JPH01287004A - Herbicidal method and compound - Google Patents

Abstract

PURPOSE: To well control a wide range of various weeds, especially broad leaf weeds, in the habitat of grain crops after their germination by applying both bifenox and a 3,6-dichloropicolinic acid compound to the habitat. CONSTITUTION: This concentrated type or tank mix type herbicide compound comprising (A) bifenox of the formula, (B) one or more kinds of herbicidally active ingredients selected from 3,6-dichloropicolinic acid (3,6-DCP), its salt and its ester, and one or more kinds of diluents or carriers which are preferably not plant poisons is applied to the habitat of grain crops after their germination in an A:B weight ratio of 30:1 to 3:1. The ingredient A is applied in an amount of 0.25-3.0kg, preferably 0.5-1.5kg, especially 0.5-0.75kg, per ha of the habitat, and the ingredient B is applied in an amount of 0.025-0.15kg. The herbicide compound can well control the weeds, especially Veronica spp. and Matricaria spp. weeds.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for controlling weeds in cereal crops and to herbicidal formulations useful inter alia in said method.

Controlling a wide variety of weeds in crops, such as cereal crops, often requires the use of more than one herbicide. It resists and damages winter and spring crops such as wheat, barley, oats and rye.

It has now been discovered by the present invention that a special combination of herbicides not only achieves extensive weed control but is also unexpectedly effective against weeds, especially broad-leaved weeds, in cereal crops. .

That is, the present invention provides a method for controlling weeds, particularly broad-leaved weeds, in a cereal crop growing area. It consists of applying one or more herbicidal active ingredients selected from the following active ingredients: (1) 3,6-DCP or its salts or esters.

In an embodiment outside the scope of the present invention, in washing with water, the following components are additionally added: (2) a benzoic acid herbicide, dicamba
amba) or 2,3,5-TBA or their salts or estenope (3) Phenoxy acid herbicides such as dichlorprop or 2,4-DB
or salts or esters thereof, (4) dinitrophenol herbicides, i.e. DNOC, dinot
erb) or dinoseb or their salts or esters, (5) benzonitrile herbicides ioxynil or bromoxynil or their salts or esters, and (6) benazo 1 i
It is also possible to apply one or more herbicidally active ingredients selected from n) or their salts or esters.

The method of the present invention is characterized by the use of the above active ingredient (1), but as aspects (2) to (2) outside the scope of the present invention,
It will be appreciated that one or more of the active ingredients under 6) may also be used and that additional herbicidally active compounds may also be used in conjunction with the active ingredients under (1) to (6). If the herbicidal active ingredient is acidic or phenolic, salts or esters may be used, provided that they are not phytotoxic to the crop, i.e. substantially less phytotoxic than the free acid or phenol. It is. The nature of these salts and esters are well known to the art of painting.

The preparation of biphenox, methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate, is described in United Kingdom Patent No. 1232.368 and its use as a herbicide is also described in the literature (Proc.

N, E. IAeed Sci, Conf, 1973.
27.31). Similarly, dicamba, 3,6 dichloro-2-methoxybenzoic acid, which is a benzoic acid herbicide, is described in U.S. Pat. No. 3,013,054 1.
．． 7, also 2°3.6-TBA, i.e. 2,3
, 6-) Riff ■] 11 Benzoic acid is US Patent No. 284
8470 and 3081162'i. The phenoxy acid herbicides disclosed in each specification are a well-known group of compounds. 3, dichlorp Y1bu, which has been widely used for a considerable period of time, is 2-(2,4 dichlorophenoxy)bu1
1 pionic acid...ship name" (- and another name is 2,4=
It is known by the name DP; 2, 4-D
B is 4 - (2,L-dichlorophenoxy)butyric acid, DNOC (chemical name: 2-methyl-4,6-dinitropheno-mo) is a dinitrophenol herbicide. ) is British Patent No. 425295 2,17
protected. Dinoseb is 2-sec -butyl-
4,6-dinitropheno-, a ship name of Le, disclosed in U.S. Pat. No. 2,192,197-R. Dinoterb or 2-tert-butyl-4,6-dinitrophenol is disclosed, for example, in GB 1,126,658. The benzonitrile herbicide Iogyushinyl, 4-monohydroxy 3r5-di-iodobenzo, =, -)
5-dibromo 4--hydroxy-benzonitrile are both disclosed, for example, in Eida Patent No. 977,755.

