JPH0219084B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to herbicidal compositions. British Patent Application No. 2064537 states that 3-(3
-methyl-4-isopropylphenyl)-1,1
-The compound dimethylurea has been described to be effective in controlling weeds. This compound can also act as a synergist when mixed with another herbicide compound, so that it can be used as a synergist with some herbicides.
(3-methyl-4-isopropylphenyl)-1,
It has now been discovered that mixtures with 1-dimethylurea exhibit an unexpected synergistic effect. Therefore, the present invention provides (i) a compound having the following general formula or a salt or ester thereof; In this formula, each of X ¹ and X ² independently represents an iodine atom, a bromine atom or a chlorine atom; (ii) a compound having the following general formula or a salt or ester thereof; In this formula, each of X, Y and Z independently represents a hydrogen atom or a halogen atom or an alkyl group or a _CF3 group, R represents a hydrogen atom or an alkyl group, and n is 0, 1,
2,3 or 4; (iii) 1-bendithiazol-2-yl-1,3-
Dimethylurea; (iv) 2,6-dinitro-N,N-dipropyl-4
- trifluoromethylaniline; and (v) a compound having the following general formula or a salt or ester thereof: In this formula, R ¹ is a C ₁ -C ₄ alkyl group; together with at least one compound selected from
3-(3-methyl-4-isopropylphenyl)
A herbicide composition containing -1,1-dimethylurea (hereinafter referred to as compound A) is provided. The composition of the invention comprises two or more compounds from one of groups (i), (ii) and (v) and/or
It may contain two or more compounds from different groups of (i), (ii), (iii), (iv) and (v). However, preferably the composition comprises groups (i), (ii), (iii), (i)
v)
and (v). The invention further provides a method for combating undesirable plant growth in an area, comprising applying to the area Compound A and at least one compound selected from (i) to (v) above. do. In the formula, each of X ¹ and X ² preferably independently represents an iodine atom or a bromine atom,
And preferably X ¹ and X ² are the same. Compound (i) may be a free phenol of the formula, or a salt or ester thereof. Suitable salts include alkali metal salts, especially sodium or potassium salts and amine salts. Suitable amine salts have, for example, up to 3 organic groups bonded to the nitrogen, and the organic groups have, for example, 10
Includes salts of amines containing up to 5 carbon atoms and optionally substituted, for example, by hydroxy groups or halogen atoms. Suitable esters are, for example, alkyl esters having, for example, up to 20, in particular 6 to 12, carbon atoms in the alkyl moiety. Preferably, compound (i) is free phenol or its octanoate ester. The alkyl groups represented by R, X, Y or Z in the formula preferably have up to 4 alkyl groups. In the formula, each of X, Y and Z preferably independently represents a chlorine atom, a hydrogen atom or a methyl group. Most preferably, one of X, Y and Z is a hydrogen atom and the remaining two substituents are independently selected from a chlorine atom and a methyl group. Preferably R is a methyl group or a hydrogen atom, and n is 0, 1 or 2. Typical compounds of group (ii) are 2-(4-chloro-2-methylphenoxy)propanonic acid, 2
-(2,4-dichlorophenoxy)propanonic acid,
4-chloro-2-methylphenoxyacetic acid, 2,4
-dichlorophenoxyacetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, 4-(4-chloro-2-methylphenoxy)butanoic acid, and salts and esters thereof. A compound of group (ii) may be the free acid of formula or a salt or ester thereof. Suitable salts include alkali metal salts, especially sodium or potassium salts, alkaline earth metal salts such as magnesium salts and amine salts. Suitable amine salts have, for example, up to 3 organic groups bonded to nitrogen, and the organic groups contain, for example, up to 10 carbon atoms, and are optionally separated, for example by hydroxy groups or halogen atoms. Includes salts of amines that are substituted alkyl groups. Suitable esters are, for example, alkyl esters having up to 10 carbon atoms in the alkyl part, such as the various octyl ester isomers. Preferably group (ii)
The compound is the free acid or potassium salt. Compounds of group (ii) have an asymmetric carbon atom in which R is a group other than a hydrogen atom and can therefore exist in two optically active forms. It is to be understood that the invention includes the use of any isomer or any mixture thereof. The alkyl group R ¹ in the formula is preferably a butyl group. Most preferably R ¹ is a secondary or tertiary butyl group. A typical compound of group (v) is 2-tert-butyl-
Includes 4,6-dinitrophenol, 2-sec-butyl-4,6 dinitrophenol, and salts and esters thereof. A compound of group (v) may be a free alcohol of formula or a salt or ester thereof. Suitable salts include alkali metal salts, especially sodium or potassium salts, alkaline earth metal salts such as magnesium salts, ammonium salts and amine salts. Suitable esters are derived from substituted or unsubstituted carboxylic acids, especially alkanonic acids. Preferably, the compound of group (v) is a free alcohol or its acetate. The weight ratio of compound A to the compound selected from (i) to (v) varies widely depending on the intended use. Preferably, the ratio is 1:50 to 50:1,
