Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-06-07
2003-09-23
Pryor, Alton N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S229500, C514S256000, C514S359000
Reexamination Certificate
active
06624183
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel active compound combinations which consist of a known fluoro-benzothiazole derivative and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
BACKGROUND OF THE INVENTION
It is already known that isopropyl 1-({[1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-amino}carbonyl)-2-methylpropylcarbamate has fungicidal properties (cf. EP-A1-775 696). The activity of this compound is good; however, at low application rates it is in some cases not satisfactory.
Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be employed for controlling fungi (cf. EP-A 0 040 345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9th Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). Likewise, the activity of these compounds is not always satisfactory at low application rates.
Finally, it is also known that 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazo-lidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have hitherto not been described for this compound.
Furthermore, it is already known that 1-(3,5-dimethyl-isoxazol-4-sulphonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5f]-benzimidazole has fungicidal properties (cf. WO 97-06171).
Furthermore, it is already known that substituted azodioxacycloalkenes have fungicidal properties (cf. EP-B-712 396).
Finally, it is also known that substituted halogenopyrimidines have fungicidal properties (cf. DE-A1-196 46 407, EP-B-712 396).
DETAILED DESCRIPTION OF THE INVENTION
It has now been found that the novel active compound combinations comprising a fluorobenzothiazole derivative of the formula
and
(1) a triazole derivative of the formula
in which
X represents chlorine or phenyl and
Y represents
and/or
(2) the triazole derivative of the formula
and/or
(3) an aniline derivative of the formula
in which
R
1
represents hydrogen or methyl,
and/or
(4) N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula
and/or
(5) the zinc propylene-1,2-bis-(dithiocarbamidate) of the formula
and/or
(6) at least one thiocarbamate of the formula
Me=Zn or Mn or a mixture of Zn and Mn
and/or
(7) the aniline derivative of the formula
and/or
(8) the compound of the formula
and/or
(9) the benzothiadiazole derivative of the formula
and/or
(10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro [5,4]-de-cane of the formula
and/or
(11) the compound of the formula
and/or
(12) the compound of the formula
and/or
(13) the compound of the formula
and/or
(14) the cyanoxime derivative of the formula
and/or
(15) a pyrimidine derivative of the formula
in which
R
2
represents methyl, —C≡C—CH
3
(mepanipyrim) or cyclopropyl (cyprodinyl),
and/or
(16) an aniline derivative of the formula
and/or
(17) the morpholine derivative of the formula
and/or
(18) the phthalimide derivative of the formula
and/or
(19) the phosphorus compound of the formula
and/or
(20) the hydroxyethyl-triazole derivative of the formula
and/or
(21) the 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula
and/or
(22) the oxazolidinedione of the formula
and/or
(23) the benzamide derivative of the formula
and/or
(24) a guanidine derivative of the formula
in which
m represents integers from 0 to 5 and
R
3
represents hydrogen (17 to 23%) or the radical of the formula
and/or
(25) the triazole derivative of the formula
and/or
(26) the halogeno-benzimidazole of the formula
and/or
(27) the halogenopyrimidine of the formula
and/or
(28) the tetrachloro-isophthalo-dinitrile of the formula
and/or
(29) the compound of the formula
and/or
(30) the pyridineamine of the formula
and/or
(31) the thiazolecarboxamide of the formula
and/or
(32) the sulphonamide of the formula
and/or
(33) the compound of the formula
and/or
(34) the compound of the formula
and/or
(35) the compound of the formula
and/or
(36) the diamide of the formula
and/or
(37) the methoxyacrylate derivative of the formula
and/or
(38) the quinoline derivative of the formula
and/or
(39) the phenylamide derivative of the formula
and/or
(40) the phenylamide derivative of the formula
and/or
(41) the dicarboxime derivative of the formula
and/or
(42) the phosphonic acid of the formula
and/or
(43) the pyrrole derivative of the formula
and/or
(44) the phenyl carbonate of the formula
and/or
(45) the copper compounds
a) copper oxychloride (XXXXVIa)
b) copper hydroxid (XXXXVIb)
and/or
(46) the imidazole derivative of the formula
and/or
(47) the triazole derivative of the formula
(48) a compound of the general formula
R
1
represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl,
and/or
(49) N-methyl-2-(methoxyimino)-2-[2-([1-(3-tri-fluoro-methylphenyl)ethoxy]iminomethyl)phenyl]acetamide of the formula
and/or
(50) 2,4-dihydro-5-methoxy-2-methyl-4-[2-([([1-(3-tri-fluoro-methylphenyl)ethylidene]amino)oxy]methyl)phenyl]-3H-1,2,4-triazol-3-one of the formula
and/or
(51) the compound of the formula
have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable, true synergistic effect is present, and not just an addition of activities.
From the structural formula of the active compound of the formula (I), it can be seen that the compound has two asymmetrically substituted carbon atoms. Accordingly, the product can be present as a mixture of different 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 from i-propyloxycarbonyl-L-valine and the fluoro-benzothiazoleethylamine moiety is racemic, but has, in particular, the (R) configuration.
The formula (II) includes the compounds
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
and
1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
The formula (IV) includes the aniline derivatives of the formulae
and
It is evident from the structural formula for the active compound of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds
N—(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopro-panecarboxamide of the formula
and
N—(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopro-panecarboxamide of the formula
The formula (VII) includes the compounds
(VIIa)
Me = Zn
(zineb),
(VIIb)
Me = Mn
(maneb) and
(VIIc)
mixture of (VIIa) and (VIIb)(mancozeb).
The formula (XVI) includes the compounds
(XVIa)
R
2
= CH
3
(pyrimethanil) and
(XVIb)
(cyprodinyl)
(XVIc)
R
2
= —C≡C—CH
3
(mepanipyrim)
The compound of the formula (XVII) can be present as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate (metalaxyl, XVIIa) or as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (metalaxyl-M, XVIIb).
The hydroxyethyl-triazole derivative of the formula (XXI) can be present in the “thiono” form of the formula
or in the tautomeric “mercapto” form of the formula
For simplicity's sake, only the “thiono” form is given in each case.
The guanidine derivative of the formula (XXV) is a substance mixture with the common name guazatine.
From the s
Assmann Lutz
Gayer Herbert
Heinemann Ulrich
Krämer Wolfgang
Krüger Bernd-Wieland
Bayer Aktiengesellschaft
Henderson Richard E. L.
Mrozinski, Jr. John E.
Pryor Alton N.
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