CA1334249C - Herbicidal composition - Google Patents
Herbicidal compositionInfo
- Publication number
- CA1334249C CA1334249C CA000605103A CA605103A CA1334249C CA 1334249 C CA1334249 C CA 1334249C CA 000605103 A CA000605103 A CA 000605103A CA 605103 A CA605103 A CA 605103A CA 1334249 C CA1334249 C CA 1334249C
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- CA
- Canada
- Prior art keywords
- parts
- glyphosate
- compound
- composition
- herbicidal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Abstract
The present invention is directed to a herbicidal composition which comprises as the active ingredients (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) N-(phosphonomethyl)-glycine or a salt thereof (glyphosate), and an inert carrier or diluent. The composition exerts a synergistic herbicidal activity.
Description
HERBICIDAL COMPOSITION
The present invention relates to a herbicidal composition. More particularly, it relates to a herbicidal composition comprising as the active ingredients (a) 2-~7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl}-4,5,6,7-tetrahydro-lH-isoindole-1,3(2H)-dione (here-inafter referred to as "Compound (I)") of the formula:
O
~N~ ( I) and (b) N-(phosphonomethyl)glycine of the formula:-HO
HO~ 2 2 (II) or a salt LI~L (hereinafter referred to as "gl~osaLen), which exerts a highly enhanced herbicidal activity against a wide variety of weeds.
In recent years, there have been used a great number of chemicals having herbicidal activities in order to exter~;n~te or control undesirable weed vege~ation in~
agricultural and non-agricultural fields. Since, however, there are a diverse variety of weeds which exhibit gr~ over a long period of time, the herbicidal effects of conventional herbicidal agents are generally restricted. Under the circumstances, the appearance of a herbicidal agent exerting a strong 2 l 334249 herbicidal activity as well as a broad herbicidal spectrum over a wide variety of weeds would be highly desirable.
Glyphosate is known as a herbicide applicable before planting or plowing, but it takes a relatively long time to completely exterminate the undesired weeds after its application, e.g. about 10 days or more. If this period can be shortened, it would be a great advantage for r~ as ~ubse~h~L tasks, e.g. pl~nt;n~ and plowing, can be performed sooner after ~rl;~;on of the herbicide.
As a result of the extensive study, it has now been found that the associated use of Compound (I) with glyphosate as active ingredients produces a highly enhanced herbicidal activity against a wide variety of weeds in agricultural and non-agricultural fields. In comparison with the sole use of each of said active insredients, enh~ncement of the herbicidal potency on such associated use is remarkable so that the active ingredients may be applied in smaller dosages. Further, the weed-control spectrum is greatly enlarged. Furthermore, in comparison with the sole use of glyphosate, the herbicidal effect is exerted much quickly, e.g. within one or two days after the applica-tion. Accordingly, the complete exterminaton of the weeds, though it varies depending on the species, is realized almost within one week. Thus, a clear and definite synergistic effect is observed in said associated use.
The herbicidal composition of the invention can exterminate or control a variety of weeds, of which typical examples are broad-leaved weeds~ e.g. wild `_ 1 334249 buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), common purslane (Portulaca oleracea), common chickweed (Stellaria media), common lambsquarters (Chenopodium album), redroot pigweed (Amaranthus retroflexus), slender amaranth (Amaranthus gracilis), radish (Raphanus sativus), wild mustard (Sinapis arvensis), shepherdspurse (Capsella bursa-pastoris), hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa), field pansy (Viola arvensis), catchweed bedstraw - (Galium aparine), ivyleaf mornin'gglory (Ipomoea hederacea), tall morningglory (Pharbitis purpurea), field bindweed (Convolvulus arvensis), flexuous bittercress (Car~m;ne flexuosa), prickly sow-thistle (Sonchus asper), fleabane (Erigeron sumatrensis), purple deadnettle (Lamium purpureum), henbit (Lamium amplexicaure), jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), persian speedwell (Veronica persica), common cocklebur (Xanthium ' strumarium), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata), corn marigold (Chrysanthemum segetum), curly dock (Rumex crispus) and Japanese mugwort (Artemisia princeps); graminaceous weeds, e.g. japanese millet (~chinochloa frumentacea), barn-yardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), water foxtail (Alopecurus geniculatus), large crabgrass (Digitaria sanguinalis), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), oats (Avena sativa), wild oats (Avena fatua), johnsongrass (Sorqhum ~ 1 334249 halepense), quackgrass (Agropyron repens), downy brome (Brcmus tectorum), bluestem (Agropyron tsukushiense) and bermudagrass (Cynodon dactylon); commelinaceous weeds, e.g. AC;~;C dayflcwer (Commelina co~ n; S); cyperaceous weeds, e.g. rice flatsedge (Cyperus iria) and purple nutsedge (Cyperus rotundus), etc.