The chemical structure of J-zolin is
Oxo-3-benzo-thiazolineacetic acid is disclosed in British Patent No. 862,226. 3. 6-DCP is 3,6-dicLl1lopicolinic acid5. And this is US Patent No. 331 'I'J'!
It is disclosed in the specification of No. 9.

For example, cereal crops include 1. The process of the present invention finds greatest utility in the treatment of wheat and barley, particularly winter wheat and spring barley, as well as winter barley, although the process may be used to treat wheat and barley, particularly winter wheat and spring barley, as well as winter barley. Crop susceptibility and the severity of the weed control problem determine the application of herbicidal actives. However--
The application rate of Niji fennokuzu is 0.00% per hectare.
25”-3, old (GS preferred is 0 per hectare/month)
．． 5 ==-・1.5 kg and particularly preferably 1 hectare・
... 0.5-0.75 kg per le.

In the following text, the above (1,) -・-(6
) The preferred application amount of component ' is described below. The application rate of components derived from , acid or soSnol is free acid equivalent or phenol equivalent.

Benzoic acid herbicides i.e. dicamba or 2,3.6-TBA
When using mortise, the application rate of tenons is 0.05 to 0.2 kg per hectare, and the ratio of Bifuenotus to benzoic acid herbicide is 60:1 to 1:1, preferably 30:1.
1 to 4:1, when the benzoic acid herbicide is wet with an alkali metal salt, such as a sodium salt or a potassium salt,
Alternatively, it can be used in the form of its esters, such as C1-C, alkyl esters.

As a phenoxy acid herbicide, dichloroprop or 2
．． 4-DB is used, and its preferred application rate is 0.1 to 3.5 kg per hectare, and the ratio of bifenox to phenoxy acid herbicide is 30:1 to 1:15, especially 8: 1=1:6. Particularly preferred embodiments include 0.5 to 0.75 kg per hectare of bifuenox, and 1.5 to 3.0 kg per hectare of phenoxy acid herbicides.
It is applied at the rate of kg. Phenoxy acid herbicides are suitably used in the form of their salts, such as alkali metal salts, especially sodium salts or potassium salts or amine salts or ammonium salts. Ester forms of phenoxy acid herbicides Examples include those containing 1 to 8 carbon atoms in the ester group, such as ethinopeisobutyl and butylnisder.

Dinitrophenol herbicide Hirucho) N OC.

When dinodelb or dinoceb is used, the application rate is preferably between 0.5 and .5 O per hectare.
kg, and more preferably 0.5=2.0 kg per 1-phthalate, especially in the case of dinodelb or dinoceb. The ratio of the amount of Bifuenox to the Ginijo-ropuunol herbicide is preferably 6:1 to 1:20, and more preferably 3:1 to 1:6. Examples of suitable salt forms of di-trophenol herbicides may be salts with inorganic or organic bases, especially amino and ammonium salts. Examples of Nisdel include organic acids such as Nisdel carboxylic acids such as dinocebu acetate, sprue may be used.

The benzonitrile herbicides are ioxynil or bromoxynil, which are used in doses of 0.05 to 0.0% per hectare.
Preferably it is applied at a rate of 5 kg, more preferably from 0.1 to 0.35 kg per hectare. The weight ratio of bifenox to benzonitrile herbicide is preferably 60:1 to 1:2, more preferably 15:1 to 2:1. In a special embodiment, both ioxynil and bromoxynil are used in combination with bifenox, in which case the preferred application rates and weight ratios are as above, based on the total weight of both ioxynil and bromoxynil. Preferred salt forms of ioxinil and bromoxynil are the alkali metal salts, such as the sodium and potassium salts. Suitable esters include ioxynyl octanoate and bromoxynyl octanoate.

When using benazoline, it is applied at a weight rate of 0.05 to 0.25 kg per hectare.

