JPS60132928A - Diphenyl ether herbicide composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to herbicidal compositions and weeding methods for controlling undesired plant growth, and compounds used in these compositions and weeding methods.

U.S. Pat. No. 41,33'75 discloses the use of certain substituted phenoxy phthalates as herbicides, and also describes the corresponding phenoxy heptatalic anhydride. has been done. However, this US patent only discloses that the acid anhydride is a useful intermediate for the production of the phthalate, and that the acid anhydride itself is biologically active. There is no disclosure as to whether it has any activity or not, and there is no description suggesting this.

the aforementioned phenoxyphthalic anhydride, and 3. 'l--
Another phenoxy 7 with substituent fused ring WJH1 in position
It has now been discovered by the present inventor that talic anhydride has excellent herbicidal activity.

Therefore, the present invention provides a method for the general formula [wherein R1 represents a hydrogen atom, a halogen atom (preferably a chlorine atom), an alkyl group or a haloalkyl group (preferably a trifluoromethyl group];
3 may be the same or different groups, each of which independently represents a hydrogen atom, a halogen atom (preferably a chlorine atom), an alkyl group, a haloalkyl group, a nitro group, or a cyano group; A and B are They may be the same or different groups, each of which independently represents 〉c(R4)2, -x
-1:>N represents a divalent group selected from the group consisting of -R52, l>C-X and >SO2, provided that A is -X
- or > When representing SO2, B must be different from A and not represent C=X; each R4 may be the same or different from each other, and a hydrogen atom or represents a halodane atom, or represents an unsubstituted or substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aryl group (preferably phenyl group), aralkyl group, alkaryl group, alkoxy group, cycloalkoxy group, alkenyloxy represents an alkynyloxy group, an alkoxycarbonylalkyl group, an alkylthio group, an acyl group, an acyloxy group, a carboxyl group, an alkoxycarvinyl group or a heterocyclic group, or represents an amino group of the formula NR6R, where R
When 7 of 4 are hydrogen atoms, alkoxy groups or hydrocarbon groups, the other R4s can also represent a hydroxyl group, or both R4s taken together form the formula =
NR6 can also represent an imino group; 5B5 represents a hydrogen atom, a carboxyl group, a hydroxyl group, or an unsubstituted or substituted alkyl group, an alkoxy group, an aralkyl group, an alkoxycarnyl group or an alkoxycarbonylalkyl group or represents an amino group of the formula NR6R; R6 and R7 may be the same or different groups, each of which represents a hydrogen atom, an unsubstituted or substituted alkyl group, an aryl group or an acyl group; Xl in (1) and X in the above substituent represent an oxygen atom or a phosphorus atom] As an active ingredient, a diphenyl ether derivative having the following:
The present invention relates to a herbicidal composition containing the present invention together with a carrier.

The term "acyl group" as used herein means a group derived by removing a hydroxyl group from an organic acid. The organic acid can be carmenic acid (including carbamic acid derivatives) or sulfonic acid. Examples of suitable acyl groups include alkylsulfonyl, alkylcarbamoyl and alkylsulfonyl groups, specific examples of which include acetyl, methylsulfonyl and dimethylcarbamoyl.

The above substituent is an alkyl group, an alkenyl group, or an alkynyl group, or a group containing these groups (64)
obtain. The substituent may be linear or branched and may contain up to 1-/θ (preferably up to 6) carbon atoms. Preferred examples of this substituent include a methyl group, an ethyl group, an allyl group, and a propynyl group. When it is a cycloalkyl substituent or contains a cycloalkyl group, it can be a group of 3 to 10 carbon atoms (preferably s-), a preferred example of which is the cyclohexyl group. can give. If it contains a haloalkyl substituent, the haloalkyl preferably has up to 6 carbon atoms (more preferably up to t), and the halogen atoms therein are preferably fluorine or chlorine atoms. be. Particularly preferred is a trifluoromethyl group.