Compound (I) is known to exert a herbicidal activity (U.S. patent 4,640,707). Glyphosate is described in C.R. Worthing et al: The Pesticide Manual , 8th Ed., page 449 (1987) published by The British Crop Protection Council, and it can be used as such or in an agriculturally acceptable salt form (e.g. isopropylamine salt). However, the associated use of Compound (I) with glyphosate has never been attempted, and the productlon of synergism on the associated use has never been expected.
The proportion of Compound (I) as the component (a) and glyphosate as the component (b) in the composition of the invention may vary over a considerably broad range and is usually within a range of 1 : 0.5 to 1 : 100 by weight, preferably of 1 : 1 to 1 : 70 by weight, more preferably of 1 : 2.5 to 1 : 40 by weight.
In addition to the active ingredients as above, the composition may contain a solid or liquid carrier or diluent. Surface active or auxiliary agents may be also contained therein. Thus, the compositon may be formulated in any conventional preparation form, e.g. wettable powder or suspension. The total content of the active ingredients, i.e. Compound (I) and glyphosate, may be from 1 to 90 % by -weight, preferably from 2 to 80 % by weight.
As the solid carrier or diluent, there may be used kaolin clay, attapulgite clay, bentonite, terra alba, pyro-phyllite, talc, diatomaceous earth, calcite, walnut-shell 5 powder, urea, ammonium sulfate, synthetic hydrated silica, etc. Examples of the liquid carrier or diluent are water, etc.
The surface active agent used for dispersion or spreading may be any of the anionic and non-ionic type of agents. Examples of the surface active agent include alkylsulfates, alkylarylsulfonates, dialkylsulfosuccinates, phosphates of polyoxyethylenealkylaryl ethers, polyoxy-ethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. Examples of the auxiliary agents include ligninsulfonates, sodium alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP ~isopropyl acid phosphate), etc.
Practical embodiments of the composition are illustratively shown in the following Formulation Examples wherein part(s) are by weight.
Formulation Example 1 One part of Compound (I), 50 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 44 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
- ~ 1 334249 Formulation Example 2 One part of Compound (I), 20 parts of glyphosate, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 73 parts of water are mixed and pulverized until the particle size is less than 5 microns to make a sus-pension.
Formulation Example 3 Twenty-five parts of Compound (I), 25 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 4 0.7 Parts of Compound (I), 49 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45.3 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 5 1.5 Parts of Compound (I), 50 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 43.5 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 6 0.4 Parts of Compound (I), 1.6 parts of glyphosate, 1 part of polyoxyethylene sorbitan monooleate, 1 part of CMC
and 96 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to make a sus-pension.
Formulation ~ P 7 0.4 Parts of Compound (I), 10 parts of "Sorpol 5050"~ (an anionic surface active agen. manufactured by Toho Yakuhin Kogyo K.K.; containing 50 % dialkylsulfosuccinate), 4 parts of sodium ligninsulfonate, 5 parts of synthetic hydrated silica and 79 ~s of clay are mixed well. 1.6 Parts of glyphosate are added thereto, and the mixture is pulve-rized well to obtain a wettable powder.
A composition comprising Compound (I) and glyphosate thus formulated is useful for post-emergence control of undesired weeds by foliar treatment, etc. The foliar treatment may be effected by spraying the composition cont~;n;ng Compound (I) and glyphosate over the top of the plants. Direct application methods may also be adopted.
In order to improve the herbicidal activity, the composition may be used with other herbicides. It may also be used in combination with insecticides, acaricides, nematocides, fungicides, plant growth regulators, ferti-lizers, soil improvers, etc.
The composition of the invention is widely used as a herbicide applicable to plowed fi~lds, non-cropping land, orchards, pasture land,laWns, forests, non-agricultural fields, etc.
The dosage of the active ingredients may vary depending on prevailing weather conditions, soil involved, formulation used, mixing proportion of each active in-gredient, crop and weed species, etc. In general, however, the total amount of Compound (I) and glyphosate may be within a range of about 100 to 5000 grams per hectare, ` 1 334249 preferably within a range of about 200 to 3000 grams per hectare.
The composition in the form of a wettable powder, suspension or the like is normally diluted with water and applied at a volume of 100 to 1000 liters per hectare to the area where the extermination of the weeds is desired. The dilution may further include, in addition to the above mentioned surface active agent, spreading or auxiliary agents, e.g. polyoxyethylene resin acid esters, lignin-sulfonates, abietic acid, dinaphthylmethanedisulfonates, paraffin or petroleum oil.
The herbicidal activity of the composition of the invention will be explained in further detail with reference to the following Test Examples. Further, throughout the Test Examples, glyphosate was used in the form of an isopropyl-amine salt.
