Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2000-10-13
2002-09-17
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
Reexamination Certificate
active
06451733
ABSTRACT:
BACKGROUND OF THE INVENTION
Aryloxypicolinamides such as those described in U.S. Pat. No. 5,294,597 demonstrate excellent herbicidal activity, in particular against broadleaf weeds in cereal crops. However, said aryloxypicolinamides, when used as the sole active ingredient, do not always achieve effective control of the full spectrum of weed species encountered in commercial agronomic practice at application rates required for acceptable crop safety. Such gaps in the spectrum of control can often be remedied by co-treatment with another herbicide known to be effective against the relevant weed species. It has been disclosed (U.S. Pat. No. 5,674,807) that selected combinations of aryloxypicolinamides produce not merely the expected additive effect, but may exhibit a significant synergistic effect (i.e., the combination shows a much higher level of activity than that which could be predicted from that of the individual components). This synergistic effect enables a greater margin of safety for the crop species. However, the disclosure is limited to two-way combinations of aryloxypicolinamides and members of selected known chemical classes which do not include herbicidal partners in the imidazolinone, cyclohexanedione, aryloxyphenoxy-propionic acid, or pyridinecarboxylic acid classes. Moreover, although the phenoxyacetic acid chemical class is disclosed, 2,4-dichlorophenoxyacetic acid (2,4-D) is not specifically exemplified.
Therefore it is an object of this invention to provide synergistic, crop-selective herbicidal combinations with broad-spectrum weed control.
It is another object of this invention to provide herbicidal compositions useful for the synergistic control of a broad-spectrum of weeds in the presence of a crop.
SUMMARY OF THE INVENTION
Although aryloxypicolinamide compounds demonstrate excellent herbicidal activity, when applied alone they do not always achieve the desired spectrum of weed control at rates required for acceptable crop safety. Surprisingly, it has now been found that a two-way combination comprising an aryloxypicolinamide compound of formula I
wherein
Z represents an oxygen or sulfur atom;
R
1
represents a hydrogen or halogen atom or an alkyl or haloalkyl group;
R
2
represents a hydrogen or an alkyl group;
q is 0 or 1;
R
3
represents a hydrogen or an alkyl or alkenyl group;
the or each group X independently represents a halogen atom or an optionally substituted alkyl or alkoxy group, preferably a haloalkyl group, or an alkenyloxy, cyano, carboxy, alkoxycarbonyl, (alkylthio)carbonyl, alkylcarbonyl, amido, alkylamido, nitro, alkylthio, haloalkylthio, alkenylthio, alkynylthio, alkylsulphinyl, alkylsulphonyl, alkyloxyminoalkyl or alkenyloximinoalkyl group;
n is 0 or an integer from 1 to 5;
the or each group Y independently represents a halogen atom or an alkyl, nitro, cyano, haloalkyl, alkoxy or haloalkoxy group; and
m is 0 or an integer from 1 to 5 plus a second herbicide selected from 2,4-dichlorophenoxyacetic acid (2,4-D), an imidazolinone, a cyclohexanedione, an aryloxyphenoxypropionic acid, or a pyridinecarboxylic acid herbicide demonstrates a synergistic herbicidal effect. Further, unexpectedly, a selected three-way combination comprising an aryloxypicolinamide compound of formula I and 2,4-D and a third herbicide selected from the group consisting of an imidazolinone, a cyclohexanedione, and an aryloxyphenoxypropionic acid herbicide produces a significant synergistic effect. Advantageously, the synergistic two-way and three-way combinations of the invention allow for lower application rates of said aryloxypicolinamide with concomittant increased spectrum of weed control. Moreover, the synergistic herbicidal methods and compositions of the invention allow for effective resistance management.