The weight ratio of bifuenox to benazoline is preferably 60:
The ratio is 1 to 1:1, more preferably 15:1 to 5:2. Suitable salt forms of benazoline include the alkali metal salts, particularly the sodium and potassium salt forms. Preferred esters are those containing 1 to 4 carbon atoms in the ester group, especially the ethyl ester.

3. When using 6-DCP, preferably 0.025 to 0.15 kg of this per hectare.

More preferably 0.05 to 0.1 k per hectare
Apply at the rate of g. Bifuenocus vs. 3. 6-DPC
A preferred weight ratio is 30:1 to 3:1, and a more preferred ratio is 15:1 to 5:1. Examples of salt forms of 3.6-DPC are the alkali metal salts, such as the sodium and potassium salts, and the amine or ammonium salts, such as the monoethanolamine salt. Examples of esters given are those containing 1 to 8 carbon atoms in the ester group.

The method of the present invention can be applied to cereal crops at the one leaf stage.
It is preferable to carry out the process at an intermediate point between the stage and the formation of the second node.

When Bifuenox is used in combination with benzoic acid herbicides, the weed species Stellariamed
ia), Polygonum 5pp
), Spergula alpensis (Spergula a
rvensis),Tripleurospermum maritum
Particularly good control has been observed for the following species: imum), Viola 5pp and Veronica 5pp.

The weed species Gallium abarin (G (11iumapar)
1ne), Stellaria mejia and Veronica spp. have been observed to achieve particularly good control.

When Bifuenox was used in combination with dinitrophenol herbicides, weed species Galeobsis tetrahyte (G(11)
eopsis tetrahit), Fumaria officinalis (11i
s), Polygonum comporvulus
Particularly good control has been observed for gallium abarin (G. convolvulus) and gallium abarin.

When Bifuenox is used in combination with benzonitrile herbicides, the weed species Matricaria sp.
p), Polygonum sp. and Gallium abarin have been observed to achieve particularly good control.

Particularly good control has been observed to be achieved against Stellaria media, Gallium abarin and Viola species when Bifuenox is used in combination with Benazoline.

Particularly good control achieved against the weed species Veronica sp. and Matricaria sp. has been observed when Bifuenox is used in combination with 3.6-DCP.

Examples of additional herbicidally active compounds which can be used in combination with bifuenox and the active ingredients (1) to (6) above include MCPASMCPB and mecopr.
op), all of which are well-known herbicides and have been described in the literature.
(“Pe5ticide Manu(11”, fi
ftedition, 1ssued by the
Br1tish Crop ProtectionC
).

Bifuenox and the above herbicidal active ingredients (1) to (6) and optionally additional herbicidal active compounds can be applied to the crop growing area at the same time or at different times. In the latter case, the lungs! For IN (plural) 1'''F11 (r=·, t between i, lj, ? is preferably short, e.g. 10 or more -t; 3g +,...).

stomach. However, it is far more difficult to apply the compound to be applied simultaneously as a mixture.
In order to simplify manufacturing, storage and transportation, herbicidal formulations are usually applied in a concentrated form, to the extent necessary, resulting in an application rate of 20. Dilute with water 1)
When diluting ,... [,7 is generally applied to crop areas H”
C: 116 times the active compound is active. Generally 1-90%, preferably 15-85% of various herbicidally active ingredients (5) non-phytotoxic carriers or diluents (1 or 2) ) and the train is 1″.

Concentrated formulations form part of the invention Q2
3) There is therefore provided a formulation for a reduction!, ゛f, which can be used specifically, but not exclusively, in the process of the present invention. Nox and Saraj
, ″′, present invention) aspects and 12, r(1) 3. 6-r)
Cp or +-salt or T sprue, as an embodiment outside the present invention (2) a benzoic acid herbicide, i.e. dicamba or 2,3.6
-TBΔ or their salt b t-<L;
(3) No-cho = ノ''Y-Silic acid-based removal 'Removal 1') Dichlorb D 7' or 2.4-DB 戊はI-cho (f) m MoI, <Ha-cho, sprue, (4 ) C, Ziplua' or dinotb, < fJ, their salts or -"i'-sprue, (5) benzo-1l-lyl herbicides. The stimulant is iodine,
(6) benozoline or a salt thereof, or one or more of the following. The active ingredient is combined with one or more non-phytotoxic carriers or diluents (C), and in this formulation, the weight of each active ingredient (1) - (6) The ratio is related to the present invention (as described in 2 during pre-heating).