Test Example 1 Sandy upland field soil was filled in concrete pots (50 x 50 x 30 cm), and seeds of downy brome, wild oats, water foxtail, catchweed bedstraw, wild buckwheat and flexuous bittercress were sown therein and cultivated outdoors for 40 days. A spe~;f;e~ amount of the composition in the form of a wettable powder formulated according to Formulation Example 1, 3, 4 or 5 was diluted with water contAin;~g a 0.2 % (v/v) surfactant (contA;n;ng dialkyl-sulfosuccinate) and sprayed to the foliage of the test plants at a spray volume of 500 liters per hectare with the aid of a small hand sprayer. At three and n;n~tepn days thereafter, the herbicidal activity was observed. The results are shown in Tables 1 and 2 wherein the herbicidal activity was observed visually and classified numerically ranging from O (no control) to 10 (complete death). At the time of treatment, the weeds were at the 1 to 3~ f stage and 4 to 8 cm in height.
Table 1 Test Dosage tIerbicidal activity 3 days after treatment Compound(g/ha) Downy Wild Water Catchweed Wild Flexuous brome oats fox- bedstraw buck- bitter-tail wheat cress Compound (I)lO 2.5 4 3.5 8 8.5 8 4 3.5 6 8.5 9 9 100 5 5.5 7 9 9 - 9 1100 7 8.5 9 9 10 9 Glyphosate500 2 2.5 3 1.5 2.5 3 1000 4 5 4 4 4.5 5 2000 4 5 4.5 4 4.5 5.5 Compound (I)10 + 500 9 9.5 9 9 9.5 9.5 r~
Glyphosate10 + 1000 9.5 10 9.5 9 10 10 '9 30 + 500 9 10 10 9.5 9.5 10 30 + 1000 9.5 10 10 9.5 10 10 100 + 500 9.5 10 10 9.5 9.5 10 100 + 1000 9.5 10 10 10 10 10 Table 2 Test Dosage Herbicidal activity l9 days after treatment Compound (g/ha) Downy Wild Water Catchweed Wild Flexuous brome oats fox- bedstraw buck- bitter-tail wheat cress Compound (I) lO 3 4 4 9 10 9.5 4.5 4 6 9.5 lO lO
lO0 6 5.5 ~ 9.8 10 lO
1100 7 9.5 9.8 lO 10 10 Glyphosate 500 6 6 7 0.5 1.5 5 lO00 9 9.3 9 5.5 5.5 8 2000 10 lO 9.8 8 ~.8 9.3 Compound (I)10 + 500 9.5 lO lO 9 lO lO
GlyphosatelO + lO00 9.8 lO lO 9.8 lO 10 30 + 500 9.8 lO lO lO lO lO
30 + 1000 lO 10 lO lO lO lO
lO0 + 500 lO lO lO lO lO lO
100 + 1000 10 10 10 10 10 10 Test Example 2 Pear fields where large crabgrass, barnyardgrass, prickly sow-thistle, fleabane, ladysthumb and slender amaranth spontaneously germinated were plotted with three replicates (each plot being 2.8 x 3.6 m). A spe~;f;e~ amount of the composition in the form of a wettable powder formu-lated according to Formulation Example 1, 3, 4 or 5 was diluted with water cont~;n;ng a 0.2 % (v/v) surfactant (cont~in;ng dialkylsulfosuccinate) and sprayed to the foliage of the test plants at a spray volume of 1000 liters per hectare with the aid of a small hand sprayer. Sixteen days thereafter, the herbididal activity was observed. At the time of treatment, large crabgrass, barnyardgrass, prickly sow-thistle, fleabane, ladysthum and slender amaranth were in 5 to 10, 30 to 40, 30 to 40, 5 to 10, 40 to 70 and 5 to 10 cm in height, respectively. The results are shown in Table 3 wherein the herbicidal activity was evaluated according to the same manner as in Test Example 1.
Table 3 Test Dosage Herbicidal activity Compound (~/ha) Large Barn- Prickly Fleabane Ladys- Slender crab- yard- sow-thistle thumamaranth grass brass Compound (I) 30 4.3 3.7 6 4 8.77.3 7 5.3 9 6.3 9 9 860 9 7 10 9.7 9.710 Glyphosate 800 8.3 8 7 7 4 7 1200 9 9 8 7.7 6 10 Compound (I)30 + 800 9.3 97 10 9.7 10 10 Glyphosate 60 + 800 10 10 10 10 10 10 - 14 - l 3 3 4 2 4 9 .
