Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2000-07-06
2001-11-06
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S134000, C504S138000, C504S286000, C504S363000
Reexamination Certificate
active
06313070
ABSTRACT:
The present invention relates to storate-stable aqueous formulations based on N-phenyl-3,4,5,6-tetrahydrophthalimide derivatives of the formula I and to their use as herbicides in crop protection
where the substituents have the following meanings:
R
1
is hydrogen, fluorine or chlorine;
R
2
is a group A—CO—B where
A is CH═C(Cl) or CH═C(Br) and
B is C
1
-C
6
-alkyl or a group OR
4
or SR
4
where
R
4
is hydrogen, C
1
-C
4
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkyloximino-C
1
-C
6
-alkyl, or
R
2
is a group OR
5
, SR
5
, COOR
5
or OCH
2
COOR
5
where
R
5
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
7
-cycloalkyl, C
3
-C
8
-alkenyl, C
3
-C
6
-alkynyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, or
R
2
is a group CH
2
—CO—OR
6
where
R
6
is C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, or a group —NHSO
2
-(C
1
-C
6
-alkyl) and
R
3
is chlorine or cyano.
Herbicides based on tetrahydrophthalimides of the formula I have been disclosed in the literature, for example in: EP-A 240 659; Herbizide, Heck, B.; Fedtke, C.; R. R. Schmidt; Thieme Stuttgart 1995, p. 144; Proc. Brighton Crop Protection Conference Weeds 1989, Vol. 1, p. 41; Proc. Brighton Crop Protection Conference Weeds 1991, Vol. 1, p. 69; Anderson et al., American Chemical Soc. Symposium Series 559 (1994), 18-33.
It can be seen from the literature that these products are formulated in most cases as solid formulations, for example water-dispersible powders or granules, or as emulsion concentrates, for example flumiclorac (trade name RESOURCE® EC, cf. The Pesticide Manual 10th Edition, p. 488) or flumioxazin (trade name SUMISOYA® WP, cf. The Pesticide Manual 10th Edition, p. 489).
The abovementioned formulations can have a series of disadvantages under practice conditions. Thus, for example, the solvents which the EC formulations (emulsion concentrate) comprise are considered as disadvantageous in the continuing debate about the environment. Moreover, the solvents used entail, as a rule, an inflammability which is not desired. In addition, the limited solubility of the active ingredients limits the preparation of highly-concentrated formulations. In the case of WP formulations (water-dispersible powders), the fact that dust is frequently generated upon use is considered to be disadvantageous.
Formulations in the form of aqueous suspension concentrates should not exhibit the disadvantages described above, but concentrates of this type were as yet unknown for tetrahydrophthalimides.
The reason for this may be the fact that the class of the tetrahydrophthalimides is described in the literature as sensitive to hydrolysis. Thus, it is known from Nippon Noyaku Gakkaishi (1989), 14(4), 497-501 (CA 1990: 215895) that tetrahydrophthalimides are not stable in aqueous systems. The half-lives of tetrahydrophthalimide measured in aqueous systems at pH 5 are 4.14 days and at pH 7 only 9.14 hours.
The lack of stability of derivatives from the class of the tetrahydrophthalimides has also been described in Biosci., Biotechnol., Biochem. (1993), 57(11) 1913-15 and Agric. Biol. Chem. (1991), 55(11), 2677-2678.
EP-A 385 231 discloses the use of certain active ingredients from the class of the tetrahydrophthalimides for the desiccation and abscission of plant organs. This publication mentions that the active ingredients can be employed in the form of various formulations, and a long list also includes highly-concentrated aqueous forms (p. 6, lines 45 et seq.). However, it can be seen from the further details that the aqueous use forms are prepared from emulsion concentrates, pastes or wettable powders, i.e. from use forms which have the disadvantages described at the outset. The starting systems always comprise solvent. EP-A 385,231 thus does not disclose storage-stable aqueous formulations to the expert, but, rather, teaches away from such a use form.
EP-A 240 659 describes certain tetrahydrophthalimides; the formulation details correspond to those in EP 385 231 which has been discussed above.
It is an object of the present invention to develop aqueous storage-stable formulations which do not have the disadvantages described at the outset. In particular, the storage stability should meet the guidelines of the FAO Manual on the development and use of FAO specifications for plant protection products, 44
th
Edition, Rome, 1992. In accordance with this manual, the product content of the formulation must not decline by more than 10% when stored at room temperature over a period of two years.
We have found that this object is achieved by aqueous suspension concentrates which comprise
a) 0.1-60% by weight of a tetrahydrophthalimide of the formula I,
b) 0.1-30% by weight of an anionic surfactant,
c) 0.1-30% by weight of a non-ionic surfactant,
d) 0.01-5% by weight of a thixotroping additive,
e) 0-50% by weight of other herbicidal active ingredients,
f) 0-20% by weight of other formulation auxiliaries, and
g) 1-90% of water.
The organic moieties mentioned in the definitions of B and R
1
to R
6
represent collective terms for individual enumerations of each of the meanings. All carbon chains, i.e. all alkyl, alkoxy, alkyloximino and alkoxyalkyl moieties, can be straight-chain or branched.
Examples of other meanings are:
C
1
-C
6
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;
(C
1
-C
6
-alkoxy)carbonyl: (C
1
-C
4
-alkoxy)carbonyl as mentioned above and, for example, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbonyl;
(C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkoxy: C
1
-C
6
-alkoxy which is substituted by (C
1
-C
6
-alkoxy)carbonyl as mentioned above, i.e. for example methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, n-butoxycarbonylmethoxy, 1-(methoxycarbonyl)ethoxy, 2-(methoxycarbonyl)ethoxy, 2-(ethoxycarbonyl)ethoxy, 2-(n-propoxycarbonyl)ethoxy, 2-(n-butoxycarbonyl)ethoxy, 3-(methoxycarbonyl)propoxy, 3-(ethoxycarbonyl)propoxy, 3-(n-propoxycarbonyl)propoxy, 3-(n-butoxycarbonyl)propoxy, 4-(methoxycarbonyl)butoxy, 4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy, 4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentoxy, 5-(ethoxycarbonyl)pentoxy, 5-(n-propoxycarbonyl)pentoxy, 5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexoxy, 6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or 6-(n-butoxycarbonyl)hexoxy, in particular methoxycarbonylmethoxy or 1-(methoxycarbonyl)ethoxy;
C
1
-C
6
-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethyl-ethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbuto
Berghaus Rainer
Bratz Matthias
Nuyken Wessel
Parg Adolf
Wigger August
BASF - Aktiengesellschaft
Clardy S. Mark
Keil Herbert B.
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