JPS5899443A - Benzamide derivative and herbicide containing the same - Google Patents

Abstract

NEW MATERIAL:A benzamide derivative of formulaI[R1, R2 are H, lower alkyl, lower alkenyl, lower alkinyl, lower alkoxy, lower alkoxyalkyl, lower haloalkyl, R1 and R2 may incoporate with N in the formula to form a saturated heterocyclic ring (one of C-atoms may be replaced with an oxygen atom)]. EXAMPLE:N,N-dimethyl 3-(1-naphthylmethoxy)benzamide. USE:A herbicide, which shows herbicidal effect against barnny yard grass, smaller flower unbrella plant and water wort, known as strong weeds in rice plant fields but gives no chemical injury to rice plant. PREPARATION:The reaction between a halomethylnaphthalene of formula II (Y is halogen) and m-hydroxybenzamide derivative of formula III or between a m-naphthylmethoxybenzoic acid or its reactive derivative and an amine of formula V give the compound of formulaI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific adozoic acid derivative and a herbicide containing the same.

The present inventors focused on compounds with a benzoic acid group and investigated their herbicidal activity, and discovered the specific retarding action of a specific benzoic acid group and completed the present invention. Cane.

The first invention of the present invention is based on the general formula [wherein the above and below are a hydrogen atom, a lower alkyl group,
Lower alkenyl group, lower alkyl group! represents a lower alkoxy group, a lower flukoxyfurkyl group, or a lower ^rofurkyl group. In addition, with the nitrogen IAM element in the formula H and H#i, a saturated** ring may be formed with 4 and 5 carbon atoms (one carbon may be replaced with an oxygen atom). . ] The second invention is a herbicide containing the benzoic acid compound.

Next, typical benzoic acid fumid derivatives according to the present invention are shown.

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

[However, in the formula, Y represents a halogen atom.
In the formula, the compound is reacted with a meta-hydroxybenzoate compound represented by the following formula.

That is, 1-^romethylnaphthalenes [Place] and metahydroxybenzoic acid amide derivatives [Place] are heated in the absence of a solvent or in an inert organic solvent in the presence of a dehydrogenating agent to cause a reaction. Inert solvents include toluene,
Suitable solvents include dichloromethane, dimethylform fluoride, dimethyl oxide, sedum, and mixtures thereof.

As a dehalogenating water bulking agent, it is preferable to use sodium carbonate, carbonate, etc. The degree of reaction source and reaction time vary depending on the type of reagent used, but in general, 50C & Ishisen Meteor Degree, 11 to 1
After completion of the reaction, which is preferably 0 hours, the desired metal product can be converted into a reaction mixture according to a conventional method.

(1) Metanaphthylmethoxybenzoic acid represented by the general formula or a reactive derivative thereof and the general formula [wherein x and iirtw are defined as above]. ] is reacted with RYOZノ.

9. Reactive derivatives include acid halides, acid anhydrides, esters, and the like.

This reaction is carried out without a solvent or in an inert organic solvent. Among the free acids and reactive derivatives, acid talolides are commonly used and the reaction is carried out in the presence of a dehydrochlorination agent. The acid chloride used is synthesized from the free acid and thionyl chloride or phosgene.

Suitable inert organic solvents include toluene, xylene, diethyl ether, tetrahydrofutun, dioquinano, dichloromethane, carbon tetrachloride, ethyl acetate, and mixtures thereof. Further, it is appropriate to use #i1 as a dehydrochlorination agent, such as triethyl ane, sodium hydroxide, sodium carbonate, etc. Since the reaction is a general #C exothermic reaction, it is usually carried out under cooling.The reaction time varies depending on the main WcIL reaction temperature and the compound used, but it ranges from an instant to several hours. After the reaction is completed, the target compound can be obtained from the reaction mixture according to a conventional method.

Next, a typical synthesis example will be shown.

Synthesis Example 1 N,N-dimethyl 5-(1-t7thylmethoxy)benzoic acid amide N,N-dimethyl 3-hydroxybenzoic acid amide 1a
, 1F, 17.4F of 1-trimethylnaphthalene, and 166 tons of potassium carbonate were dissolved in 15 ml of dimethylformamide and stirred at 100° C. for 1 hour. After the IL reaction was completed, the reaction mixture was poured into 5005 g of 0 tubes, and the precipitated crystals were fully dried to obtain 29.9 g of crude crystals. I got st. This was recrystallized from benzene/n-hexane from Oa Taiwan, N,N
-Dimethyl 5-(1-su7tylmethoxy)benzoic acid amide 215t was obtained. Melting point 61~! ? 1C, yield 7CLi
It was X (tar methyl base).