Test Example 3 Sandy upland field soil was filled in Wagner pots (inner diameter, 16 cm; height, 19 cm), and seeds of downy brome were sown therein and cultivated outdoors for 40 days. A .spe~;fie~ amount of the composition in the form of a wettable powder formulated according to Formulation Example 1, 3, 4 or 5 was diluted with water contA; n ing a 0.2 % (v/v) surfactant (contA;n;ng 80 % polyoxyethylene dodecyl ether) and sprayed to the foliage of the test plant at a spray volume of 500 liters per hectare with the aid of a small hand sprayer. Twenty days thereafter, growth control percentage was observed, and the results are shown in Table 4. At the time of treatment, the test plant was at 3-leaf stage and 10 cm in height. The growth control percentage (%) was determined by weighing the aerial parts of the test plants (fresh weight) and making a c~ Ation A~c~r~;ng to `
the following equation:
Growth Fresh weight of test controlling _ ~l plant in treated plot x lO0 percentage Fresh weight of test (%) ~ plant in untreated plot Table 4 G~ound (I) (g/ha) Glypho- 0 0 7 13 25 49 66 84 99 sate 100 20 33 40 52 75 82 (g/ha)200 44 60 83 87 92 96 The results in Test Example 3 were analyzed according to the isobole (i.e. equivalent efficacy line) method [Vol. 3, Herbicides, pages 109 - 111 (1981) in "Noyaku Jikkenho" (Methods in Pesticide Science) edited by Junichi Fukami et al., Soft Science Inc., Tokyo) based on the Tammes's method [Tammes, P.M.L.: Neth. J. Plant Path., 70, 73-80 (1964)]. Namely, several combinations of the compositions having different mixing ratios of Compound (I) and glyphosate but exerting the same level of growth control effect, for example, 90 % growth control, were plotted on a graph so as to readily determine a synergistic effect, an arithmetic effect or a competitive effect. In the case of exhibiting the synergistic effect, the equivalent efficacy line as plotted is shown below the arithmetic efficacy line.
Expl~ining further in detail with reference to the accompanying drawings, Fig. 1 wherein the ordinate indicates the dosage of glyphosate and the abscissa indicates the dosage of Compound (I), the equivalent efficacy line (i.e.
' solid line) of 90 % growth control of downy brome is located under the arithmetic efficacy line (i.e. dotted line), from which it is understood that the associated use of Compound (I) and glyphosate in certain mixing ratios produces the synergistic effect.
The present invention relates to a herbicidal composition. More particularly, it relates to a herbicidal composition comprising as the active ingredients (a) 2-~7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl}-4,5,6,7-tetrahydro-lH-isoindole-1,3(2H)-dione (here-inafter referred to as "Compound (I)") of the formula:
O
~N~ ( I) and (b) N-(phosphonomethyl)glycine of the formula:-HO
HO~ 2 2 (II) or a salt LI~L (hereinafter referred to as "gl~osaLen), which exerts a highly enhanced herbicidal activity against a wide variety of weeds.
In recent years, there have been used a great number of chemicals having herbicidal activities in order to exter~;n~te or control undesirable weed vege~ation in~
agricultural and non-agricultural fields. Since, however, there are a diverse variety of weeds which exhibit gr~ over a long period of time, the herbicidal effects of conventional herbicidal agents are generally restricted. Under the circumstances, the appearance of a herbicidal agent exerting a strong 2 l 334249 herbicidal activity as well as a broad herbicidal spectrum over a wide variety of weeds would be highly desirable.
Glyphosate is known as a herbicide applicable before planting or plowing, but it takes a relatively long time to completely exterminate the undesired weeds after its application, e.g. about 10 days or more. If this period can be shortened, it would be a great advantage for r~ as ~ubse~h~L tasks, e.g. pl~nt;n~ and plowing, can be performed sooner after ~rl;~;on of the herbicide.
As a result of the extensive study, it has now been found that the associated use of Compound (I) with glyphosate as active ingredients produces a highly enhanced herbicidal activity against a wide variety of weeds in agricultural and non-agricultural fields. In comparison with the sole use of each of said active insredients, enh~ncement of the herbicidal potency on such associated use is remarkable so that the active ingredients may be applied in smaller dosages. Further, the weed-control spectrum is greatly enlarged. Furthermore, in comparison with the sole use of glyphosate, the herbicidal effect is exerted much quickly, e.g. within one or two days after the applica-tion. Accordingly, the complete exterminaton of the weeds, though it varies depending on the species, is realized almost within one week. Thus, a clear and definite synergistic effect is observed in said associated use.