If it contains an aryl substituent □, the aryl group is preferably a phenyl group. When it includes a heterocyclic group, this group can be a group having, for example, a virol ring, a pyrrolinone ring, a pyridine ring, a male veridine ring, a furan ring or a pirare ring. The above substituents themselves may optionally be further substituted with another substituent i
In the case of It's good. Examples of such substituted groups include halogen atoms (especially chlorine atoms), nitro groups, cyano groups, hydroxyl groups, alkoxyl groups (e.g. methoxy groups).
, an ester group (for example, an alkoxycarvinyl group) is added.

A preferred composition is a composition containing, as an active ingredient therein, a compound of general formula (1) that satisfies the following conditions, that is, X in formula (1) is an oxygen atom; is an oxygen atom, a carboxyl group%C(R4)2 group; one R4 group can be a hydrogen atom, or an alkyl group or an alkoxy group (especially a methyl group or a methoxy group) having up to 100 carbon atoms; , or an aryl group (especially a phenyl group), and the other R groups are a hydrogen atom or a hydrogen atom (especially a sulfur group, an alkyl group having less than 100 carbon atoms (especially a methyl group) , alkoxy groups (in particular methoxy, ethoxy, globoxy groups) having up to ≠ carbon atoms (1ll), these groups optionally contain no logan atoms (
R4 may be substituted with a cycloalkoxy group (especially a cyclohexyloxy group) of jg carbon atoms, a hydroxyl group, or an alkoxy group (especially a methoxy group), or a carbon Alkenyloxy or alkynyloxy groups having up to 6 atoms (especially allyloxy or propynyloxy groups), alkoxycarbonylalkyl groups (especially ethoxycarmenylethoxy groups), alkylthio groups having up to φ carbon atoms (especially methylthio group, propylthio group) ), an alkanoyl group (especially an acetyl group), a pyridyl group, an amino group of the formula NR6R; R6 is a hydrogen atom or an alkyl group (especially a methyl group) having ≠ or less carbon atoms; R7 is an , carbon atom ≠
an alkyl group (in particular a methyl group), a phenyl group (which may optionally be substituted with one or more halogen atoms (in particular a chlorine atom)), an alkylsulfonyl group or an alkylcarbamoyl group, an alkylsulfonyl group Group (
in particular an acetyl group, a dimethylcarbamoyl group or a methylsulfonyl group; B is an oxygen atom or a C(R4)2 group [wherein each R4 group may be the same or different from each other and each independently represents a hydrogen atom, or an alkyl group or alkoxy group (especially a methyl group or a methoxy group) of up to 100 carbon atoms, or N
R5 group, where R5 is a hydrogen atom, or an alkyl group (particularly a methyl group) having up to 100 carbon atoms, a pe/
This is a composition containing a compound that satisfies the condition that it is a zyl group, an alkoxycarbonylalkyl group having not more than a few carbon atoms (% ethoxycarbunylmethyl group or ethoxycarnylethyl group).

A particularly preferred composition is one in which R1 is a trifluoromethyl group, R2 is a halogen atom (especially a chlorine atom),
This is a composition containing a compound of formula (1) in which R is a hydrogen atom as an active ingredient.

With seven exceptions, the compounds of formula (1) are new compounds. That is, this new compound has the symbols A, B,
R,, R2, R3, R4, R5, R6 and R7 are the diphenyl ether derivatives of formula (1) having the meanings previously described, but the only exception is the compound "-(,2-chloro-≠ -trifluoromethylphenoxy)-phthalic anhydride" is a compound known per se.

As will be readily appreciated, in compounds where asymmetric carbon atoms are present as a result of the introduction of substituents, stereoisomers will exist. It is also possible (11) to obtain a compound in which tautomers exist by introducing a plurality of polarizing substituents. All of these various compounds and mixtures thereof, as well as herbicidal compositions containing such isomers and mixtures thereof as active ingredients, are within the scope of the present invention.

Furthermore, the present invention provides a method for producing a novel diphenyl ether as defined above, comprising: a phthalide of the following formula;
The following formula [In these formulas, A%B%X%B, R2 and R3 have the above-mentioned meanings, and one of 2 and Q has a halodane atom (preferably a chlorine atom) or a nitro group and the other one is the formula -0M
and M represents a hydrogen atom or an alkali metal atom.