The condensation formulation of the present invention will normally be in the form of a wettable powder, an emulsifiable acondensate, or an aqueous suspension. Is the formulation of an aqueous suspension and a wettable powder suitable for use in the method 1 of the present invention with zero tolerance to grain crops? The plant toxin properties of ♂・ are concentrates that can be emulsified. Even 1 point is selfishly low.

The wettable powder contains an intimate mixture of the herbicidal active ingredient and 71 or more inert carriers and optional surfactants. Examples of inert clays include 7 attapulgite clays,
Selected from montmorillonite clay, clay algae, kaslin, mica, talc and purified silicates: I''). Effective surfactants are sulfonated lignin, booklin sulfonate and condensed naphthalene sulfone, argyl saccine). Examples of alkyl benzene sulfonates, alkyl nalphgoates, and non-menic ν2 surfactants are those found among the 73-north compound.

The emulsifiable concentrate consists of a herbicidally active ingredient and a surfactant dissolved in a suitable solvent or solvents. Suitable surfactants may be selected, for example, from those mentioned in connection with the wettable powders. Suitable solvents include 1-alkylated benzene, 0-1-1 toluene, heavy aromatic nacculins, glycols, and cyclic getones.

Aqueous suspensions and aqueous liquids contain herbicidal active ingredients suspended or dissolved in water or a suitable melt, respectively, and desired surfactants, thickeners, antifreezes, or preservatives. do. Suitable surfactants are selected from those mentioned above in connection with the wettable powders. Use thickening agent A
If this is the case, this means that the appropriate cell
Usually selected from L:l if an antifreeze agent is required.
Use Grini 1-Sword/Sword for. Preservatives include a wide range of substances such as various paraben antibacterial agents, phenolics,
mercuric nitrate and formyldehyde.

Another formulation method is to form a herbicide formulation by mixing two or more herbicidal active ingredients with water in a spray tank immediately before using the herbicidal formulation. obtain. Therefore, water acts as a carrier of non-phytotoxins.
t, ank m1xes), which forms another aspect of the present invention. Preferably, the above-mentioned weight ratios are suitable.

“Tankomics type” in the claims of this specification
The term tank m1x) J refers to the method of packaging the multiple components forming the formulation of the present invention. That is, the plurality of components are stored in separate containers, and when used, they are added together into a tank for preparing agricultural propellants, and then the required amount of water is added to dilute in the tank. It is a type of compound.

The following roadside is illustrative of a concentrated herbicide formulation according to the present invention. When the herbicide component is an acid or a phenol derivative, the amount of the component is based on acid equivalents or phenol equivalents.

Among these roadside examples 4 and 16 are examples of the present invention, and the others are reference examples.

Examples 1-9 Wettable powders were prepared using the following raw ingredients.

