Herbicidal composition

Information

  • Patent Application
  • 20070254810
  • Publication Number
    20070254810
  • Date Filed
    April 19, 2007
    17 years ago
  • Date Published
    November 01, 2007
    17 years ago
Abstract
A herbicidal composition which comprises N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl)cyclohex-1-ene-1,2-dicarboxamide (flumioxazin) and a compound represented by the formula (I):
Description
EXAMPLES

Hereinafter, the present invention is explained by examples in detail.


Formulation examples are given below. In the following examples, part(s) means part(s) by weight.


Formulation Example 1

Twenty-five parts of flumioxazin, 25 parts of Compound [I], 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45 parts of synthetic hydrated silica are well pulverized and mixed to give wettable powder.


Formulation Example 2

Seventy parts of flumioxazin, 14 parts of Compound [I], 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 11 parts of synthetic hydrated silica are well pulverized and mixed to give wettable powder.


Formulation Example 3

Fourteen parts of flumioxazin, 70 parts of Compound [I], 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 11 parts of synthetic hydrated silica are well pulverized and mixed to give wettable powder.


Formulation Example 4

Ten parts of flumioxazin, 5 parts of Compound [I], 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 80 parts of synthetic hydrated silica are well pulverized and mixed to give wettable powder.


Formulation Example 5

Twenty parts of flumioxazin, 20 parts of Compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 54 parts of water are mixed and wet-pulverized to make the particle diameter to 5μ or less to give suspensible concentrate.


Formulation Example 6

Fifty parts of flumioxazin, 10 parts of Compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 34 parts of water are mixed and wet-pulverized to make the particle diameter to 5μ or less to give suspensible concentrate.


Formulation Example 7

Five parts of flumioxazin, 25 parts of Compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 64 parts of water are mixed and wet-pulverized to make the particle diameter to 5μ or less to give suspensible concentrate.


Formulation Example 8

Four parts of flumioxazin, 2 parts of Compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 88 parts of water are mixed and wet-pulverized to make the particle diameter to 5μ or less to give suspensible concentrate.


Formulation Example 9

One part of flumioxazin, one part of Compound [I], 0.5 part of Neocol YSK (sodium dialkylsulfosuccinate ester produced by Dai-ichi Kogyo Seiyaku Co., Ltd.), 2 parts of Toxanon GR31A (anionic polycarboxylate surfactant produced by Sanyo Chemical Industries, Ltd.), 30 parts of Kunigel V1 (bentonite produced by Kuminime Industries Co., Ltd.) and 65.5 parts of calcium carbonate are charged into a small kneader, mixed, kneaded, granulated with an extruder (RG-5M manufactured by Kikusui Seisakusho, Ltd.) and dried with a fluidized bed dryer (MDB-400 manufactured by Fuji Paudal Co., Ltd.), and then filtered with 16-48 mesh to give granules.


Biological test is given below.


Valuation Basis

The herbicidal activity is evaluated at 11 levels using the indices of 0 to 10, i.e., shown by 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, wherein a score of “0” means that there is no or little difference in the degree of growth between treated plants and untreated plants at the time of observation and a score of “10” means that the test plants die completely or their growth is completely inhibited. The herbicidal values of “7”, “8”, “9” and “10” show excellent herbicidal activity, and the value “6” or less shows insufficient herbicidal activity. The phytotoxicity against crops is evaluated by using “no damage”, “small”, “medium” or “severe”, wherein “no damage” means that no or little damage is found, “small” means that the damage is light, “medium” means that the damage is medium and “severe” means that severe damage is found.


Test Example 1

Plastic pots each having a diameter of 18 cm and a height of 14 cm were filled with upland soil, and then seeded with wheat and barnyardgrass. On the surface of the soil of the above-mentioned plastic pots, Flumioxazin granules (granules containing 0.25% of flumioxazin, commercial name: Broad Star, produced by Valent U.S.A.), granules containing Compound [I] (prepared by using one part of Compound [I], 0.5 part of Neocol YSK, 2 parts of Toxanon GR31A, 30 parts of Kunigel VI and 66.5 parts of calcium carbonate according to Formulation example 9), and a mixture of the Flumioxazin granules with the granules containing Compound [I] were applied with hand in a designated amount given by Table 1.


The treated plants were grown in the greenhouse. The herbicidal activity and phytotoxicity against the crop were examined 48 days after the application. The results are shown in Table 1.












TABLE 1







Herbicidal
Phytotoxicity



Amount of active
activity
against crop


Test compound
ingredient (g/ha)
Barnyardgrass
Wheat







flumioxazin
40
4
No damage


Compound [I]
50
0
No damage



100 
2
No damage


flumioxazin +
40 + 50 
7
No damage


Compound [I]
40 + 100
10 
No damage









As shown in Test example 1, excellent herbicidal effect was synergistically provided in the area treated with the composition of the invention compared to the area treated with flumioxazin or Compound [I] solely. Further, there was no damage found in wheat.