In a preferred embodiment of this process, a compound of formula (n) in which Q is a hydroxyl group is reacted with an alkali metal hydroxide in a gold alkanol solvent (e.g. ethanol solvent), thereby producing the corresponding alkali metal salt. let me,
Next, this alkali metal salt is reacted with the compound of formula (1) (in which 2 is a chlorine atom). The reaction of the alkali metal salt with the chloro compound of formula (III) is carried out in a suitable organic solvent (e.g. dimethylsulfoxide, sulfolane, dimethylformamide or dimethylacetamide) at a relatively high temperature (e.g. above 23°C, It is preferred to carry out the reaction at a temperature between ≠θ° C. and the reflux temperature), and more preferably the reaction is carried out under reflux in an inert atmosphere such as nitrogen.

A compound in which X in formula (1) is sulfur can be produced by reacting a corresponding compound where X=O with phosphorus pentasulfide. Compounds in which A in formula (1) is a haromethylene group are advantageously produced by reacting the corresponding methylene compound with a suitable halodanizing agent. For example, a compound in which A in formula (1) is a CUB r group can be produced by reacting the corresponding compound where A=)CH2 with N-promo succinimide; 1 is carried out in the presence of a peroxide such as and in a solvent such as carbon tetrachloride! Delicious. A compound in which A in formula (1) is a hydroxymethylene group can be produced by hydrolysis of the corresponding no-romethylene compound.

Both X and B in formula (1) are oxygen atoms, A is C(R4) 2 groups, seven of R4 are hydrogen atoms, and the other seven R4 are already described A compound having any of the groups (excluding hydrogen and hydroxyl group) is the corresponding compound of A=CH(OH) and the compound of the formula HR4 [here, 84 has the same meaning as in the case of formula (1)]. have (
However, in the case of manufacturing a compound in which R4 is a carboxylic acyloxy group, in place of the compound of the latter formula) IR4, a compound of the formula A( +20 (where Ac is an alkylcarnyl group). This reaction is advantageously carried out under reflux of the reaction mixture. In some cases, It is advantageous to use an excess of the reactant R4 so that it also serves as a solvent for the reaction.

In the case of pure substances, it may be convenient to dissolve the reactant HR4t in an organic solvent (eg acetonitrile or methyl ethyl ketone) and use it in solution.

It has been found that the compound of general formula (1) has good herbicidal activity. The present invention therefore relates to the use of a compound of chocolate (1), or a composition containing it, as a herbicide. Furthermore, the present invention also provides a method for controlling undesired plants at a growing site by treating the site with the above compound or composition. Application of the above-mentioned compounds or compositions to the growing site may be pre-emergent or post-emergent. The amount of this active ingredient used is, for example, O, OS
−'≠ may be 9/ha and 1. □The carrier blended into the composition according to the present invention is
This can be done with any material that can facilitate the storage, transport or handling of the active ingredient, including for example explants, poles or soil, etc.). The carrier may be solid or liquid. Also, substances which are usually gases but which can be liquefied upon compression can also be used.6 Any carrier commonly used for the preparation of herbicidal compositions can also be used in the present invention. The compositions of the present invention preferably contain 0.0% of the active ingredient. Contains j-9j weight ratio.

Examples of suitable solid supports include natural and synthetic silicates and silicates, including natural silicas such as diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as athanoglugite and vermiculite; aluminum silicates, such as kaoli night, montmorillonite and pyrite; calcium carbonate,
Calcium sulfate; ammonium sulfate; synthetic silicon oxide aquariums; synthetic calcium or aluminum silicates; elemental substances such as carbon and sulfur; natural and synthetic resins such as coumaron resins, polyvinyl chloride, styrene polymers and copolymers; solid/+7 chlorophenols; Bichupa - Men; Wax; Solid fertilizers such as superphosphates.

Examples of suitable liquid carriers include: water; alcohols such as Improno J? Nol, glycol:
Ketones such as acetone, methyl ethyl ketone, methyl isodity ketone, cyclohexanone; ethers; aromatic or aromatic-aliphatic hydrocarbons such as benzene, toluene, xylene; petroleum fractions such as kerosene, light mineral oils; chlorinated hydrocarbons such as carbon tetrachloride , perchlorethylene, trichloroethane. Mixtures of various liquids are also generally suitable.

