JPS5838241A - Benzamide derivative and herbicide containing the same - 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 a sII# constant O benzoic acid adeno-adductor and a herbicide containing the same.

The inventors of the present invention focused on the herbicidal activity of compounds of the benzoin group, and discovered the unique action of a specific benzoin-inhibitor, which led to the completion of the present invention. Ta.

The 10th invention of the present invention is based on the -dake formula [wherein ORI and bird represent a hydrogen atom, a lower alkyl group, an ffi & alkenyl group, a lower alk; A pyrrolidine ring may be formed between and. ] and is a benzoic acid amide ll conductor. The second invention is a herbicide containing the compound.

Next, representative examples of the Ki-benzo-acid aado derivatives of the present invention will be shown.

The compound of the present invention can be synthesized by the various methods shown below.

(1) A 2-halomethyljujumerine compound subtracted by the general formula [wherein, Commuting. ] and react with 11g4 of metahydrobenzoic acid oxide.

That is, 2++ AW methylnatamines [1] meta-hydroxybenzoic acid dielectric a conductor [seal] and a wheezing solution m or in an inert organic solvent, l! ＾When heated in the presence of an atomizing agent, it reacts more with K. Suitable solvents include toluene, xylene, dimethyl fluoride, dimethyl sulfonate, Zig9, etc., or mixtures thereof. Reaction temperature and reaction time are as follows:
It varies depending on the type of chestnut that is mainly used, but
Generally, a temperature of 50° C., 1% A, and a high flow rate of 1 to 10 hours is suitable. [After completion of the reaction, the target compound can be obtained from the reaction mixture according to conventional methods.

(Amount) Methanalatyl methoxybenzoic acid expressed by the general formula t or so O! The L-responsive body is reacted with the general formula [1 [However, in the formula, FL%%- is defined as leaving work as defined in W] and is expressed by the general formula [1].

H The reactive derivatives referred to here are acid^lides.
* Examples include anhydrous substances or esters.

-Summary- This reaction is carried out without a groove or in an inert organic S medium. Among free acid and reactive W conductors, it is common to use swI and M rides), l! Performed in the presence of a chlorinated agent, the MKIk 9-acid chloride is synthesized by the free acid and thiol chloride or phosgene. Inert organic compounds include toluene, xylene, and diethyl ether.

Tetotsuhydrofuran, dioxane, t) cool methane,
Suitable dechlorinated water bulking agents include carbon tetrachloride, ethyl acetate, and their depleted substances.

For example, triethylteine, carbonated water, sodium chloride, etc. Mu.

O uses sodium carbonate, etc.! That's 1 win.

The reaction is generally carried out at -111 to 51 temperature and under cooling. ! The L response time varies depending on the main KIL response temperature and the compound used, but it ranges from instantaneous to several hours. ! After the reaction is completed, the target material can be extracted from the reaction mixture according to a conventional method.

Next, an alternative synthesis example will be shown.

Synthesis example 1 N-ethyl ink-(2-naphthylmethoxy)
N-ethyl benzoate 5-human-xybenzoate tsr,z
-P11 chillnaphthalene 2.2f, carbonic acid lrim 17F
Dissolved in dimethylformamide 10-#C, 1OaCK
and stir for 1 hour! After finishing the L response, [100 responses]
The precipitated crystals were filtered and dried to obtain crude crystals 50F.

6. Recrystallize this mixture of toluene and petroleum ether #1 #l. 2.4 t of N-methyk 1-(2-naphthylmethoxy)benzoic acid ζad was obtained. Melting point 129~1!1
1℃ Yield 7 & 7 1I421 N41$? Experimental value: C7 & i4 H418N44δIR (N Tsuru Jo
1 method, II large absorption es-') 5240 1610
1850 1ffi4B Synthesis Example 2 N-Allyl
Sumi-(2-naphthylmethoxy)benzoic acid ado Sumi-(2-su7thylmethoxy)benzoic acid yi ■ride ho
To the tetrad W7 solution of t, stir while cooling in an ice bath.
While I was at it, I added Aryluaan i- dropwise.

After the dropwise addition was completed, the mixture was stirred in chamber 11 for 30 minutes. After the reaction is complete.