The herbicidal composition of the invention can exterminate or control a variety of weeds, of which typical examples are broad-leaved weeds~ e.g. wild `_ 1 334249 buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), common purslane (Portulaca oleracea), common chickweed (Stellaria media), common lambsquarters (Chenopodium album), redroot pigweed (Amaranthus retroflexus), slender amaranth (Amaranthus gracilis), radish (Raphanus sativus), wild mustard (Sinapis arvensis), shepherdspurse (Capsella bursa-pastoris), hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa), field pansy (Viola arvensis), catchweed bedstraw - (Galium aparine), ivyleaf mornin'gglory (Ipomoea hederacea), tall morningglory (Pharbitis purpurea), field bindweed (Convolvulus arvensis), flexuous bittercress (Car~m;ne flexuosa), prickly sow-thistle (Sonchus asper), fleabane (Erigeron sumatrensis), purple deadnettle (Lamium purpureum), henbit (Lamium amplexicaure), jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), persian speedwell (Veronica persica), common cocklebur (Xanthium ' strumarium), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata), corn marigold (Chrysanthemum segetum), curly dock (Rumex crispus) and Japanese mugwort (Artemisia princeps); graminaceous weeds, e.g. japanese millet (~chinochloa frumentacea), barn-yardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), water foxtail (Alopecurus geniculatus), large crabgrass (Digitaria sanguinalis), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), oats (Avena sativa), wild oats (Avena fatua), johnsongrass (Sorqhum ~ 1 334249 halepense), quackgrass (Agropyron repens), downy brome (Brcmus tectorum), bluestem (Agropyron tsukushiense) and bermudagrass (Cynodon dactylon); commelinaceous weeds, e.g. AC;~;C dayflcwer (Commelina co~ n; S); cyperaceous weeds, e.g. rice flatsedge (Cyperus iria) and purple nutsedge (Cyperus rotundus), etc.
Compound (I) is known to exert a herbicidal activity (U.S. patent 4,640,707). Glyphosate is described in C.R. Worthing et al: The Pesticide Manual , 8th Ed., page 449 (1987) published by The British Crop Protection Council, and it can be used as such or in an agriculturally acceptable salt form (e.g. isopropylamine salt). However, the associated use of Compound (I) with glyphosate has never been attempted, and the productlon of synergism on the associated use has never been expected.
The proportion of Compound (I) as the component (a) and glyphosate as the component (b) in the composition of the invention may vary over a considerably broad range and is usually within a range of 1 : 0.5 to 1 : 100 by weight, preferably of 1 : 1 to 1 : 70 by weight, more preferably of 1 : 2.5 to 1 : 40 by weight.
In addition to the active ingredients as above, the composition may contain a solid or liquid carrier or diluent. Surface active or auxiliary agents may be also contained therein. Thus, the compositon may be formulated in any conventional preparation form, e.g. wettable powder or suspension. The total content of the active ingredients, i.e. Compound (I) and glyphosate, may be from 1 to 90 % by -weight, preferably from 2 to 80 % by weight.
As the solid carrier or diluent, there may be used kaolin clay, attapulgite clay, bentonite, terra alba, pyro-phyllite, talc, diatomaceous earth, calcite, walnut-shell 5 powder, urea, ammonium sulfate, synthetic hydrated silica, etc. Examples of the liquid carrier or diluent are water, etc.
The surface active agent used for dispersion or spreading may be any of the anionic and non-ionic type of agents. Examples of the surface active agent include alkylsulfates, alkylarylsulfonates, dialkylsulfosuccinates, phosphates of polyoxyethylenealkylaryl ethers, polyoxy-ethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. Examples of the auxiliary agents include ligninsulfonates, sodium alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP ~isopropyl acid phosphate), etc.
Practical embodiments of the composition are illustratively shown in the following Formulation Examples wherein part(s) are by weight.
Formulation Example 1 One part of Compound (I), 50 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 44 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
- ~ 1 334249 Formulation Example 2 One part of Compound (I), 20 parts of glyphosate, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 73 parts of water are mixed and pulverized until the particle size is less than 5 microns to make a sus-pension.
Formulation Example 3 Twenty-five parts of Compound (I), 25 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 4 0.7 Parts of Compound (I), 49 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45.3 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 5 1.5 Parts of Compound (I), 50 parts of glyphosate, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 43.5 parts of synthetic hydrated silica are mixed well and pulverized to obtain a wettable powder.
Formulation Example 6 0.4 Parts of Compound (I), 1.6 parts of glyphosate, 1 part of polyoxyethylene sorbitan monooleate, 1 part of CMC
and 96 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to make a sus-pension.
Formulation ~ P 7 0.4 Parts of Compound (I), 10 parts of "Sorpol 5050"~ (an anionic surface active agen. manufactured by Toho Yakuhin Kogyo K.K.; containing 50 % dialkylsulfosuccinate), 4 parts of sodium ligninsulfonate, 5 parts of synthetic hydrated silica and 79 ~s of clay are mixed well. 1.6 Parts of glyphosate are added thereto, and the mixture is pulve-rized well to obtain a wettable powder.
A composition comprising Compound (I) and glyphosate thus formulated is useful for post-emergence control of undesired weeds by foliar treatment, etc. The foliar treatment may be effected by spraying the composition cont~;n;ng Compound (I) and glyphosate over the top of the plants. Direct application methods may also be adopted.
In order to improve the herbicidal activity, the composition may be used with other herbicides. It may also be used in combination with insecticides, acaricides, nematocides, fungicides, plant growth regulators, ferti-lizers, soil improvers, etc.
The composition of the invention is widely used as a herbicide applicable to plowed fi~lds, non-cropping land, orchards, pasture land,laWns, forests, non-agricultural fields, etc.