Pesticide compositions are generally formulated and transported in the form of concentrates, immediately after which they are diluted and applied by the applicator. By presence of a small amount of the carrier, which is a surfactant, the p1 dilution operation can be carried out more easily and quickly.

Therefore, in the composition of the present invention, it is preferred that at least one of the carriers is a surfactant. For example, the composition may contain at least two carriers, at least one of which is a surfactant.

The surfactant can be an emulsifying agent, a dispersing agent or a wetting agent. This can be nonionic or anionic to obtain IC. Examples of suitable surfactants include sodium or calcium salts of polyacrylic acid and ligninsulfonic acid;
Condensates of fatty acids or aliphatic amines or amides containing at least 72 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; glycerol, nrubitan, sacrose or pentaerys IJ
) - fatty acid esters; condensates of the above with ethylene oxide and/or zolopylene oxide; condensations of fatty alcohols or alkylphenols (e.g. p-octylphenol or p-octylcresol) with ethylene oxide and/or propylene oxide. sulfated products and sulfonated products of these condensates; alkali metal salts or alkaline earth metal salts of sulfuric acid esters or sulfonic acid esters containing at least 70 carbon atoms in the molecule, preferably sodium salts [for example, sodium lauryl sulfate, Mention may be made of sodium secondary alkyl sulfates, sodium salts of sulfonated castor oil, sodium alkylarylsulfonates (eg, sodium dodecylbenzenesulfonate), polymers of ethylene oxide, and copolymers of ethylene oxide and zolopyrene oxide.

The compositions of the invention can be prepared in the form of formulations such as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, concentrated suspensions or aerosols.

Wettable powders generally contain t, 2J-1,5oqb or 76% C of the active ingredient (by weight), which, in addition to an inert solid carrier, contains 3-10% by weight of a dispersant and optionally a stabilizer, and It may contain 0-10% by weight of/or other additives such as penetrants or adhesives (5tLeker). Dusts are generally prepared in the form of dust concentrates having a composition similar to that of wettable powders, but without the inclusion of dispersants. This is further diluted with a solid carrier in the field to give a composition which generally contains 2-/0% by weight of active ingredient and is applied.

Granules are generally 1o-iooBs mesh (/, Otsu 7 Otsu-
0,/j2M), which can thus be produced using agglomeration or impregnation techniques. Generally, granules contain active ingredients ///2-75% by weight.
and 0-10% by weight of additives (eg stabilizers, surfactants, modifiers for sustained release, and binders).

So-called free-flowing dry powders consist of relatively small granules containing a relatively high concentration of active ingredient.

Emulsifiable concentrates generally contain a solvent and, if necessary, a co-solvent, and in addition 10-30% w/v of active ingredient, no emulsifier or 20% w/v and other additives. (e.g. stabilizers, penetrants and/or corrosion inhibitors) in an amount of 0-20 wt. Suspension concentrates are non-sedimenting, stable, flowable products that generally contain 10-75% of the active ingredient.
% by weight, dispersant o, 5-is weight %, suspending agent (e.g. protective colloid or chicktroping agent) 0. /-1
0% by weight and other additives (e.g. antifoams, corrosion inhibitors, stabilizers, penetrants and adhesives > o-io weight%) and water or organic liquids (provided that the organic liquids contain substantially no active ingredients). Polarizing organic solids or inorganic salts may also be present in the composition to increase anti-settling properties or to prevent water from freezing. can.

Aqueous dispersions and emulsions, such as those obtained by diluting the wettable powders or emulsifiable concentrates of the invention with water, are also within the scope of the invention. Such dispersions or emulsions may be water-in-oil or oil-in-water, and may have the consistency of thick mayonnaise.

The compositions of the invention may also contain other ingredients, such as one or more compounds with herbicidal, insecticidal or fungicidal activity.

EXAMPLES In order to more specifically illustrate the present invention, Examples are shown below.