Pour the reaction solution into 20 rows of water.1. The precipitated crystals are filtered and dried to obtain crude crystals L! I got f. Recrystallize this from the toluene ligroin back room #1m.

N-allyl sumi-(2-su7thylmethoxy)benzoic acid aodide 2.1f was obtained. One point 98~100℃ yield 6&2%
(#Riman Twid group jm) To elemental analysis value C□, calculated value as NO3 5c79.5D H5,9? N, 442 Experimental value: C7? , 13 Hl48 H4,5? IR
(NuJol method, II large absorption am-') 5220
1620 1170 1240 Synthesis example 5 N
, N-tetramethylene ink-(2-s7tylmethoxy)
Benzoic acid Arado N, N-tetramethyl y s-t V Benzoic acid ryondo lHt, 2-P IU Tilnaphthalene 46f, Calicum carbonate 5. Dissolve Of in dimethylformamide and stir for 1 hour at 100°C. After the reaction is complete, pour the reaction bulk material into 500sgo of water and filter the precipitated crystals.
J, dried to obtain 9-9.8t of crude crystals. This was recrystallized from ethanol/water Oa solvent to obtain N,N-tetotsumethylene ν 3-(2-su7
Chirmetokki &) Benzoic acid (dochi7ft 11*61k
j [14N ~ 14 l C yield 77.8 N (pw4
Methyl body basis) Elemental analysis value CHH□No, as r R (Ntsjol method maximum absorption iゝ) 1410
1B'? 4 1410 1248 The herbicide of the present invention contains a compound represented by the general formula [1] as an active ingredient and is combined with a carrier.

It can be obtained from Tok to prepare formulations in the form of wettable powders, emulsions, powders, granules, etc. Among the carriers, a commonly used organic solvent is used as a liquid carrier, and a commonly used mineral fine powder is used as a Li1 carrier. When preparing a formulation, a surfactant can be added to impart emulsifying properties, dispersibility, spreading properties, etc.

For use as a herbicide, k is the active ingredient compound 10- Apply the product sufficiently to achieve the desired herbicidal effect.

The amount applied is within the range of 11 to 2000F/101 of the active ingredient, but in the past, R was 11 to 1000F/10.
1, and preferably 1001%/-&L50Of/
A hydrating agent that has good lea and combines active ingredients (L1 & Ishi 5ON).

It is used in O-type 111kll formulations such as emulsions and powders.

With emulsion! IKFi, the active ingredient is dissolved in an agriculturally acceptable organic solution* and a solvent-soluble emulsifier is added.

Suitable i11 media are generally water immiscible.

Hydrocarbons, chlorinated elements, ketones, esters.

Alcohols, amides, etc. are welcome.

Useful e-solvents may include toluene, xylene, salt, perchlorethylene, cycloethylene, isophorone and dimethylformamide, and mixtures thereof. Particularly suitable solvents are ff general hydrocarbons and keto y@, but a mixture of old Haruka Fi solvents is used.

The surfactant used as an emulsifier accounts for about 5 to 20 parts by weight of the emulsion and may be anionic, cationic, or nonionic.

Anionic surfactants such as IL-alcoholic acid or sulfonate, furkyl teryl sulfonate or sulfonate/cynate 1, such as calcium dodecylbenzene sulfonate or sodium dioctyl sulfosuccinate.

Cationic surfactants 1 include aliphatic alkyl diene salts and fatty acid alkyl quaternary salts 1, for example, tucryl gamma chloride hydrochloride or lauryl dimethylpenzyl chloride.

Nonionic emulsifiers that may be used include esters, phenolics, fatty acids, mercaptans or fatty acid ethylene oxide adducts, such as polyethylene esters of stearic acid or ethylene oxide adducts. Polyethylene of octylphenol with a seal 9
=r-ether.

The concentration of the active ingredient is 51 to 80 parts by weight, @KIO
A suitable amount of SS is 30 to 30 parts by weight.

Wettable powders are prepared by adding the active ingredient to an inert micronized surrounding carrier and a surfactant. The active ingredient is present in the range of 51 to 50 parts by weight, and the surfactant is present in the range of 20 to 20 parts by weight.

The solid carriers used for combination with the active ingredient are naturally occurring clays, silicates and carbonates, and organic carriers. Typical examples of these are kaolin, gicrite, and aller's earth.