The dosage of the active ingredients may vary depending on prevailing weather conditions, soil involved, formulation used, mixing proportion of each active in-gredient, crop and weed species, etc. In general, however, the total amount of Compound (I) and glyphosate may be within a range of about 100 to 5000 grams per hectare, ` 1 334249 preferably within a range of about 200 to 3000 grams per hectare.
The composition in the form of a wettable powder, suspension or the like is normally diluted with water and applied at a volume of 100 to 1000 liters per hectare to the area where the extermination of the weeds is desired. The dilution may further include, in addition to the above mentioned surface active agent, spreading or auxiliary agents, e.g. polyoxyethylene resin acid esters, lignin-sulfonates, abietic acid, dinaphthylmethanedisulfonates, paraffin or petroleum oil.
The herbicidal activity of the composition of the invention will be explained in further detail with reference to the following Test Examples. Further, throughout the Test Examples, glyphosate was used in the form of an isopropyl-amine salt.
Test Example 1 Sandy upland field soil was filled in concrete pots (50 x 50 x 30 cm), and seeds of downy brome, wild oats, water foxtail, catchweed bedstraw, wild buckwheat and flexuous bittercress were sown therein and cultivated outdoors for 40 days. A spe~;f;e~ amount of the composition in the form of a wettable powder formulated according to Formulation Example 1, 3, 4 or 5 was diluted with water contAin;~g a 0.2 % (v/v) surfactant (contA;n;ng dialkyl-sulfosuccinate) and sprayed to the foliage of the test plants at a spray volume of 500 liters per hectare with the aid of a small hand sprayer. At three and n;n~tepn days thereafter, the herbicidal activity was observed. The results are shown in Tables 1 and 2 wherein the herbicidal activity was observed visually and classified numerically ranging from O (no control) to 10 (complete death). At the time of treatment, the weeds were at the 1 to 3~ f stage and 4 to 8 cm in height.
Table 1 Test Dosage tIerbicidal activity 3 days after treatment Compound(g/ha) Downy Wild Water Catchweed Wild Flexuous brome oats fox- bedstraw buck- bitter-tail wheat cress Compound (I)lO 2.5 4 3.5 8 8.5 8 4 3.5 6 8.5 9 9 100 5 5.5 7 9 9 - 9 1100 7 8.5 9 9 10 9 Glyphosate500 2 2.5 3 1.5 2.5 3 1000 4 5 4 4 4.5 5 2000 4 5 4.5 4 4.5 5.5 Compound (I)10 + 500 9 9.5 9 9 9.5 9.5 r~
Glyphosate10 + 1000 9.5 10 9.5 9 10 10 '9 30 + 500 9 10 10 9.5 9.5 10 30 + 1000 9.5 10 10 9.5 10 10 100 + 500 9.5 10 10 9.5 9.5 10 100 + 1000 9.5 10 10 10 10 10 Table 2 Test Dosage Herbicidal activity l9 days after treatment Compound (g/ha) Downy Wild Water Catchweed Wild Flexuous brome oats fox- bedstraw buck- bitter-tail wheat cress Compound (I) lO 3 4 4 9 10 9.5 4.5 4 6 9.5 lO lO
lO0 6 5.5 ~ 9.8 10 lO
1100 7 9.5 9.8 lO 10 10 Glyphosate 500 6 6 7 0.5 1.5 5 lO00 9 9.3 9 5.5 5.5 8 2000 10 lO 9.8 8 ~.8 9.3 Compound (I)10 + 500 9.5 lO lO 9 lO lO
GlyphosatelO + lO00 9.8 lO lO 9.8 lO 10 30 + 500 9.8 lO lO lO lO lO
30 + 1000 lO 10 lO lO lO lO
lO0 + 500 lO lO lO lO lO lO
100 + 1000 10 10 10 10 10 10 Test Example 2 Pear fields where large crabgrass, barnyardgrass, prickly sow-thistle, fleabane, ladysthumb and slender amaranth spontaneously germinated were plotted with three replicates (each plot being 2.8 x 3.6 m). A spe~;f;e~ amount of the composition in the form of a wettable powder formu-lated according to Formulation Example 1, 3, 4 or 5 was diluted with water cont~;n;ng a 0.2 % (v/v) surfactant (cont~in;ng dialkylsulfosuccinate) and sprayed to the foliage of the test plants at a spray volume of 1000 liters per hectare with the aid of a small hand sprayer. Sixteen days thereafter, the herbididal activity was observed. At the time of treatment, large crabgrass, barnyardgrass, prickly sow-thistle, fleabane, ladysthum and slender amaranth were in 5 to 10, 30 to 40, 30 to 40, 5 to 10, 40 to 70 and 5 to 10 cm in height, respectively. The results are shown in Table 3 wherein the herbicidal activity was evaluated according to the same manner as in Test Example 1.