The present invention provides a method for the synergistic control of undesirable plants such as Polygonum, Kochia, Galeopsis, Galium, Stelaria, Sinapis, and Avena which comprises applying to the locus of said plants or to the foliage or stems of said plants a synergistically effective amount of a two-way combination comprising an aryloxypicolinamide compound of formula I plus a second herbicide selected from 2,4-D, an imidazolinone, a cyclohexanedione, an aryloxyphenoxypropionic acid, or a pyridinecarboxylic acid herbicide. The present invention also provides a method for the synergistic control of undesirable plants which comprises applying to the locus of said plants a synergistically effective amount of a three-way combination comprising an aryloxypicolinamide compound of formula I, 2,4-D, and a third herbicide selected from the group consisting of an imidazolinone, a cyclohexanedione, or an aryloxyphenoxypropionate herbicide.
The present invention also provides a synergistic herbicidal composition which comprises an agriculturally acceptable carrier and a synergistically effective amount of a two-way combination of an aryloxypicolinamide compound of formula I plus a second herbicide selected from 2,4-D, an imidazolinone, a cyclohexanedione, an aryloxyphenoxypropionic acid, or a pyridinecarboxylic acid herbicide; or a three-way combination of an aryloxypicolinamide compound of formula I, 2,4-D, and a third herbicide selected from the group consisting of an imidazolinone, a cyclohexanedione, and an aryloxyphenoxypropionate herbicide.
DETAILED DESCRIPTION OF THE INVENTION
Aryloxypicolinamides of formula I
wherein Z, R
1
, R
2
, R
3
, X, n, Y and m are defined herein above and methods for their preparation are described in U.S. Pat. No. 5,294,597. Said aryloxypicolinamides demonstrate excellent herbicidal activity, in particular against broadleaf weeds in cereal crops. However, said aryloxypicolinamides when used as the sole active ingredient do not always achieve effective control of the full spectrum of weed species encountered in commercial agronomic practice, in conjunction with reliable selectivity for the crop species.
Surprisingly, it has now been found that a two-way combination of an aryloxypicolinamide of formula I and a second herbicide selected from 2,4-D, an imidazolinone, a cyclohexanedione, an aryloxyphenoxypropionic acid, or a pyridinecarboxylic acid herbicide provides synergistic control of troublesome weeds such as Polygonum, Kochia, Galeopsis, Galium, Stelaria, Sinapis, and Avena. Also, surprisingly, a three-way combination of an aryloxypicolinamide of formula I and 2,4-D plus a third herbicidal compound selected from the group consisting of an imidazolinone, a cyclohexanedione, and an aryloxyphenoxypropionic acid herbicide provides synergistic weed control. That is, the application of the two-way or three-way combinations of the invention gives a mutual reinforcing action such that the application rates of the individual herbicidal components can be reduced and still the same herbicidal effect is achieved or, alternatively, the application of the combination of herbicidal components demonstrates a greater herbicidal effect than expected from the effect of the application of the individual herbicidal components when applied singly at the rate at which they are present in the combination (synergistic effect).
In the specification and claims, the term 2,4-D designates 2,4-dichlorophoxyacetic acid. Examples of an imidazolinone herbicide suitable for use in the methods and compositions of the invention include imazapyr, imazethapyr, imazapic, imazaquin, imazamox, imazamethabenz methyl, or the like, preferably imazamethabenz methyl.
A cyclohexanedione herbicide suitable for use in the methods and compositions of the invention include sethoxydim, clethodim, alloxydim, tralkoxydim, cycloxydim, or the like, preferably tralkoxydim.
Exemplary of aryloxyphenoxypropionate herbicides suitable for use in the inventive methods and compositions are diclofop methyl, fluazifop-p-butyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, quizalofop-p-terfuryl, quizalofop-p, haloxyfop-methyl, clodinafop-propargyl, isoxapurifop, cyhalofop butyl, fenthioprop, propaquizafop, or the like, preferably fenoxaprop-p-ethyl.
A pyridinecarboxylic acid herbicide such as picloran,
Killins Roy Allan
Pidskalny Ronald Steven
BASF - Aktiengesellschaft
Clardy S. Mark
Keil & Weinkauf
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