Example 1 3-(2'-chloro-≠-trifluoromethylphenoxy)phthalidej-hydroxyphthalide(yo31/>'tethanol(
Potassium hydroxide (,2,5,9
) was added and the solution was refluxed for 3 hours. The solvent was removed, the L1 residue was dissolved in dimethyl sulfoxide (!rOWLl), and 3.11-dichlorobensitrifluoride C1,21> was added. Stirred at 760° C./♂ hour in dry nitrogen, then it was cooled, poured into water, neutralized with dilute hydrochloric acid and the product was extracted with methylene chloride. Desired product with melting point 10 T///C. was gotten.

Analysis value calculated value (as C, 5H805C1F) C5-44
Do H2,≠CH Measured value CJI/-, 1H,2,j-CH Example 1 s-<, z'-chloro-ψ-trifluoromethylfu)
Benzoyl peroxide in the form of a small islet was added. The reaction mixture was stirred and refluxed under strong light. Ko·
- Phosphoric acid imide began to precipitate. The reaction mixture was cooled, filtered, washed with carbon tetrachloride, and the solvent was removed. Chromatographic separation (silica column; eluent methylene chloride) gave the desired product in the form of a pale bluish-orange viscous oil.

Analysis value calculated value (as C, 5H7CtBrF, O,) Cll
1A2 11/, 7'16 measurement value C1AlA2 H/
,'Z% Example 3! ;-<2'-1o rho≠'-trifluoromethylphenoxy)=l-thiophthalide Example/Product <i, zsi> and phosphorus pentasulfide (,2,,2,
9) and dioxane (/jmJ) dried with sodium.
) and refluxed for 1 hour while stirring. The reaction mixture was cooled, filtered, dried, washed with methylene chloride and purified by chromatography. The desired product was obtained in the form of a pale blue-yellow solid with a melting point of r6-et<0>C.

Analysis value calculated value (C,, H8CtO2SF, Toshi-C) C32
,,2H13 Measured value C3I, 1 H2, 3 Example HiroN-benzyl-5(2'-nitro-trifluoro-tetramethylphenoxy)phthalimide N-benzyl-j-hydroxyphthalimide (o, Dohirog) and water Potassium oxide CO, IP&') was dissolved in ethanol (jom) and the solvent was evaporated. The residue was dissolved in dimethyl sulfoxide (30 ml) and diluted with Hiro-chloro-3-nitro-pencitrifluoride (0,731
) was added. This mixture was heated to /♂0℃ for 6 hours,
Pour it into the water.

The mixture was extracted with ethyl acetate and the ethyl acetate layer was separated: dried and evaporated. The desired product was obtained in the form of pale blue-yellow crystals. This oil was precipitated from ethanol to give pale blue-yellow columnar crystals. Melting point/A&-/&7°C.

Analysis value calculated value (as C22H15F5N205) cj9.
7H, 2, Ta N Otsu, 3 measurement value Cj'? JH3,0
H4,,gExample N-benzyl-5-(,2'-chloro-≠'-trifluoromethylphenoxy)phthalimide≠-chloro-3-
3. In place of nitropenzotrifluoride. The same procedure as in Example ≠ was carried out, except that ≠-dichlorobensitrifluoride was used. The desired product has a melting point //
It was obtained in the form of a white solid with a temperature of -2/°C.

Analysis value calculation value (as C22H1,F, C1NO3) Cl,
/, 2) 13.0 N3.2jchi measurement value C6/, 2
H2, riN3. /q6 Example 6 3-(2'-10rho≠'-trifluoromethylphenoxy)-3-hydroxyphthalide The product of Example 2 was mixed with 20 vtl of water and refluxed for 3 days.
The reaction mixture was subjected to an extraction operation using methylene chloride,
It was then dried. By removing the solvent and performing a chromatographic purification operation, the desired product with a melting point of /1-3-/≠7°C was obtained @calculated analytical value (as C15H804CtF) C32,2
N2.3% measurement value C,5-/, ta H,2,ll-chi Example 7! ;-<2'-/Rolow≠'-trifluoromethylphenoxy)-3-methoxy-phthalide (a)! ;-Hydroxyphthalimide (yo5O) dissolved in ethanol (jOm) and potassium hydroxide (,2,
si> was added and the solution was refluxed for 3 hours.