Test Example 2

Plastic pots each having a diameter of 9 cm and a height of 7 cm were filled with upland soil, and then seeded with peanut. Next day, a mixture of Flumioxazin WDG (water dispersible granules containing 51% of flumioxazin, commercial name: Valor SX, produced by Valent U.S.A.) and emulsifiable concentrate containing Compound [I] (prepared by dissolving Compound [I] with acetone containing Tween 20 (surfactant, sorbitan monolaurate polyglycol ether)) was diluted with a designated amount of water, and applied uniformly on the surface of the soil with a small sprayer.


The treated plants were grown in the greenhouse. The herbicidal activity and phytotoxicity against the crop were examined 21 days after the application. The results are shown in Table 2.













TABLE 2









Phytotoxicity




Amount of active
against crop



Test compound
ingredient (g/ha)
Peanut









flumioxazin + Compound [I]
25 + 50
No damage




50 + 50
No damage




100 + 100
No damage










As shown in Test example 2, the composition of the invention caused no or little damage against peanut.


Test Example 3

Plastic pots each having a width of 32 cm, a depth of 22 cm and a height of 8 cm were filled with upland soil, and then planted with a tuber of yellow nutsedge. Next day, Flumioxazin WDG (water dispersible granules containing 51% of flumioxazin, commercial name: Valor SX, produced by Valent U.S.A.), emulsifiable concentrate containing Compound [I] (prepared by dissolving Compound [I] with acetone containing Tween 20 (surfactant, sorbitan monolaurate polyglycol ether)) and a mixture thereof was diluted with a designated amount of water, and applied uniformly on the surface of the soil with a small sprayer.


The treated plants were grown in the greenhouse. The herbicidal activity and phytotoxicity against the crop were examined 21 days after the application. The results are shown in Table 3.











TABLE 3






Amount of active
Herbicidal activity


Test compound
ingredient (g/ha)
Yellow nutsedge

















flumioxazin
25
0



50
1


Compound [I]
100 
7


flumioxazin + Compound [I]
25 + 100
9



50 + 100
10









As shown in Test example 3, excellent herbicidal effect was synergistically provided in the area treated with the composition of the invention compared to the area treated with flumioxazin or Compound [I] solely.


Test Example 4

Plastic pots each having a width of 32 cm, a depth of 22 cm and a height of 8 cm were filled with upland soil, and then transplanted with tomato and seeded with crabgrass and redroot pigweed. Next day, a mixture of Flumioxazin WDG (water dispersible granules containing 51% of flumioxazin, commercial name: Valor SX, produced by Valent U.S.A.) and emulsifiable concentrate containing Compound [I] (prepared by dissolving Compound [I] with acetone containing Tween 20 (surfactant, sorbitan monolaurate polyglycol ether)) was diluted with a designated amount of water, and applied uniformly on the surface of the soil with a small sprayer.


The treated plants were grown in the greenhouse. The herbicidal activity and phytotoxicity against the vegetable were examined 21 days after the application. The results are shown in Table 4.












TABLE 4










Phytotoxicity



Herbicidal activity
against












Amount of active

Redroot
vegetable











Test compound
ingredient (g/ha)
Crabgrass
pigweed
Tomato














flumioxazin +
25 + 50
9
10
No damage


Compound [I]
50 + 50
10
10
No damage



100 + 50 
10
10
No damage



 25 + 100
9
10
No damage



 50 + 100
10
10
No damage



100 + 100
10
10
No damage



 25 + 200
9
10
No damage



 50 + 200
10
10
No damage



100 + 200
10
10
No damage









As shown in Test example 4, excellent herbicidal effect was provided in the area treated with the composition of the invention. Further, there was no damage found in tomato.


Test Example 5

Plastic pots each having a width of 17 cm, a depth of 12 cm and a height of 7 cm were filled with upland soil, and then transplanted with cucumber and seeded with barnyardgrass, black nightshade and common purslane. Next day, a mixture of Flumioxazin WDG (water dispersible granules containing 51% of flumioxazin, commercial name: Valor SX, produced by Valent U.S.A.) and emulsifiable concentrate containing Compound [I] (prepared by dissolving Compound [I] with acetone containing Tween 20 (surfactant, sorbitan monolaurate polyglycol ether)) was diluted with a designated amount of water, and applied uniformly on the surface of the soil with a small sprayer.


The treated plants were grown in the greenhouse. The herbicidal activity and phytotoxicity against the vegetable were examined 21 days after the application. The results are shown in Table 5.













TABLE 5











Phyto-



Amount of
Herbicidal activity
toxicity













active
Barn-


against


Test
ingredient
yard
Black
common
vegetable


compound
(g/ha)
grass
nightshade
purslane
Cucumber















flumioxazin +
25 + 50 
10
10
10
No


Compound [I]




damage



50 + 50 
9
10
10
No







damage



25 + 100
10
10
10
No







damage



50 + 100
10
10
10
No







damage



25 + 200
10
10
10
No







damage



50 + 200
10
10
10
No







damage









As shown in Test example 5, excellent herbicidal effect was provided in the area treated with the composition of the invention. Further, there was no damage found in cucumber.


