(4-chlorophenyl)ethyl]-amino]carbonyl]-carbamate, of the formula (II)
1-Methylethyl [2-methyl-1-[[[1-(4-methylphenyl)ethyl]-amino]carbonyl]-propyl]-carbamate, of the formula (III)
1-Methylethyl [2-methyl-1-[[[-1-(4-ethylphenyl)ethyl]-amino]carbonyl]-propyl]-carbamate, of the formula (IV)
and 1-methylethyl [2-methyl-1-[[[-1- (4-methoxyphenyl)ethyl]amino]carbonyl]-propyl]-carbamate, of the formula
and their isomers, as mentioned above.
The active compounds of the formula (I) are known (cf. EP-A 472,996).


REFERENCES:
patent: 5453531 (1995-09-01), Seitz et al.
patent: 472996 (1991-08-01), None
patent: 493683 (1991-11-01), None
patent: 550788 (1992-01-01), None
Brighton Crop Protection Conference (1992) 5-6, 435-37.

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