Table 3 Test Dosage Herbicidal activity Compound (~/ha) Large Barn- Prickly Fleabane Ladys- Slender crab- yard- sow-thistle thumamaranth grass brass Compound (I) 30 4.3 3.7 6 4 8.77.3 7 5.3 9 6.3 9 9 860 9 7 10 9.7 9.710 Glyphosate 800 8.3 8 7 7 4 7 1200 9 9 8 7.7 6 10 Compound (I)30 + 800 9.3 97 10 9.7 10 10 Glyphosate 60 + 800 10 10 10 10 10 10 - 14 - l 3 3 4 2 4 9 .
Test Example 3 Sandy upland field soil was filled in Wagner pots (inner diameter, 16 cm; height, 19 cm), and seeds of downy brome were sown therein and cultivated outdoors for 40 days. A .spe~;fie~ amount of the composition in the form of a wettable powder formulated according to Formulation Example 1, 3, 4 or 5 was diluted with water contA; n ing a 0.2 % (v/v) surfactant (contA;n;ng 80 % polyoxyethylene dodecyl ether) and sprayed to the foliage of the test plant at a spray volume of 500 liters per hectare with the aid of a small hand sprayer. Twenty days thereafter, growth control percentage was observed, and the results are shown in Table 4. At the time of treatment, the test plant was at 3-leaf stage and 10 cm in height. The growth control percentage (%) was determined by weighing the aerial parts of the test plants (fresh weight) and making a c~ Ation A~c~r~;ng to `
the following equation:
Growth Fresh weight of test controlling _ ~l plant in treated plot x lO0 percentage Fresh weight of test (%) ~ plant in untreated plot Table 4 G~ound (I) (g/ha) Glypho- 0 0 7 13 25 49 66 84 99 sate 100 20 33 40 52 75 82 (g/ha)200 44 60 83 87 92 96 The results in Test Example 3 were analyzed according to the isobole (i.e. equivalent efficacy line) method [Vol. 3, Herbicides, pages 109 - 111 (1981) in "Noyaku Jikkenho" (Methods in Pesticide Science) edited by Junichi Fukami et al., Soft Science Inc., Tokyo) based on the Tammes's method [Tammes, P.M.L.: Neth. J. Plant Path., 70, 73-80 (1964)]. Namely, several combinations of the compositions having different mixing ratios of Compound (I) and glyphosate but exerting the same level of growth control effect, for example, 90 % growth control, were plotted on a graph so as to readily determine a synergistic effect, an arithmetic effect or a competitive effect. In the case of exhibiting the synergistic effect, the equivalent efficacy line as plotted is shown below the arithmetic efficacy line.
Expl~ining further in detail with reference to the accompanying drawings, Fig. 1 wherein the ordinate indicates the dosage of glyphosate and the abscissa indicates the dosage of Compound (I), the equivalent efficacy line (i.e.
' solid line) of 90 % growth control of downy brome is located under the arithmetic efficacy line (i.e. dotted line), from which it is understood that the associated use of Compound (I) and glyphosate in certain mixing ratios produces the synergistic effect.
Claims (6)
1. A herbicidal composition which comprises as the active ingredients (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) N-(phosphonomethyl)glycine or a salt thereof (glyphosphate), and an inert carrier or diluent wherein the weight proportion of the components (a) and (b) is from 1:0.5 to 1:100.
2. The composition according to claim 1, wherein the weight proportion of the components (a) and (b) is from 1:1 to 1:70.
3. A method for controlling weeds which comprises applying a herbicidally effective amount of the composition according to claim 1 to the weeds.
4. The method according to claim 3, wherein the total amount of the components (a) and (b) is from 100 to 5000 grams per hectare.
5. The method according to claim 3, wherein the total amount of the components (a) and (b) is from 200 to 3000 grams per hectare.
