Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-10-13
2001-10-23
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S384000
Reexamination Certificate
active
06306850
ABSTRACT:
The present invention relates to novel active compound combinations which consist of the known 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
It is already known that 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione has fungicidal properties (cf. WO 96-16 048). 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 2 201 063, DE-A 2 324 0 10, Pesticide Manual, 9th Edition (1991), pages 249 and 827, U.S. Pat. No. 3,903,090 and EP-A 0 206 999). 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-imidazolidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have not hitherto been described for this compound.
It has now been found that the novel active compound combinations comprising
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione 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-(dithiocarbamate) of the formula
and/or
(6) at least one thiocarbamates 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]-decane 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 dicarboximide of the formula
and/or
(15) a pyrimidine derivative of the formula
in which
R
2
represents methyl or cyclopropyl, and/or
(16) the phenyl 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) a phenylpyrrole derivative of the formula
in which
R
3
and R
4
each represent chlorine or together represent a radical of the formula —O—CF
2
—O—, and/or
(21) the 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine of the formula
and/or
(22) the phenylurea derivative 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
5
represents hydrogen (17 to 23%) or the radical 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.
The 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula (I) is known (cf. WO 96-16 048). The compound 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 formula (II) includes the compounds
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane-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
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
It is evident from the 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 various 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-cyclopropanecarboxamide of the formula
and
N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamide 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
The formula (XXI) includes the compounds
4-(2,3-dichlorophenyl)-pyrrole-3-carbonitrile of the formula
and
4-(2,2-difluoro-1,3-benzodioxol-7-yl)-1H-pyrrole-3-carbonitrile of the formula
The guanidine derivative of the formula (XXV) is a mixture of substances of the common name guazatine.
The components which are present in the active compound combinations according to the invention in addition to the active compound of the formula (I) are also known. Specifically, the active compounds are described in the following publications:
(1) Compounds of the Formula (II)
DE-A 2 201 063
DE-A 2 324 010
(2) Compound of the Formula (III)
EP-A 0 040 345
(3) Compounds of the Formula (IV)
Pesticide Manual, 9th Edition (1991), pages 249 and 827
(4) Compound of the Formula (V) and Individual Isomers Thereof
EP-A 0 341 475
(5) Compound of the Formula (VI)
Pesticide Manual, 9th Edition (1991), page 726
(6) Compounds of the Formula (VII)
Pesticide Manual, 9th Edition (1991), pages 529, 531 and 866
(7) Compound of the Formula (VIII)
EP-A 0 339 418
(8) Compound of the Formula (IX)
EP-A 0 472 996
(9) Compound of the Formula (X)
EP-A 0 313 512
(10) Compound of the Formula (XI)
EP-A 0 281 842
(11) Compound of the Formula (XII)
EP-A 0 382 375
(12) Compound of the Formula (XIII)
EP-A 0 515 901
(13) Compound of the Formula (XIV)
EP-A 196 02 095
(14) Compound of the Formula (XV)
U.S. Pat. No. 3,903,090
(15) Compounds of the Formula (XVI)
EP-A 0 270 111
EP-A 0 310 550
(16) Compound of the Formula (XVII)
Pesticide Manual, 9th Edition (1991), page 159
(17) Compound of the Formula (XVIII)
EP-A 0 219 756
(18) Compound of the Formula (XIX)
Pesticide Manual, 9th Edition (1991), page 431
(19) Compound of the Formula (XX)
Pesticide Manual, 9th Edition (1991), page 443
(20) Compounds of the Formula (XXI)
EP-A 0 236 272
EP-A 0 206 999
(21) Compound of the Formula (XXII)
Pesticide Manual, 9th Edition (1991), page 491
(22) Compound of the Formula (XXIII)
DE-A 2 732 257
(23) Compound of the Formula (XXIV)
EP-A 0 600 629
(24) Substance of the Formula (XXV)
Pesticide Manual, 9th Edition (1991), page 461
In addition to the active compound of the Formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (24). Additionally, they may comprise further fungicidally active components.
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (1),
0.1
Dutzmann Stefan
Jautelat Manfred
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Robinson Allen J.
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