Weight % (1) Bifuenox 50 Ioxynyl 5 Disodium salt of condensed naphthalene sulfonic acid Ethoxylated alkylphenol 4 Pyrogenic silica 5 Montmorillonite Added to total amount of 100 (2) Bifuenox 42 Bromoxynyl 6 Sodium lauryl sulfate 5 Sodium lignin sulfonate 3 Precipitation Method silica 8 Kaolin Added until the total amount reached 100 (3) Biphenox 48 Benazoline (ethyl ester) 4 Ethoxylated nonylphenol 4 Sulfite method leachate powder 4 (Sulfite lye
powder) Pyrogenic silica 5
Add attapal guide until the total amount is 100 (4)
Bifuenox 403, 6-D
CP (monoethanolamine salt) 4 Sodium lauryl sulfate 4 Sodium lignin sulfonate 3 Precipitated silica 8 Kaolin Added until total 1100 (5)
Bifuenox 202.4~DB
(Potassium salt) 30 Ethoxylated alkylphenol 2 Sulfite method leachate powder 4 Pyrolysis method silica
5 Attapal guide Add until the total amount is 100 (6) Bifuenox 20
Dichlorprob (potassium salt) 40 Sodium dialkyl sulfo 3 Succinate lignosulfonate 2 Microcrystalline silica 7 (micronised 5
ilica) Diatomaceous earth Add until the total amount is 100 (7) Bifuenox 4
5 Ioxynyl 2.5 Bromoxynil Trisodium lauryl sulfide Disodium lignin sulfonate
3 Precipitation method silica 5 Montmorillonite Add until the total amount reaches 100 (8) Bifuenox 40
2,3.6-TBA (sodium salt)
5-sodium lauryl sulfate 3-sodium lignin sulfonate 3-precipitation silica
4 Kaolin Add until the total amount is 100 (9) Bifuenox
40 Dicamba (sodium salt) 4 Ethoxylated alkylphenol 4 Lignosulfonate
2 Pyrolysis Silica
The herbicidal active ingredients were carefully mixed with special excipients in a conventional mixing device on each side until the total amount of trisodium aluminosilicate was 100%. fluid en
ll) in the size range of 1-10 microns - one, 1'
Pulverized sea urchin.

Examples 10 to 21 Emulsifying concentrates containing the following components: 2. ii, i, made l1li products.

did.

Military science % αO biphenox 21] Ioxynyl (octanony ■・) 3 Calcium dodecylbenzene 4 Sulfonate alkylphenol 4 Cypolyoxy 2 Ethylene ethanol Cyclohexanone 35 Xylene
The total amount is 100 [addition at 01] Biphenox 20 Prothousynyl (octanoni...) 4 dodecylbenzenesulfonic acid
3 Amine salt Polymexyethylene triglyceride 3 Cyclohexanone 30 Add until total amount of orthochlorotoluene]00017) Bipuenox 2
0 Bezuzoline (yellow, blue)', Thrall) 2 Calcium dodecylbenzene 2 Sulfonate Ethoxylated alkyl group 4 Isophorone
35 Heavy Aromatic Nafuna Added OJ until the total amount reached 100 Bifuenox 6D
N OC20 Calcium dodecylbenzene 3 Sulfonate etoysylation °rKylphenol 3 Cyclo-xanone 25 Heavy aromatic naphtha Added until total amount 10000 Bifuenox 20 Dinoterb 10 Alkylaryl sulfonate 2 Alkylphenoxypolyoxy 4 Ethylene ethanol Isoboron 30 The total amount of orthochlorotoluene will be 100 r; ゛Additional 0ω Biphenox 15 Dinoceb 15 4-Amine salt of dodecylbenzenesulfonic acid Polyoxytinyl nontriglyceride 3 Isophorone
20 Heavy aromatic naphza total amount 1 () Added until it becomes 000 Bifuenox 203
,5-D(:I'
4 Calcium dorsylbenzene 4 Sulfone toethoxylated alkylpenol 4 Isophorone
Add 30 heavy aromatic naphtha until the total amount becomes 100 (1'l) Bifuenox
152.4-DB (isopropyl ester>
30 Alkylaryl sulfone 1, 4 polyoxy, co:thi 1/triglyceride 2 cyclohexanone 25 xylene Total amount liter
Addition until ° becomes 0Φ Hifu 1-nox
15 Dik 11 Rubrop (butyl ester) 45 Door's 3-amine salt of silbenzenesulfone L. Alkylphenoxypolyoxy 3 Ethylene ethanol cyclohexanone 25 Heavy aromatic naphtha Added until the total amount reached 100 Bifuenox 20 Ioxynyl (octanoate) 1.5bromoxynil (octanoate) 2calcium dodecylbenzene
3 Sulfonate alkyl phenoxy polyoxy 4 Ethylene ethanol isophorone 30 Add until the total amount of orthochlorotoluene becomes 100 (a) Bifuenox 252,
3.6-TBA (ester) 3 Calcium dodecylbenzene 3 Sulfonate ethoxylated alkylphenol 3 Isophorone
30 Orthochlorotoluene Add until the total amount reaches 100 (21) Biphenox 20 Dicamba 2 Alkylaryl sulfonate 4 Alkylphenoxypolyoxy 2 Ethylene ethanol Cyclohexanone 25 Xylene
The added herbicidal active ingredient was added to a suitable solvent (single or plural) under stirring until the total amount reached 100%, and optionally heated to easily dissolve the ingredient. Next, surfactant was added.