The solvent was removed and the residue was dissolved in dimethyl sulfoxide (jOm
) and added 3.11-dichloropene citrifluoride (J', 2&). The mixture was stirred for 11 hours at 760° C. under dry nitrogen, then it was cooled, poured into water, neutralized with dilute hydrochloric acid and the desired product CA) was dissolved in methylene chloride (25 ml). , benzoyl peroxide in small pellet form was added. The reaction mixture was refluxed under strong light with stirring. Succinimide began to precipitate. The kernel mixture was cooled, filtered, washed with carbon tetrachloride, and the solvent was removed. Chromatographic separation (silica column; eluent methylene chloride) gave the desired product (B) as a bluish-orange viscous oil.

(c) The above product (B)' was combined with 20 ml of water and refluxed for 3 days, and the reaction mixture was extracted with methylene chloride and dried. By removing the solvent and performing a chromatographic purification operation, the melting point/1A3
-/≠7°C t -(2'-chloro-≠'-trifluoromethyl-phenoxy)-3-hydroxyphthalide was obtained. This product (C'l is Example g-io below)
``Hydroxyphthalide 1''.

(d) Hydroxyphthalimide (/, Hiro, 1) produced through the above steps (4)-(C) was mixed with methanol (, 29
m1) and refluxed for 1 hour while stirring. The residual solvent was removed by evaporation and the product was purified by chromatography. The chromatographic run was carried out on a silica column and using methylene chloride as the eluent. The product was obtained as a clear oil which was recrystallized to give the desired product as crystals with a melting point of 67°C.

Analysis value calculated value (as C14H10CtF304) Cj3. B; N2. I; C15', Tachi measurement value Cj3.1
．． ', H2, Ri: C19, Example: -(,2'-chloro-≠'-trifluoromethylphenoxy)-3-acetoxyphthalide Hydroxyphthalide (0,7E/) was dissolved in acetic anhydride (10 d
) and refluxed for 5 hours with stirring. Excess acetic anhydride was removed by evaporation, the residue was washed with saturated sodium bicarbonate solution, extracted with methylene dichloride, the organic phase was washed with tX carbonate solution and dried over sodium sulfate. The solvent was removed and the product was purified by chromatography and recrystallized. A solid product was obtained with a melting point of l/3°C.

Analysis value calculation value (as C17H1°CtF, 05) Cj”,
2. D; H, 2, 6 measurement value Cj3.0', N2.7
Person in charge Ta! -(2'-/Roreau≠'-trifluoromethylphenoxy) -j -N',N'-Dimethylureidophthalidopanodimethylurea C0,211> solution (solvent is methyl ethyl ketone λoynt> and hydroxyphthalide (
(7,711) was added and the mixture was refluxed for 2 hours.
Then, an additional 0.2 g of the urea compound was added. After refluxing for a further 6 hours, the solvent was removed and the residue was suspended in water, shaken to remove unreacted urea, taken up in ethyl acetate and purified by chromatography. A mouse product was obtained in the form of a solid with a melting point of ljμ°C.

Analysis value calculated value (as C18H44N2O4CLF5) C50
, 7; Hj, 44: NA7chi measurement value Cjyu 0", H3
, 2; Nt, Hirochi Example 10 j-(2'-/Rolow≠'=) IJ fluoromethylphenoxy)-3-3,≠-dichloroanilinophthalide 3.1I--dichloroaniline (o, si> Hydroxyphthalide was added to a solution in dry acetonitrile (7117) and then crystals of p-toluenesulfonic acid were added. The mixture was refluxed under stirring for 55 hours and the solvent was removed. The residue was purified by clotgelaf operation. The product was obtained in the form of a solid with a melting point of 1 g/g°C.

