Herbicidal compositions and method of using the same

Details Herbicidal compositions and method of using the same Herbicidal compositions and method of using the same

2002-05-28

2004-04-13

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S139000, C504S206000, C504S282000

Reexamination Certificate

active

06720288

ABSTRACT:

TECHNICAL FIELD
This invention relates to a herbicidal composition having a rapid action, an improved effect and a long-term stability of preparation.
BACKGROUND ART
Among the light-induced herbicidal compositions represented by the general formula (I), the 3-substituted phenylpyrazole derivatives represented by the general formula (I-1) are known compounds disclosed in JP-A-3-163063 and JP-A-4-211065, wherein it is mentioned that these compounds have, as herbicides for foliage treatment, an outstanding herbicidal activity on the general broad-leaved weeds noxious in the upland farming.
It is known that a similar herbicidal activity is exhibited by a number of compounds resembling the general formula (I-1) in the over-all chemical structure and relative configuration of substituents used as light-induced or protox-inhibiting herbicides [Anderson et al., ACS Symposium Series, Vol. 559, Porphyric Pesticides, S. O. Duke and C. A. Robeiz eds., p.18-34 (1994)]. It is also known that a resistance to these light-induced herbicides can generally be given to plants by introducing a specific gene into the plants (International Patent Application WO98/29554).
On the other hand, organophosphorus herbicidal compounds such as the N-(phosphonomethyl)-glycine or salts thereof disclosed in JP-A-47-39538 and JP-A-57-95994, the 4-[hydroxy(methyl)phosphino]-DL-homoalanine or salts thereof disclosed in JP-A-57-26564 and the 4-[hydroxy(methyl)phosphino]-L-homoalany-L-alanyl-L-alanine or salts thereof disclosed in JP-A-50-23282, etc. are well known as non-selective herbicides for foliage treatment.
Further, JP-A-7-242510 discloses herbicidal compositions containing a 3-substituted phenylpyrazole derivative and an organophosphorus herbicidal compound.
Further, Weed Sci. Soc. 25, (1977), p.275-287 refers to the adjuvant effect of alcohol alkoxylates on N-(phosphonomethyl)glycine. However, this technique is insufficient in the adjuvant effect and the alcohol alkoxylates are not readily compatible with aqueous solution of N-(phosphonomethyl)glycine.
Thus, it has been demanded to improve the herbicidal effect and rapid action of a herbicidal composition containing a light-induced herbicidal compound (especially a 3-substituted phenylpyrazine derivative) and an organophosphorus herbicidal compound.
The present inventors have conducted extensive studies with the aim of solving the problems mentioned above to find that, by adding an ethylenediamine alkoxylate and an alcohol alkoxylate as surfactants to a herbicidal composition containing one or more compounds selected from light-induced herbicidal compounds, especially one or more compounds selected from the 3-substituted phenylpyrazole derivatives represented by the general formula (I-1), and organophosphorus herbicidal compounds as active ingredients, the rapid action of the composition can be made excellent and the effect of the composition can be improved by the synergistic action of the active ingredients and the surfactants, besides there can be obtained a herbicidal composition keeping stable for a long period of time. Based on this finding, this invention has been accomplished.
DISCLOSURE OF THE INVENTION
The present invention relates to a herbicidal composition containing one or more compounds selected from light-induced herbicidal compounds and one more compounds selected from organic herbicidal compounds as active ingredients; and containing an ethylenediamine alkoxylate and an alcohol alkoxylate as surfactants.
Particularly, the present invention relates to a herbicidal composition containing, as active ingredients, one or more compounds selected from the group consisting of the compounds represented by the following general formula (I):