Preferably the ratio is 1:20 to 20:1, especially 5:1 to 1:5. Suitably, the application rate of each compound is
It is in the range of 0.05 to 5Kg/ha. Particularly preferred application rates for certain binary mixtures include, for example, 0.05 to 2.5 Kg/ha of the compound of group (i) and the compound
A0.3 to 3 Kg/ha; compounds of group (ii) 0.1 to 3.5
Kg/ha and compound A0.3 to 3Kg/ha; compound (iii)
0.3 to 4Kg/ha and compound A0.3 to 3Kg/ha
ha; Compound (iv) 0.25 to 3 Kg/ha and Compound A 0.25
and 0.25 to 3 Kg/ha of compound of group (v) and 0.25 to 3 Kg/ha of compound A. The compositions and methods of the present invention may of course include compounds (i) or
Due to the properties of (v), it can be used to control weeds in a wide range of crops. Typical crops include, for example, cotton, soybeans, large plantation crops such as sugar cane or grapes, and cereals such as wheat, barley, corn and sugar corn, among others. Mixtures containing compounds of group (v) are also particularly useful in leguminous crops such as peas and broad beans. A wide range of broadleaf and grassy weeds are controlled. It can be applied before germination or
Alternatively, it may preferably be applied after germination. For some applications, it may also be desirable to apply additional herbicides, especially when resistant weeds are present. for example,
In cases where cereal crops are highly infested with wild oats, compounds (i) to (v) together with one or more of the compounds (i) to (v) and compound A, which have a special narrow spectrum of action, may be used. , and British Patent No.
1164160, such as N-benzoyl-N-(3,4-dichlorophenyl)-2-
Ethyl ester of aminopropionic acid, or N
- Racemic mixtures or levorotatory isomers of the methyl or isopropyl esters of benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionic acid or herbicides with a broad spectrum of action such as triazines, e.g. cyanazine. , atrazine or simazine are advantageously applied. Other suitable compounds that may be present as the third component include metolachlor, chlortoluron, isoproturon and dichlofopmethyl. The composition of the invention preferably also has one or two
Contains more than one type of carrier. The carrier can be any material that facilitates application to the area to be treated or forms the active ingredient to facilitate storage, transportation, or handling. The carrier may be solid or liquid, and includes substances that normally become liquid when compressed with a gas;
Any carrier commonly used to formulate herbicidal compositions can be used. Suitable solid carriers are natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earth; magnesium silicates, such as talc; aluminum magnesium silicates, such as attapulgite and vermiyukilite; aluminum silicates,
such as kaolinite, montmorillonite and mica; calcium carbonate; calcium sulfate; synthetic hydrated silicon oxides and synthetic calcium or aluminum silicates; elements such as carbon and sulfur; natural and synthetic resins such as coumaron resin, polyvinyl chloride, and styrenic polymers and copolymers; solid polychlorophenols; bitumen; waxes such as beeswax, paraffin wax, and chlorinated mineral waxes; and solid fertilizers such as superphosphates. Suitable liquid carriers are water; alcohols such as isopropanol and glycols; acetone, methyl ethyl ketone, methyl isobutyl ketone and chlorhexanone; ethers; aromatic or araliphatic hydrocarbons;
Examples include benzene, toluene and xylene; petroleum fractions such as kerosene and light mineral oils; chlorinated hydrocarbons such as carbon tetrachloride, perchlorethylene and trichloroethane. Mixtures of dissimilar liquids are often suitable. Agricultural compositions are often formulated and distributed in concentrated form, which is then diluted with water before application. The presence of a small amount of carrier, a surfactant, aids in this dilution purpose. The surfactant may be an emulsifying agent, a dispersing agent or a wetting agent, which may be non-ionic or ionic. Examples of suitable surfactants include sodium or calcium salts of polyacrylic acids and ligninsulfonic acids; fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule and ethylene oxide and/or propylene. Condensation products with oxides; fatty acid esters of glycerol, sorbitan, sutucarose or pentaerythritol; condensates of these esters with ethylene oxide and/or propylene oxide; fatty alcohols or alkylphenols, such as p-octylphenol or p-octyl condensation products of cresol with ethylene oxide and/or propylene oxide; sulfates or sulfonates of these condensation products; alkaline earth metal salts of sulfuric esters or sulfonic esters containing at least 10 carbon atoms in the molecule, preferably Sodium salts, such as sodium lauryl sulfate, sodium secondary alkyl sulfate, sodium salt of sulfonated castor oil, and sodium alkylaryl sulfonates, such as sodium dodecylbenzene sulfonate; and polymers of ethylene oxide and combinations of ethylene oxide and propylene oxide. Copolymers are included. The compositions of the invention can be formulated, for example, in the form of wettable powders, powders, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Lubricating powders usually contain 25, 50 and 75% by weight of active ingredient and, besides an inert solid carrier, usually contain 3% by weight of active ingredient.
