Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
1999-07-14
2002-12-10
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S132000, C504S133000, C504S134000, C504S135000
Reexamination Certificate
active
06492301
ABSTRACT:
The invention relates to the technical field of crop protection agents and relates in particular to herbicidal compositions comprising compounds of the formula I
in which
R
1
is (C
1
-C
8
)-alkyl, (C
3
-C
4
)-alkenyl, (C
3
-C
4
)-alkynyl or (C
1
-C
4
)-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C
1
-C
2
)-alkoxy;
R
1
is I, or CH
2
NHSO
2
CH
3
;
R
3
is methyl or methoxy; and
Z is N or CH;
and/or their salts, which are highly suitable for controlling weeds in rice which have hitherto been difficult to control with individual herbicides, in particular grass-like, dicotyledonous and/or cyperaceae-like weeds in rice or transgenic crops of rice.
For the relevant prior art, the following publications may be mentioned:
WO 92/13845 (PCT/EP92/00304) =D1,
WO 95/10507 (PCT/EP94/03369)=D2,
WO 96/41537 (PCT/EP96/02443)=D3 and
WO 98/24320 (PCT/EP97/06416)=D4.
D1 discloses iodinated arylsulfonylureas of the formula I and salts thereof,
where the formula I embraces a large number of possible individual compounds, owing to the extensive and broad definition of the radicals Q, W, Y, Z, R, R
1
, R
2
and R
3
.
D1 indicates, in a general manner, that the compounds of the formula I may be used together with other herbicides. This indication is followed by an exemplary enumeration of more than about 250 different standard active compounds. Information about a particular reason and purpose of joint application is, except for the fact that the substances are mentioned, not given in D1, nor a motivation for targetted selection and combination of certian active compounds.
D2 discloses phenylsulfonylureas of the formula 2 and salts thereof
where, once more, the formula 2 embraces a very large number of possible individual compounds, owing to the extensive and broad definition of the radicals A, W, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
.
In Table 1 of D2, compounds of the formula (2a) are listed
where the examples Nos. 105, 209, 217, 395, 399, 403, 407, 497 and 536 relate to those compounds of the formula 2a in which Z is CH, X and Y is methoxy, R
7
is hydrogen, R
1
is alkoxycarbonyl, R
4
is hydrogen and R
5
is a radical which contains 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
, preferably SO
2
CH
3
).
D2 gives biological examples for the compounds mentioned individually above in that, in a general manner, it is mentioned that the compounds of Examples 105, 217 and 536—in addition to a large number of other compounds—have very good activity against harmful plants such as Sinapis alba, Stellaria media, Chrysanthemum segetum and Lolium multiflorum when applied pre- or post-emergence at an application rate of from 0.3 kg to 0.005 kg of active substance per hectare. In the abovementioned international laid-open publication, the crop plant compatibility of the compounds of the formula 2 or 2a is not demonstrated by any examples.
Furthermore, D2 indicates, in a general manner, the possibility of using the compounds of the formula 2 together with other herbicides. This indication is followed by an exemplary list of more than about 250 different standard active compounds. The proposed combinations seem to have been given more or less at random, and they do not teach anything that exceeds the fact that herbicides can be combined in principle.
D3 discloses herbicidal compositions comprising
A) at least one herbicidally active compound from the group of the substituted phenylsulfonylureas of the formula 3
in which
R
1
is (C
1
-C
8
)-alkyl, (C
3
-C
4
)-alkenyl, (C
3
-C
4
)-alkynyl or (C
1
-C
4
)-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C
1
-C
2
)-alkoxy
and
B) at least one herbicidally active compound from the group of the compounds consisting of
Ba) herbicides that are selective in cereals and/or in maize against grasses,
Bb) herbicides that are selective in cereals and/or maize against dicotyledonous plants,
Bc) herbicides that are selective in cereals and/or maize against grasses and dicotyledonous plants and
Bd) herbicides that are nonselective in non-crop land and/or selective in transgenic crops against wheat-grasses and broad-leaved weeds.