Analysis value calculation value (as 11NQ5Ct!F5 for C21) (J/
, A:u, 2.2; N2. Measured value C31,ly;
)N2. I; N near example/l-≠O A number of compounds were produced by a method similar to that described in the above example, but their compositions, analytical values, properties, etc.
Shown in the table. In all cases, the composition and structure of the resulting compounds were confirmed by n, m, r analysis. The symbols "'m, m, *," in the table mean that the truth of the empirical formula has been confirmed by mass measurement. The composition of these compounds is based on the substituents in the formula below. Rz *
Indicated by A and B.

Example 1/L/ Herbicidal Activity In order to investigate the herbicidal activity of the compound of the present invention, tests were conducted using the following plants as representative examples of plants. That is, the test plant was corn (Zea mayi) (Mz);
Rice (Oryza 5atlva) (R); Wildflower (Eahinochloa eruagalli)
(BG) ; Oat wheat (Av*na 5at
iva) (0): Amateur (Li num uslt)
atigsimum) (L); Mustard (5inaps)
ls alba) (M) ;bee) (Bet
a vulgaris) (SB): Dice (G
lycinemax) (S).

Two types of tests were conducted: a pre-emergence test and a post-emergence test. In the pre-germination test, a liquid composition containing the compound was sprayed before germination onto the soil of the land where the seeds of the above-mentioned plants had been sown some time before the composition was sprayed. Two types of post-emergence tests were conducted: a soil trench test and a foliar spray test. In the soil trench test, a liquid composition containing the compound of the invention was applied to the soil of the land where the seedlings of the plants were growing (drenching). In the foliar spray test, seedlings were sprayed with a liquid composition as described above.

The soil used in this test was a prepared horticultural loam.

The composition used in this test was “Triton-x −/
! ;! ” (registered trademark), an alkylphenol/ethylene oxide condensate commercially available as O
It was prepared from a solution of the test compound dissolved in acetone containing 1% by weight.

That is, this acetone solution is diluted with water and the composition thus obtained is combined with the active compound sh or /kl? /ha, but the capacity is 1,001/ha.
(for soil spray tests and foliar spray tests): or at an application rate equivalent to 10 to 9 ha of active compound, but with a volume of approx.
0001/ha (for soil trench tests).

In the pre-emergence test, untreated soil from the plotted land was used as a control sample, and in the post-emergence test, untreated soil from the site where the seedlings were growing was used as a control sample.

72 days after spraying on the leaves and soil, or 73 days after drenching the soil, the condition of the test plants was visually observed to evaluate the herbicidal effect of the test compound. It was described using a rating scale. A grade of "O#" means that the plants grew as in the untreated control sample, and a grade of 1 means that the plants died. A difference of one grade on the rating scale means a difference in effectiveness of about 10 degrees.

The results of this test are shown in Table 2. In Table 1, individual compounds are indicated by example (preparation) number (ie, compound number).

Below margin

Claims (1)