6. A process for preparing a herbicidal composition which comprises mixing (a) 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and (b) N-(phosphonomethyl)glycine or a salt thereof (glyphosphate), with an inert carrier or diluent, wherein the weight proportion of the components (a) and (b) is from 1:0.5 to 1:100.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63171346A JP2606300B2 (en) | 1988-07-08 | 1988-07-08 | Herbicidal composition |
| JP171346/1988 | 1988-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1334249C true CA1334249C (en) | 1995-02-07 |
Family
ID=15921506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000605103A Expired - Lifetime CA1334249C (en) | 1988-07-08 | 1989-07-07 | Herbicidal composition |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4994102A (en) |
| EP (1) | EP0354346B1 (en) |
| JP (1) | JP2606300B2 (en) |
| AU (1) | AU607627B2 (en) |
| BR (1) | BR8903354A (en) |
| CA (1) | CA1334249C (en) |
| DE (1) | DE68903902T2 (en) |
| ES (1) | ES2053879T3 (en) |
| MY (1) | MY104039A (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2662053B1 (en) * | 1990-05-21 | 1992-08-07 | Rhone Poulenc Agrochimie | HERBICIDE SOLUTIONS BASED ON N-PHOSPHONOMETHYLGLYCIN. |
| TW202380B (en) * | 1991-10-16 | 1993-03-21 | Sumitomo Chemical Co | |
| WO1994018836A1 (en) * | 1993-02-17 | 1994-09-01 | Schering Aktiengesellschaft | Synergistic herbicidal composition on the basis of thidiazimin |
| JP5433120B2 (en) * | 1999-09-30 | 2014-03-05 | モンサント テクノロジー エルエルシー | Packaged mix pesticide composition with improved stability |
| AU774112B2 (en) | 2000-03-14 | 2004-06-17 | Sumitomo Chemical Company, Limited | Aqueous pesticidal composition |
| US20050101488A1 (en) * | 2003-10-21 | 2005-05-12 | Sumitomo Chemical Company, Limited | Herbicidal composition |
| TW201433263A (en) * | 2005-07-04 | 2014-09-01 | Sumitomo Chemical Co | Method for producing pesticidal composition and method for controlling weeds |
| BRPI0722192A2 (en) * | 2007-10-30 | 2014-06-24 | Sumitomo Chemical Co | HERBICIDE COMPOSITION. |
| US7939466B2 (en) * | 2008-03-26 | 2011-05-10 | Ricks Phillip E | Method of crop production |
| US20100005689A1 (en) * | 2008-07-10 | 2010-01-14 | Cqms Pty Ltd | Heavy duty excavator bucket |
| US10422103B2 (en) * | 2008-07-10 | 2019-09-24 | Cqms Pty Ltd | Heavy duty excavator bucket |
| EP2858506B1 (en) * | 2012-06-06 | 2020-07-22 | Dow AgroSciences LLC | High strength herbicidal suspension concentrates |
| US20150173363A1 (en) * | 2013-12-24 | 2015-06-25 | Sumitomo Chemical Company, Limited | Weed control composition |
| US9545109B2 (en) | 2014-08-28 | 2017-01-17 | Sumitomo Chemical Company, Limited | Herbicidal composition |
| US9545108B2 (en) * | 2014-08-28 | 2017-01-17 | Sumitomo Chemical Company, Limited | Herbicidal composition |
| CN108782597B (en) * | 2017-04-26 | 2021-08-06 | 四川利尔作物科学有限公司 | Suspending agent containing glyphosate and flumioxazin |
| US10555528B1 (en) | 2019-03-20 | 2020-02-11 | Sumitomo Chemical Company, Limited | Herbicidal composition and method for controlling weeds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
| US3929450A (en) * | 1974-06-28 | 1975-12-30 | Monsanto Co | Herbicidal compositions and methods |
| HU182980B (en) * | 1979-12-28 | 1984-03-28 | Nitrokemia Ipartelepek | Concentrates and spray solutions containing n-bracket-phosphono-methyl-bracket closed-glycine |
| US4612034A (en) * | 1982-12-27 | 1986-09-16 | J. T. Baker Chemical Company | Herbicidal formulation |
| US4640707A (en) * | 1984-07-23 | 1987-02-03 | Sumitomo Chemical Company, Ltd. | Tetrahydrophthalimides and their herbicidal use |
-
1988
- 1988-07-08 JP JP63171346A patent/JP2606300B2/en not_active Expired - Lifetime
-
1989
- 1989-06-20 MY MYPI89000830A patent/MY104039A/en unknown
- 1989-07-03 US US07/374,867 patent/US4994102A/en not_active Expired - Lifetime
- 1989-07-04 ES ES89112199T patent/ES2053879T3/en not_active Expired - Lifetime
- 1989-07-04 DE DE8989112199T patent/DE68903902T2/en not_active Expired - Lifetime
- 1989-07-04 EP EP89112199A patent/EP0354346B1/en not_active Expired
- 1989-07-05 AU AU37863/89A patent/AU607627B2/en not_active Expired
- 1989-07-07 CA CA000605103A patent/CA1334249C/en not_active Expired - Lifetime
- 1989-07-07 BR BR898903354A patent/BR8903354A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE68903902T2 (en) | 1993-04-22 |
| EP0354346A1 (en) | 1990-02-14 |
| BR8903354A (en) | 1990-02-13 |
| ES2053879T3 (en) | 1994-08-01 |
| US4994102A (en) | 1991-02-19 |
| JPH0222209A (en) | 1990-01-25 |
| DE68903902D1 (en) | 1993-01-28 |
| AU607627B2 (en) | 1991-03-07 |
| MY104039A (en) | 1993-10-30 |
| EP0354346B1 (en) | 1992-12-16 |
| AU3786389A (en) | 1990-01-11 |
| JP2606300B2 (en) | 1997-04-30 |
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