-10% by weight of dispersant and, if necessary, 0-
Contains 10% by weight of stabilizers and/or other additives, such as penetrants or stickers. Powders are usually formulated in the form of powder concentrates with a composition similar to that of wettable powders but without dispersants, and are usually further processed on site to give a composition containing 0.5-10% by weight of active ingredient. Diluted by carrier. Granules are usually prepared with dimensions of 10 to 100 BS mesh (1.676-0.152 mm) and can be produced by agglomeration or impregnation methods. Generally, granules contain 0.5-25% by weight of active ingredient and 0-10% by weight of additives, such as stabilizers, slow release modifiers.
and a binder. Emulsifiable concentrates usually contain, in addition to the solvent, a co-solvent and, if necessary, 10-50% w/v of active ingredient, 2-20% w/v of emulsifier and 0
-20% w/v of other additives, e.g. stabilizers,
Contains penetrants and corrosion inhibitors. Suspension concentrates are usually formulated to yield stable, non-settling, flowable products, typically 10-75% by weight.
active ingredients, 0.5-15% by weight of dispersing agents, 0.1-10% by weight of suspending agents, such as protective colloids and thixotropic agents, 0-10% by weight.
Other additives, such as defoamers, corrosion inhibitors, stabilizers, penetrants and adhesives, and water or organic liquids in which the active ingredient is substantially insoluble, to prevent settling or to prevent water from freezing Certain organic solids or inorganic salts may be present in dissolved form in the formulation as agents. Also within the scope of the invention are aqueous dispersions and emulsions, for example compositions obtained by diluting wettable powders or concentrates according to the invention with water. The emulsion may be either water-in-oil or oil-in-water and may have a thick "mayonnaise" consistency. The compositions of the invention may also contain other ingredients, such as compounds with insecticidal or fungicidal properties. The following examples illustrate the invention. General Procedures The test conducted was a foliar spray test in which plant seedlings were sprayed with a formulation containing the test compound. A variety of test plants were used, including blakgrass, dogfish, dogbroom, and wild grass. The soil used in the test was horticultural soil.
Seedlings of Inufuguri and Wild Karasumugi had no or one adult leaf, and seedlings of Black Grass and Inuhozuki had two or three adult leaves. The formulation used in the study was 0.4% alkylphenol/ethylene oxide concentrate, available under the trade name TRITON X-155.
A solution of the test compound or test mixture in acetone containing % by weight was prepared by diluting with water. The acetone solution was diluted with an equal volume of water and the resulting formulation was applied at four planned application rates to generate a range of reactions. Three replicate pots were used for each treatment. Seedlings of untreated plants were used as controls. After a specified number of days of treatment, the toxicity to the plants was visually evaluated compared to an untreated control, expressed on a scale of 0 to 9, with 0 meaning no effect and 9 meaning death. Ta. The obtained results are subjected to a standard probit analysis using a computer to calculate the application amount of each compound or each mixture required to kill 50% of the test plants, expressed in kg/ha, and calculate this application amount. below
It is called GID ₅₀ application rate. If a mixture of herbicides A and B acts additively, the value of GID ₅₀ for A and B in the mixture would be expected to be given by equations (i) and (ii) below. . GID ₅₀ of B in the mixture = a/α+a/b (i) GID ₅₀ of A in the mixture = (GID 50 of B in the mixture
GID ₅₀ )×α (ii) In these formulas, a=GID ₅₀ when only A is used b=GID ₅₀ when only B is used α=weight ratio of compound A to compound B in the mixture. It is. If the measured GID ₅₀ value is actually smaller than the calculated value, the mixture has a synergistic effect (in other words, A and B have a synergistic effect on each other). The results of the test are shown in the table below. The value of GID ₅₀ is the actual measured value, expressed in Kg/ha,
Calculated values are shown in parentheses after the measured values. Example 1 This example was performed using the following compounds. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 3,5-dibromo-4-hydroxybenzonitrile (commercial herbicide "Bromoxynil") Results From the table shown (Table 1), it can be seen that this mixture has a synergistic effect on all types of plants tested, i.e. the actual amount of application of the mixture required to kill 50% of the tested plants. It can be seen that is smaller than the calculated value.