[Claims] (1) General formula [wherein R1 represents a hydrogen atom, a halogen atom, an alkyl group, or a haloalkyl group, R2 and R6 may be the same or different groups, and each of them is independently represents a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, a nitro group, or a cyano group, A and B may be the same or different groups, each of which independently represents >C(R4 )2, -x-1
represents a divalent group selected from the group consisting of >N-R5, )C-X and >S0□, provided that A is -X- or >8
02, B must be different from A and not represent ', c-X; each 84 may be the same or different from each other and may not represent a hydrogen atom or a halogen atom. Represented by an unsubstituted or substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aryl group, aralkyl group, alkaryl group, alkoxy group, cycloalkif group, alkenyloxy group, alkynyloxy group, alkoxylic d? Nyl alkoxy group, alkylthio group, acyl group, acyloxy group, carboxyl group, alkoxycar represents a nyl group or a heterocyclic group, or represents an amino group of the formula NR6R, provided that seven of R4 are hydrogen atoms, an alkoxy group or When a hydrocarbon group, the other R4 can also represent a hydroxyl group, or both R4 together can represent an imino group of formula =NR6;
R5 represents a hydrogen atom, a carboxyl group, a hydroxyl group, or an unsubstituted or substituted alkyl group, an alkoxy group, an aralkyl group, an alkoxyl group, or an alkyl group. represents a nyl group or an alkoxycarbonylalkyl group, or has the formula NR
6R, represents an amino group; R6 and R7 may be the same or different groups, each of which represents a hydrogen atom, an unsubstituted or substituted alkyl group, an aryl group or an acyl group; X, and X in the above substituents represents an oxygen atom or a sulfur atom] as an active ingredient,
A herbicidal composition comprising t% of a carrier. (2) The active ingredient is a compound having the general formula (1), where X is an oxygen atom, and A is an oxygen atom, a carmenyl group, and two C(R4) groups. is a hydrogen atom υ, or an alkyl or alkoxy group with ≠ carbon atoms sb, or an aryl group, and the other seven R4 are hydrogen atoms, halogen atoms, or hydroxyl groups, or carbon Alkyl groups with up to 6 atoms, alkoxy groups with up to ≠ carbon atoms (optionally substituted with halogen atoms, hydroxyl groups or alkoxy groups), cycloalkoxy groups with j-1 carbon atoms, carbon atoms 6 or less alkenyloxy groups or alkynyloxy groups, alkoxycarbonylalkoxy groups,
An alkylthio group of up to 5 carbon atoms, hb, or an alkanoyl group, a pyrinol group, or of the formula NR6R. R6 is a hydrogen atom, or an alkyl group having not more than ≠ carbon atoms. B is an alkyl group having not more than ≠ carbon atoms, or an unsubstituted or substituted phenyl group (this substituted phenyl group is substituted with 7 or more halogen atoms), or an alkyl group Cal is a nyl group, an alkylcarbamoyl group, or an alkylsulfonyl group; B is an oxygen atom; ,
Each independently represents a hydrogen atom, or t
R5 is a hydrogen atom, or an alkyl group with ≠ carbon atoms, or a benzyl group; 2. The composition according to claim 1, wherein the alkoxylic acid or the alkoxylical group having up to g carbon atoms is a nyl alkyl group. (3), B is an oxygen atom and Si is C(R4)2 group (
(4) R is a trifluoromethyl group; The composition according to claim 1, 2 or 3, wherein R2 is a halodane atom, and R2 is a hydrogen atom. (5) At least two types of carriers Contains, of which? The composition according to any one of claims 7 to 5, characterized in that at least/pole is a surfactant. (6) In the Q diphenyl ether derivative of formula (1), the substituent thereof is the same as described in claim 1, provided that ≠-(2-chloro-≠-trifluoromethylphenoxy) The diphenyl ether derivative according to item 1 of the patent application, characterized in that it does not contain phthalic anhydride. (7) The diphenyl ether according to claim 6, which is a diphenyl ether of formula (1) having a substituent defined in any of claims λ to j. . ,,(8), In the method for producing diphenyl ether according to claim 6, the following formula (in these formulas, A%B, X%R4, R2 and R3 are as defined in claim 6 seven of 2 and Q represent a halogen atom or a nitro group, the other l represents a group of formula -0M, and M represents a hydrogen atom or an alkali metal atom). and, if the formation of thio7thallide is desired, followed by a reaction with phosphorus pentasulfide, or if the desired compound has a halo or hydroxymethylene group, A method for producing diphenyl ether, which comprises subsequently reacting with a halodating agent, and, in the case of producing a hydroxymethylene derivative, hydrolyzing the halomethylene conductor obtained as described above. (9) The first reaction is carried out by the formula (n
) and an alkali metal hydroxide in an alkanol solvent, and the resulting alkoxide compound is then converted into a compound of the formula (where 2 is a chlorine atom) (
The manufacturing method according to claim g, which comprises reacting with the compound of [1]. 3. The method for producing diphenyl ether according to claim 2, wherein the reaction between the α1 alkoxide and the chloro compound (III) is carried out in an organic solvent at high temperature under an inert atmosphere. R9 characterized in that the growing site is treated with a composition according to any one of claims 1 to 5 or a compound according to claims 6 or 7. , a method for controlling undesirable plants in their natural habitat. (b) Use of the diphenyl ether according to any one of claims 1 to 7 as a herbicide.