Elemental analysis value (c, pigeon, NO:) Calculated value: C71
L+69 H&25 N415? Experimental value: C71L
57 H451NL6SI B (Nujo Hoho, t
i large-accps-') 1m$30 1440
1297 124s Synthesis N2 N-Ethyl 3-(1-7thylmethoxy)benzoic acid amide 3-(1-7thylmethoxy)benzoic acid tallolide 50 tons of tetrahydrofuran port solution was stirred under cooling in a water bath. While stirring, 70% ethyl ryoden amino solution 3- was added dropwise, and after the dropwise addition was completed, the reaction solution was stirred for 30 minutes at room temperature.
The precipitated crystals were separated and dried to obtain 2.9 tons of crude crystals. Add this to toluene lida ■
Recrystallization from an oxidation solvent gave 2.2 tons of N-ethyl 3-(1-7thylmethoxy)benzoic acid amide. Melting point: 108-110°C Yield: 72. IX (*Lupon Shun chloride basis).

Elemental analysis value (as C2, pigeon, NO3) Calculated value: Cya
at H42! I N4. lS? Experimental value ZCIFL
IS H457N4411 R (NuJO1 method, S large absorption 5+-1) 3210 1420 1540
1240 The herbicide of the present invention is prepared by mixing a compound represented by the general formula [1) with various carriers as an active ingredient,
It can be obtained by preparing Form 11KII formulations such as wettable powders, emulsions, powders and granules. Among the carriers, liquid carriers include:
A commonly used organic solvent is used, and a commonly used mineral fine powder is used as the integral carrier. Also made by formulation j! During iK, a surfactant is added to impart emulsifying properties, dispersibility, spreading properties, and the like. In addition, other agricultural chemicals such as fertilizers, herbicides, insecticides, and cocoonicides may be used in combination.

When used as a herbicide, the active ingredient compound is sufficiently concentrated to exert the desired herbicidal action.

Its mM amount is active ingredient 11%AL1000f/10ae
It is applied within the range, but Tatami Haruka is 11 to 10009/l.
ea, and to get 1 is 100tk or 500F/1
0m #! < For use in other forms such as wettable powders, emulsions, powders, granules, etc. containing the active ingredient (L1*hLSO*%fh
Wow.

To make an emulsion, the active ingredient is dissolved in an agriculturally acceptable organic solvent, and a #III & soluble emulsifier is added.

Suitable TK solvents are Harutomizu and mild Shikuraai 10.

Hydrocarbons, chlorinated hydrocarbons, ketones, esters, chloroethylene, cycloethylene and dimethylformamide or mixtures thereof can be added. Particularly suitable #11 solvents are aromatic hydrocarbons and ketones, but Haruka uses solvent t>a compounds.

The surfactant used as an emulsifier occupies about 15' to 20 parts by weight of the emulsion, and has a range of 4, 4, 4, 5, 4, 4, 4, 4, 4, 4, 5, 6, 6, 6, 7, 9, 10 to 10,000 surfactants are used as emulsifiers.
Alternatively, it may be nonionic.

Anionic surfactants include alcohol 7A) t*
H sulfo$-), alkylaryl sulfonates or sulfosuccinates, such as calcium dodecylbenzenesulfonate or t)lium dioctylsulfosuccinate.

Cationic surfactants include aliphatic acid salts and fatty acid alcohol quaternary salts, such as lauryl acid hydrochloride or dimethylbenzyl ammonium chloride.

Non-ionic emulsions that can be used include mKa, phenol in alcohol, fatty alcohols, mercaptans and ethylene oxide adducts of fatty acids, such as polyethylene glycol esters of stearic acid or polyethylene glycol esters of electrolytic alcohol or octylphenol. v:
Mention may be made of 1-lether.

The concentration of the active ingredient is 80 parts by weight, especially Kl 0.
A suitable range is 1 to 50 parts by weight.

Wettable powders are prepared by adding the active ingredient to an inert finely divided solid carrier and a surfactant. Traditionally, the active ingredient is present in the range of 5 to 50 parts by weight, and the surfactant is present in the range of 15 to 20 parts by weight.