[Table] Example 2 This example was carried out using the following compounds. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 3,5-dibromo-4-hydroxybenzonitrile octanoate ester From the table showing the results (Table 1), It can be seen that this mixture has a synergistic effect on dog pufferfish and wild grass, and has an almost additive effect on dog pufferfish and blackgrass.

[Table] Example 3 This example was carried out using the following compounds. A: 3-(3-Methyl-4-isopropylphenyl)-1,1-dimethylurea B: Monomethylamine salt of 2-(2,4-dichlorophenoxy)-propanoic acid (commercial herbicide The results are shown in Tables a and b, and these results indicate that although the synergist effect of this mixture on dog blowfish was observed on the 9th day after treatment,
This shows that the synergist effect was exerted on the dogfish only 5 days after treatment. No synergistic effect was observed against blackgrass.

【table】

[Table] Example 4 This example was carried out using the following compounds. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 2-(4-chloro-2-methylphenoxy)-
Potassium salt of propanoic acid (commercial herbicide ``Mecoprop'') The results are shown in Tables a and b, and these results show that this mixture was effective against blackgrass and doggrass after only 5 days. It has been shown that it exerts a synergistic effect on. No synergistic effect was observed on dog blowfish.

【table】

[Table] Example 5 The following compounds are used in this example. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: (2,4-dichlorophenoxy)acetic acid (commercial herbicide "2,4-D") 6 The results of the evaluation after 1 day are shown in Table 1. A synergistic effect can be clearly seen.

[Table] Example 6 The following compounds were used in this example. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: (4-chloro-2-methylphenoxy)acetic acid (commercial herbicide "MCPA") Results evaluated after 12 days are shown in the table. A synergistic effect can clearly be recognized.