D3 discloses, in particular, combinations of the sulfonylurea of the formula 3 with fenoxaprop, fenoxaprop-P, isoproturon, diclofop, clodinafop, mixtures of clodinafop and cloquintocet, chlortoluron, methabenzthiazuron, imazamethabenz, tralkoxydim, difenzoquat, flamprop, flamprop-M, pendimethalin, nicosulfuron, rimsulfuron, primisulfuron, mecoprop, mecoprop-P, MCPA, dichlorprop, dichlorprop-P, 2,4-D, dicamba, fluroxypyr, ioxynil, bromoxynil, bifenox, fluoroglycofen, acifluorfen, lactofen, fomesafen, oxyfluorfen, ET-751, azoles according to WO/08999, diflufenican, bentazon, metolachlor, metribuzin, atrazin, terbuthylazin, alachlor, acetochlor, dimethenamid, amidosulfuron, metsulfuron, tribenuron, thifensulfuron, triasulfuron, chlorsulfuron, prosulfuron or CGA-152005, sulfonylureas according to WO 94/10154, flupyrsulfuron (DPX-KE459), sulfosulfuron (MON37500), KIH-2023, glufosinate, glufosinate-P or glyphosate.
The particular combinations that are mentioned are synergistic, the area of use is limited to cereals and maize.
D4 discloses combinations comprising:
A) at least one compound from the group of the substituted phenylsulfonylureas of the formula 4 and their agriculturally accepted salts
in which
R
1
is (C
1
-C
8
)-alkyl, (C
3
-C
4
)-alkenyl, (C
3
-C
4
)-alkynyl or (C
1
-C
4
)-alkyl, which is mono- to tetrasubstituted by radicals from the group consisting of halogen and (C
1
-C
2
)-alkoxy
and
B) at least one herbicidally active compound from the group of the compounds consisting of
Ba) herbicides which are selective in cereals against grasses,
Bb) herbicides which are selective in cereals against dicotyledonous plants,
Bc) herbicides which are selective in cereals against grasses and dicotyledonous plants and
Bd) herbicides which are nonselective in non-crop land or in perennial crops (plantations) and/or selective in transgenic crops against wheat grasses and broad-leaved weeds.
In particular, combinations with fenoxaprop, fenoxaprop-P, isoproturon, diclofop, clodinafop, mixtures of clodinafop and cloquintocet, chlortoluron, methabenzthiazuron, imazamethabenz, tralkoxydim, difenzoquat, flamprop, flamprop-M, pendimethalin, mecoprop, mecoprop-P, MCPA, dichlorprop, dichlorprop-P, 2,4-D, dicamba, fluroxypyr, ioxynil, bromoxynil, bifenox, fluoroglycofen, lactofen, fomesafen, oxyfluorfen, ET-751, azoles according to WO 94/08999, F 8426, diflufenican, bentazon, metribuzin, metosulam, flupoxam, prosulfocarb, flurtamone, amidosulfuron, metsulfuron, tribenuron, thifensulfuron, triasulfuron, chlorsulfuron, sulfonylureas according to WO 94/10154, sulfonylureas according to WO 92/13845, flupyrsulfuron (DPX-KE459), MON 48500, sulfosulfuron (MON37500), glufosinate, glufosinate-P or glyphosate are known.
Most of the sulfonylureas known from D1 and D2 according to the formulae 1 and 2 have useful to good activity against a broad spectrum of mono- and dicotyledonous harmful plants of economic importance, and even weeds which are encountered under the specific cultivation conditions in rice, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus, Cyperus etc., are controlled with the aid of active compounds of the formulae 1, 2 and 3; however, for optimum control of the spectrum of mono- and dicotyledonuos weeds encountered in agricultural practice especially in rice, the individual active compounds are frequently insufficient. Moreover, the synergistic combinations of D3 or D4 can generally not be used with above-average success in rice. At least, this could not be expected with a more than average probability, in particular because the useful plant rice is, to a not unconsiderable extent, damaged by most of the combinations known from D3 or D4, so that these are not suitable for use in crop s of rice.
Moreover, there exist, i
Bieringer Hermann
Hacker Erwin
Clardy S. Mark
Frommer & Lawrence & Haug LLP
Hoechst Schering AgrEvo GmbH
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