wherein P represents P
1
to P
9
:
wherein X
1
, Y, Y
1
, Y
2
, R
3
, R
4
, R
5
and R
6
are as defined below, and Q represents Q
1
to Q
11
:
wherein R
1
represents a (C
1
-C
6
) alkyl group; R
2
represents a hydrogen atom, a (C
1
-C
6
) alkyl group or a halo (C
1
-C
6
) alkyl group; R
3
represents a (C
1
-C
6
) alkyl group, a halo (C
1
-C
6
) alkyl group, a (C
3
-C
6
) cycloalkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group; R
4
represents a hydrogen atom or a (C
1
-C
6
) alkyl group; R
5
represents a hydrogen atom, a (C
1
-C
6
) alkyl group, a halo (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group; R
6
represents a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group; X
1
and X
2
represent halogen atoms which may be the same or different; Y represents —O—, —S—, —SO— or —SO
2
—; Y
1
represents —O— or —S—; Y
2
represents —O—, —S— or —NH—; and n represents an integer of 0 to 1;
and more particularly, one or more compounds selected from the group consisting of the 3-substituted phenylpyrazole derivatives represented by the following general formula (I-1):
wherein R represents —Y
1
—R
3
(wherein R
3
represents a (C
1
-C
6
) alkyl group, a halo (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group; and Y
1
represents —O— or —S—), —Y
2
CH(R
4
)CO—OR
5
(wherein R
4
represents a hydrogen atom or a (C
1
-C
6
) alkyl group; R
5
represents a hydrogen atom, a (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group; and Y
2
represents —O—, —S— or —NH—), —COOCH(R
4
)CO—Y
1
R
5
(wherein R
4
, R
5
and Y
1
are as defined above), or —COOR
6
(wherein R
6
represents a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group or a (C
2
-C
6
) alkynyl group); R
1
represents a (C
1
-C
6
) alkyl group; R
2
represents a hydrogen atom, a (C
1
-C
6
) alkyl group or a halo (C
1
-C
6
) alkyl group; X
1
and X
2
represent halogen atoms which may be the same or different; Y represents —O—, —S—, —SO— or —SO
2
—; and n represents an integer of 0 to 1; and
one or more compounds selected from the group consisting of organophosphorus herbicidal compounds, and
further containing, as surfactants, an ethylenediamine alkoxylate and an alcohol alkoxylate.
MODE FOR CARRYING OUT THE INVENTION
Among the substituents in the general formula (I) and general formula (I-1), the term “(C
1
-C
6
) alkyl group” means a straight or branched chain alkyl group having 1-6 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like; “halo (C
1
-C
6
) alkyl group” means a straight or branched chain alkyl group having 1-6 carbon atoms substituted with one or more halogen atoms which are selected from the group consisting of chlorine atom, fluorine atom, iodine atom and bromine atom and may be the same or different; “(C
2
-C
6
) alkenyl group” means a straight or branched chain alkenyl group having 2-6 carbon atoms; and “(C
2
-C
6
) alkynyl group” means a straight or branched chain alkynyl group having 2-6 carbon atoms.
As examples of the light-induced herbicidal compounds of this invention, the following ones can be referred to:
(1) 3-(4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl)-5-isopropylidene-1,3-oxazolidindione (general name: pentoxazone)
(2) Pentyl [2-chloro-5-(cyclohexa-1-ene-1,2-dicarboximide)-4-fluorophenoxy]-acetate (general name: flumiclorac-pentyl)
(3) 7-Fluoro-6-[(3,4,5,6-tetrahydro)phthalimido]-4-(2-propynyl)-1,4-benzoxazin-3(2H)-one (general name: flumioxazin)
(4) Ethyl (RS)-2-chloro-3-[2-chloro-5-(4-fluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate (general name: carfentrazone-ethyl)
(5) 2′,4′-Dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-methane-sulfonanilide (general name: sulfentrazone)
(6) 2-(2,4-Dichloro-5-propyn-2-yloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one (general name: azafenidin)
(7) 5-tert-Butyl-3-[2,4-dichloro-5-(propyn-2-yloxy)phenyl]-1,3,4-oxadiazole (general name: oxadiargyl)
(8) 5-tert-Butyl-3-(2,4-dichloro-5-isopropoxy-phenyl)-1,3,4-oxadiazol-2(3H)-one (general name: oxadiazon)
(9) Me

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