[Table] Example 7 The following compounds were used in this example. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 1-benzothiazol-2-yl-1,3-
Dimethylurea (commercial herbicide "Methabenzthiazuron") The results evaluated after 12 days are shown in the table and show that the tested mixture was effective against both dog pufferfish and dog pufferfish. This indicates that it exerted a meaningful synergistic effect against

[Table] Example 8 The following compounds were used in this example. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 2,6-dinitro-N,N-dipropyl-4
- Trifluoromethylaniline (commercial herbicide "Trifluralin") The results evaluated after 13 days are shown in the table and show that the tested mixture exhibits synergistic action. It shows.

【table】

[Table] Example 9 The following compounds were used in this example. A: 3-(3-methyl-4-isopropylphenyl)-1,1-dimethylurea B: 2-tert-butyl-4,6-dinitrophenol (commercial herbicide "Dinoterb") The results evaluated over a period of 6 days are shown in the table and show that the tested mixtures exerted a significant synergist effect.

【table】

【table】

Claims (1)

[Claims] 1 (i) A compound having the following general formula or a salt or ester thereof: In this formula, each of X ¹ and X ² independently represents an iodine atom, a bromine atom or a chlorine atom; (ii) a compound having the following general formula or a salt or ester thereof; In this formula, each of X, Y and Z independently represents a hydrogen atom or a halogen atom or an alkyl group or a _CF3 group, R represents a hydrogen atom or an alkyl group, and n is 0, 1,
2,3 or 4; (iii) 1-benzothiazol-2-yl-1,3-
Dimethylurea; (iv) 2,6-dinitro-N,N-dipropyl-4
- trifluoromethylaniline; and (v) a compound having the following general formula or a salt or ester thereof: In this formula, R ¹ is a C ₁ -C ₄ alkyl group; together with at least one compound selected from 3
-(3-methyl-4-isopropylphenyl)-
A herbicide composition comprising 1,1-dimethylurea. 2. The composition according to claim 1, wherein X ¹ and X ² in the formula both represent an iodine atom or both represent a bromine atom. 3. A composition according to any of claims 1 or 2, wherein the compound of group (i) is a free phenol of the formula, or an alkali metal salt, amine salt or alkyl ester thereof. 4. A composition according to claim 3, wherein the compound of group (i) is a free phenol of formula or an octanoate ester thereof. 5. A composition according to any one of claims 1 to 4, wherein any alkyl group represented by R, X, Y or Z in the formula has up to 4 carbon atoms. 6. The composition according to claim 1, wherein each of X, Y and Z in the formula independently represents a hydrogen atom, a chlorine atom, or a methyl group. 7. The composition of claim 6, wherein one of X, Y and Z in the formula is a hydrogen atom and the other two remaining substituents are independently selected from a chlorine atom and a methyl group. 8. The composition according to any one of claims 1 to 7, wherein R in the formula represents a hydrogen atom or a methyl group. 9 The compound of group (ii) is 2-(4-chloro-2-methylphenoxy)propanoic acid, 2-(2,4-dichlorophenoxy)propanoic acid, 4-chloro-2-
Methylphenoxyacetic acid, 2,4-dichlorophenoxyacetic acid, 4-(2,4-dichlorophenoxy)
9. The composition according to any one of claims 1 to 8, which is butanoic acid or 4-(4-chloro-2-methylphenoxy)butanoic acid or a salt or ester thereof. 10. The compound of group (ii) is the free acid of formula, or is an alkali metal salt, alkaline earth metal salt, amine salt or alkyl ester thereof;
A composition according to any one of claims 1 to 9. 11. The composition according to any one of claims 1 to 10, wherein R in the formula is a butyl group. 12. The composition according to claim 11, wherein R ¹ in formula 12 is a secondary or tertiary butyl group. 13. Any of claims 1 to 12, wherein the compound of group (v) is a free alcohol of the formula, or an alkali metal salt, alkaline earth metal salt, ammonium salt, amine salt or ester thereof. The composition described in. 14. The composition of claim 13, wherein the compound of group (v) is a free alcohol of formula or an acetate thereof. 15 Also contains one or more carriers,
A composition according to any one of claims 1 to 14.