Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
1999-10-11
2001-04-24
Dees, Jose′ G. (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C544S312000
Reexamination Certificate
active
06221809
ABSTRACT:
The invention relates to the technical field of crop protection agents, in particular to herbicidal compositions comprising N-[(4,6dimethoxypyrimidin-2-yl)aminocarbonyl]-5-methylsulfonamidomethyl-2-alkoxycarbonylbenzenesulfonamides and/or salts thereof.
WO 95/10507 (PCT/EP94/03369) discloses phenylsulfonylureas of the formula I and salts thereof
where the formula 1, owing to the extensive and wide definition of the radicals A, W, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
, includes a large number of possible individual compounds.
Table 1 of WO 95/10507 lists compounds of the formula 1a
the examples having the numbers 105, 209, 217, 395, 399, 403, 407, 497 and 536 relating to those compounds of the formula 1 a where Z is CH, X and Y are methoxy, R
7
is hydrogen, R
1
is alkoxycarbonyl, R
4
is hydrogen and R
5
is a radical containing a sulfonyl group (SO
2
CH
3
, SO
2
NHCH
3
, SO
2
N(CH
3
)
2
, SO
2
N(CH
3
)
2
, SO
2
CH
2
F, SO
2
CF
3
, SO
2
C
2
H5, SO
2
-n-C
3
H
7
, SO
2
CH
3
or SO
2
CH
3
). However, the melting point is only given for Examples 105 (R
1
=methoxycarbonyl, R
5
=methylsulfonyl) and 217 (R
1
=methoxycarbonyl, R
5
=SO
2
N(CH
3
)
2
) and for Example 536 (sodium salt of the compound 105).
In WO 95/10507, biological examples for the compounds mentioned individually above are given insofar as it is stated in general terms that the compounds of Examples 105, 217 and 536—in addition to a series of other compounds—have very good activity against harmful plants such as Sinapis alba, Stellaria media, Chrysanthemum segetum and Lolium multiflorum in the pre- and post-emergence method at an application rate of 0.3 kg to 0.005 kg of active substance per hectare. The crop plant safety of the compounds of the formula 1 is not documented by examples in the International Published Specification mentioned.
Furthermore, general mention is made of the possibility that the compounds of the formula 1 can be applied together with other herbicides. This mention is followed by an exemplary list of more than about 250 different standard active compounds of which, inter alia, amidosulfurone, bentazone, bifenox, bromoxynil, cafentrazon (ICI-A0051), chlortoluron, chlorsulfuron, clodinafop and its ester derivatives (for example clodinafop-propargyl), dicamba, dichlorprop, diclofop and its esters such as diclofop-methyl, difenzoquat, diflufenican, fenoxaprop and fenoxaprop-P and esters thereof such as, for example, fenoxaprop-P-ethyl and fenoxaprop-ethyl, flamprop-methyl, fluoroglycofen-ethyl, fluroxypyr, flurtamone, fomesafen, glufosinate, glyphosate, imazamethabenz-methyl, ioxynil, isoproturon, lactofen, MCPA, mecoprop, methabenzthiazuron, metribuzin, metsulfuron-methyl, pendimethalin, prosulfocarb, thifensulfuron-methyl, tralkoxydim, triasulfuron and tribenuron-methyl are explicitly mentioned. Other than just mentioning the substances, WO 95/10507 does not provide additional information with regard to the particular essence and purpose of a joint application, nor does it provide a reason for the intended selection and combination of particular active compounds.
Most phenylsulfonylureas disclosed in formula 1 and 1a of WO 95/10507 have useful to good activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants, and active compounds of the formula 1 or 1 a also allow control of weeds encountered in rice under the specific cultivation conditions such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus, Cyperus, etc., however, in many cases the individual active compounds are not sufficient to control the range of mono- and dicotyledonous weeds encountered in agricultural practice in particular in cereals or maize, but also in other crop species.
With respect to the prior art mentioned and discussed herein, it was therefore an object of the invention to provide novel mixtures having herbicidal activity to enable the expert to control, with a single application or a small number of applications of herbicides in cereals and other crop species, the range of weeds or specific weeds which are difficult to control. Furthermore, the mixtures of herbicidal active compounds which are known in principle are meant to contribute to close so-called “activity gaps” and, if possible, to reduce at the same time the application rates of the individual active compounds and to increase flexibility in the timing of the application.
This object, and other objects which have not been specifically mentioned, is achieved by herbicidal compositions having the features of in claim
1
. Thus, the invention provides herbicidal compositions, comprising
A) at least one herbicidal active compound from the group of the substituted phenylsulfonylureas of the formula I and agriculturally acceptable, i.e. safe or usable, salts thereof
in which
R
1
is (C
1
-C
8
)-alkyl, (C
3
-C
4
)-alkenyl, or (C
3
-C
4
)-alkynyl or (C
1
-C
4
)-alkyl which is mono- to tetrasubstituted by radicals selected from the group consisting of halogen and (C
1
-C
2
)-alkoxy, and
B) at least one herbicidally active compound selected from the group of the compounds consisting of
Ba) herbicides which have selective activity against grasses in cereals,
Bb) herbicides which have selective activity against dicotyledons in cereals,
Bc) herbicides which have selective activity against grasses and dicotyledons in cereals and
Bd) herbicides which are active against weed grasses and broad-leaved weeds and which are nonselective in non-crop areas or perennial crops (plantations) and/or selective in transgenic crops.
The combinations of herbicidally active compounds of types A and B according to the invention permit, in a particularly advantageous manner, the control of the range of weeds required by the expert, even including certain species which are difficult to control. In addition, using the combinations according to the invention it is possible to reduce the active compound application rates of the individual combination partners which are comprised in the combination, thus allowing more economical approaches by the user. Finally, in a not readily foreseeable way, it was possible to achieve increases in activity which surpassed expectations, the herbicidal compositions according to the invention thus showing extensive synergistic effects.
Furthermore, it was particularly surprising in the context of the invention that the sulfonylureas of the formula I carrying a methylsulfonamidomethyl substituent in position 5 of the phenyl ring in combination with other herbicides proved to be outstandingly suitable for the effective control of weed species which are difficult to control. In particular, unexpected specific activities against resistant weed grasses were observed.
Altogether, the quality of the activities found for the combinations according to the invention is generally also better than for example that found for similar combinations comprising sulfonylureas of the closest prior art, as represented for example by phenylsulfonylureas carrying iodine substituents in position 4 of the phenyl ring according to formula 2 of WO 92/13845
where the radicals according to the prior art in formula 2 are, inter alia, Q═O, R═methyl, W═O, R
1
═H, R
2
═OCH
3
, R
3
═CH
3
, Z and Y═N.
With respect to the specifically substituted phenylsulfonylureas of the formula I according to the invention it has to be stated that they are in principle embraced for example by the formula 1 of WO 95/10507, but that their outstanding suitability as combination partners for synergistic mixtures with other herbicides is not evident from the prior art. In particular, there are no indications in the known literature that the narrow and clearly defined group of the N-[(4,6dimethoxypyrimidin-2-yl)aminocarbonyl]-5methylsulfonamidomethyl-2-alkoxycarbonylbenzenesulfonamides, which may be present in the form of their salts, occupies such an exceptional position. Likewise, neither the application rates nor the ratios of the amounts of the individual compounds to be
Bieringer Hermann
Hacker Erwin
Lorenz Klaus
Dees Jose′ G.
Frommer & Lawrence & Haug LLP
Hoechst Schering AgrEvo GmbH
Pryor Alton
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