Merck, diatomaceous earth! Danesium lime, mud! and walnut flour.

Commonly used emulsifiers and filtering agents include polio IP1/ethylated alkylphenols, i*i alcohol fatty acids and alkylamanes, alkylaryl sulfonates and dialkyl sulfonuccinates.

Spreading agents include materials such as glycerol nitrate and a conjugate of oleic acid and polyglycerin modified with 7-talic anhydride.

The dispersant is anhydrous! For example, a copolymer of leic acid and diisobutylene, sodium chloride salt, sodium geninsulfonate, and phorpentaldehyde donutarin salt, etc. are used. ! - Leak.

The active ingredient in the powder is 0111mKtJ! It is particularly effective when combined with an inert carrier such as Tal I, finely divided clay, diatomaceous earth, magnesium carbonate or wheat flour.

The active ingredient is present in the range of 10&tnL80 parts by weight, so the concentrated powder can be used as a herbicide, but when applied as a herbicide, it is diluted to about 11 to 20 parts by weight by adding more solids.

Granule #'i, when the active ingredient is incorporated into an agriculturally acceptable carrier such as bentonite, kaolin clay, or diatomaceous clay, such granules contain 1 to 50 parts by weight of the active ingredient. include.

The herbicide of the present invention can be applied to grasses known to be harmful to paddy fields, such as B. novitrium and cylindrical grass. It's one of the most popular! ! i
It also shows herbicidal activity against callifolia.

Chemical damage to rice is unacceptable to society.

Next, the herbicide of the present invention will be explained using formulation examples and test examples.

14- Specific examples for the preparation of the present invention agent are shown below.
tashi "parts" Saa TameOFi means "parts by weight".

Example 1 (emulsion) Compound number - 125 parts Xylene 85 parts xanon to siku a go part 7 ball 800A 10g (Toho actinic radiation trademark) were mixed and dissolved uniformly to obtain an emulsion of the present invention.

Example 2 (hydrating agent) Compound number - 250 parts Kaolin clay 45 parts Crane pole 50! ?　　　　　　5 parts were mixed and ground to obtain a wettable powder of the present invention.

Example 3 (powder) Compound book q-s　　　　s part Kaolin clay 95 parts The mixture was mixed and ground to obtain a powder of the present invention.

Implementation Ip44 (Granules) Chemical compound number - 75 parts Bentonite 45 parts Tal / 45 parts V / Ingredients Sulfone Shun Soda 5 parts are homogeneously ground - Kl 1 mixture, water is added and kneaded, granulated and dried to produce the granules of the present invention Obtain *.

Next, the usefulness of the compounds according to the present invention will be specifically explained in the following test examples.

Test example (Paddy soil treatment m) A bot with a diameter of 1t5a + * depth of 10a + is filled with paddy soil! ! After adding rice field soil containing various rice field weeds to the sandals,
Overflowing after fertilizing for 1 generation! Two paddy rice seedlings (variety: Ehonpare, Il 2.5 harvest) were transplanted. After transplanting paddy rice 4
A predetermined amount of the rainwater dilution solution of the present invention was dropped into the water using a pipette on a daily basis.

Investigations were conducted on the 20th day after chemical treatment to determine the herbicidal effect and the presence or absence of nest marks on paddy rice using II*. The results are shown in Table 2. Evaluations in Table 1 are based on the following criteria.

Weeding effect index Qinshu index 5 = Complete weeding effect -1 Wushu 4:80 ~ Weeding effect of FOX
±1 small book 5: weeding effect of 60-79N static: small book 2 wealth 40-159X weeding effect 8 large buttocks 1! 2O-
59X herbicidal effect l 1! Jinsho o: 2ON Q lower 2) 51 ml X t LIE17- Second Table 18-

Claims (1)

[Scope of Claims] 1. General formula [wherein H and H in the formula are hydrogen atoms, lower alkyl x groups,
A benzoic acid and derivative represented by a lower alkenyl group, a lower alkoxyalkyl group, and R1 and R1 may form a pyrrolidine ring together with the ms atom in the formula.2 General formula [However, He and A in the formula represent a water IA atom, a lower furkyl group, a lower alkenyl group, a lower alkyl group; A corner herbicide containing a benzoic acid tedendo derivative represented by ].