After dissolution, the solution was filtered to remove insoluble impurities.

Examples 22-24 An aqueous suspension was prepared from the following components.

Weight/Volume% (22) Biphenox 40 Ioxynyl (sodium salt) 4 Ethoxylated nonylphenol 3 Hydroxymethyl cellulose 2 Silicon antiform 0.1 Water Total volume 10
Add until it reaches 0 (23) Bifuenox
35 Bromoxynil (potassium salt) 3.
5 Ethotosylated nonylphenol 2.5 Hydroxymethyl cellulose 1.7 Silicon antiform 0.1 Water Add until the total volume is 100 (24) Bifuenox
48 Benazoline (potassium salt) 8 Sodium laurylsal 3 Phateacpalguide 1.5 Silicon antiform 0.15 Water Mix the added herbicide ingredients with surfactant and foam suppressant until the total volume is 100, then add to the water. A crude aqueous suspension was formed with vigorous stirring. This was then kept under humid conditions to reduce the particle size of the herbicidal active ingredient to 0.5-20 microns. An aqueous suspension of a thickening agent or suspending agent (hydrate) was added to this wet temperature product.

Example 25 below is an example of a test method for determining the effectiveness of the methods and formulations of the invention.

Example 25 (Test Method) An appropriate amount of a formulation product (e.g., one of the concentrated formulation products of Examples 1-24) is placed in a microspray.
The dispersion was completed by adding to the water in a -5 player) and stirring. Adjust sprayer to 40psi
(approximately 2.72 atmospheres) (approximately 2.8 kg/cm") with a volume equal to 20011/hk.
Standard nozzle (Al 1man) that injects ed jet)
No. 0) was equipped on the sprayer.

The product of the present invention was applied after both the crop and the weeds had germinated, but the application period was changed to when the crop was in the three-leaf stage (31eaf).
stage) to early stem elongation at various times. The timing of application to weeds can also be varied at various times from the cotyledon stage to the seedling stage of weed growth.

Claims (11)

[Claims] (1) The following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Bifenox having I and 3,6-
A method for controlling weeds in a cereal crop growing area, comprising applying one or more herbicidal active ingredients selected from DCP or its salts or esters to the cereal crop growing area after the cereal crops germinate. (2) The method according to claim (1), characterized in that Bifuenox is applied at a rate of 0.25 to 3.0 kg per hectare of cereal crop growing area. (3) Bifuenox 0.5 to 1.5 per hectare
The method according to claim (2), characterized in that it is applied at a rate of 1.0 kg. (4) Bifuenox 0.5-0.7 per hectare
The method according to claim (3), wherein the method is applied at a rate of 5 kg. (5) 3,6-DCP from 0.025 per hectare
The method according to any one of claims (1) to (4), characterized in that it is applied at a rate of 0.15 kg. (6) A concentrated type or tank characterized by combining one or more of bifuenox and 3,6-DCP or its salt or ester with one or more non-phytotoxic diluents or carriers. A mix-type herbicidal compound. (7) The weight ratio of Bifuenox to 3,6-DCP is 30:
Claims characterized in that the ratio is 1 to 3:1 (6
). (8) The herbicidal formulation is a concentrated formulation and has a concentration of 15 to 85%.
% of herbicidal active ingredient. (9) The herbicidal formulation according to claim (8), characterized in that the herbicidal formulation is an emulsifiable concentrate, an aqueous suspension or a wetting powder formulation. (10) A herbicidal formulation according to claim (6) as described in any of Examples 4 and 16 and substantially as hereinbefore described. (11) One or more herbicidal active ingredients selected from bifuenox and 3,6-DCP or its salt or ester are applied to the cereal crop growing area after the cereal crops germinate to control weeds in the cereal crop growing area. A herbicidal formulation according to any one of claims (6) to (10) for use in a control method.