Test Example 6

Plastic pots each having a diameter of 21 cm and a height of 20 cm were filled with upland soil, and then planted with potato and seeded with barnyardgrass, crabgrass and ivyleaf morningglory. Next day, on the surface of the soil of the above-mentioned plastic pots, Flumioxazin granules (granules containing 0.25% of flumioxazin, commercial name: Broad Star, produced by Valent U.S.A.), granules containing 0.9% of Compound [I] (prepared according to Formulation example 9), and a mixture of the Flumioxazin granules with the granules containing Compound [I] were applied with hand in a designated amount given by Table 6.


The herbicidal activity and phytotoxicity against the vegetable were examined 14 days after the application. The results are shown in Table 6.













TABLE 6









Amount of





active
Herbicidal activity
Phytotoxicity












Test
ingredient
Barnyard

Ivyleaf
against


compound
(g/ha)
grass
Crabgrass
morningglory
vegetable Potato















flumioxazin
 25
1
5
1
No damage


Compound [I]
100
0
5
1
No damage


flumioxazin +
25 + 100
8
10
7
No damage


Compound [I]









As shown in Test example 6, excellent herbicidal effect was synergistically provided in the area treated with the composition of the invention. Further, there was no damage found in potato.


Test Example 7

Plastic container having a width of about 46 cm, a depth of about 31 cm and a height of about 26 cm were filled with upland soil and planted with grape (variety: Delaware), and then seeded with barnyardgrass, crabgrass and redroot pigweed. On the surface of the soil of the above-mentioned plastic pots, a mixture of Flumioxazin granules (granules containing 0.25% of flumioxazin, commercial name: Broad Star, produced by Valent U.S.A.) and granules containing 0.9% of Compound [I] (prepared according to Formulation example 9) was applied with hand in a designated amount.


The herbicidal activity and phytotoxicity against the grape were examined 14 days after the application. The results are shown in Table 7.













TABLE 7











Phyto-



Amount

toxicity



of active
Herbicidal activity
against












Test
ingredient
Barnyard

Redroot
grape


compound
(g/ha)
grass
Crabgrass
pigweed
Grape





flumioxazin +
200 + 50
10
10
10
No


Compound [I]




damage









As shown in Test example 7, excellent herbicidal effect was provided in the area treated with the composition of the invention. Further, there was no damage found in grape.


Test Example 8

Plastic container having a width of about 46 cm, a depth of about 31 cm and a height of about 26 cm were filled with upland soil and planted with a chestnut tree (variety: Gin-yose), and then seeded with barnyardgrass, crabgrass and redroot pigweed. On the surface of the soil of the above-mentioned plastic pots, a mixture of Flumioxazin granules (granules containing 0.25% of flumioxazin, commercial name: Broad Star, produced by Valent U.S.A.) and granules containing 0.9% of Compound [I] (prepared according to Formulation example 9) was applied with hand in a designated amount.


The herbicidal activity and phytotoxicity against the chestnut were examined 14 days after the application. The results are shown in Table 8.













TABLE 8











Phytoto-



Amount of

xicity



active
Herbicidal activity
against












Test
ingredient
Barnyard

Redroot
chestnut


compound
(g/ha)
grass
Crabgrass
pigweed
Chestnut





flumioxazin +
40 + 200
10
10
10
No


Compound [I]




damage









As shown in Test example 8, excellent herbicidal effect was provided in the area treated with the composition of the invention. Further, there was no damage found in chestnut.


The present invention makes it possible to control various weeds at a low dosage in crop fields, vegetable fields, tree land, non-cultivated land and so on.

Claims
  • 1. A herbicidal composition which comprises N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl)cyclohex-1-ene-1,2-dicarboxamide (flumioxazin) and a compound represented by the formula (I):
  • 2. The herbicidal composition according to claim 1, wherein the weight ratio of flumioxazin:Compound [I] is 1:0.1-1:20.
  • 3. The herbicidal composition according to claim 1, wherein the weight ratio of flumioxazin:Compound [I] is 1:0.2-1:10.
  • 4. A method for controlling weeds which comprises applying N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl)cyclohex-1-ene-1,2-dicarboxamide and the compound represented by the formula (I) jointly or simultaneously to weeds or soil in a place where the weeds grow or will grow, wherein the weight ratio of flumioxazin:Compound [I] is 1:0.01-1:100.
  • 5. The method for controlling weeds according to claim 4, wherein the weight ratio of flumioxazin:Compound [I] is 1:0.1-1:20.
  • 6. The method for controlling weeds according to claim 4, wherein the weight ratio of flumioxazin:Compound [I] is 1:0.2-1:10.
  • 7. The method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are in crop fields, vegetable fields, tree land or non-cultivated land.
  • 8. The method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are in crop fields.
  • 9. The method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are in wheat fields.
Priority Claims (1)
Number Date Country Kind
2006-125006 Apr 2006 JP national