Solid carriers commonly used for formulating the active ingredients are naturally occurring clays, silicates and silicas, limes and carbonates and 1R organic carriers. Typical examples of these are kaolin, gicrite, aller's earth, tarta, siliceous earth, magnesium lime, dolumite and walnut flour.

Commonly used emulsifiers and thickeners are PoliodPV ethylenized alkylphenols, fatty alcohols, fatty I! and alkaline compounds, alkylaryl sulfonates and dialkyl sulfonaccinates.

Glycerin is a spreading agent! Examples include materials such as nitrate and phthalic anhydride-modified conjugates of oleic acid and phthalic anhydride.

Dispersants include maleic anhydride and olefins such as diinoptylene copolymers. For example, sodium lignin sulfonate, sodium lignin sulfonate, and formaldehyde sodium sulfonate are used.

Powders contain the active ingredient in an inert carrier commonly used in the manufacture of powders, such as talc, pulverized clay, quartz clay,
Madanesium carbonate or = produced by blending with wheat flour.

Concentrated powders containing active ingredients in the range of 1 and 80 parts by weight have been around for a long time, but they can be applied as herbicides.
The AK is diluted to about 11 to 20 parts by weight with additional solids.

Granules contain active ingredients in agricultural carriers such as bentonite, kaolin talley, and kaolin tal IK.
Since the amount of active ingredients for m people is K, these granules contain 11 active ingredients! Contains 50 parts by weight of Nishi.

The herbicide of the present invention exhibits herbicidal activity against grasses known as highly harmful weeds such as Japanese grasshopper, Japanese cypress, and Japanese chickweed. Moreover, no chemical damage to rice was observed at all.

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

Specific examples for the preparation of the agent of the present invention are shown below.

ik or "parts" means "parts by weight".

Example 1 (emulsion) Compound number - 225 parts Medium sire ν 35 parts Cyclohexanone gos Crane pole 800mm 10 parts (Toho Chemical Trademark) The emulsion of the present invention was obtained by homogeneously dissolving the mixture with KA.

Example 2 (hydration N) Compound scent @-1750 parts Kaolin clay 4511 Norbor 5059 Part 5 were mixed and ground to obtain a wettable powder of the present invention.

Example! + (powder) Compound number-tS　　　　S part Kaolin clay 95 parts The mixture was mixed and ground to obtain the powder of the present invention.

Example 4 (Grain M) Compound No. - 215 parts Bentonite 45 parts Talc 45 parts Lignosulfonic acid 5 parts were homogeneously ground with eca, mixed with water and kneaded), granulated and dried to obtain the granules of the present invention. Obtained.

Next, the usefulness of the metal compound according to the present invention will be demonstrated in the following test examples. I will clarify.

Test example (Paddy soil treatment N) After filling a teaIO pot with a diameter of 115 am and a depth of teaIO with paddy soil and adding paddy soil containing 61i paddy weeds to the surface layer,
Fertilization was applied for one generation, and the soil was filled with water to 3. Two paddy rice plants (product H: Nihonpare, 1+2.5m1 JI11) were transplanted. Four days after transplanting paddy rice, a predetermined amount of the diluted solution obtained by cutting ice according to the present invention was dripped into the water.

The investigation was conducted on the weeding effect and paddy rice K on the 2nd day after 111M.
We observed the presence or absence of hive nests. The results are shown in Table 2, and the evaluation in the table is based on the following one.

Herbicidal effect index Phytotoxicity index 5: Complete herbicidal effect -: Harmless 4: Herbicidal effect of 80-90% Certification: Small book 5: Weeding effect of 66-798
+: Small book 2:40-5? Weeding effect of X Mother: Human damage 1
: 20-! ! 9% Weeding effect I: 0
! Weeding effect below 20X X: Dead side
Continuation of the table on page 1 (Inventor: Yasuya Sakuraba, Hodogaya Chemical Co., Ltd. Central Research Laboratory, 6-2-30 Oji, Kita-ku, Tokyo; Inventor: Takayuki Isoyo, Tora, Minato-ku, Tokyo) Mon-chome 4-2 Hodogaya Chemical Industry Co., Ltd.

Claims (1)

[Claims] General formula [wherein R1 and island in formula 1 are hydrogen atoms, lower alkyl groups, lower alkenyl groups, lower terkynyl groups, lower thyl;
Represents xy group, lower thyl; xyalkyl crystal, lower haloalkyl group. - and 4 are the nitrogen atoms and - in the formula, and the number of carbon atoms of 4 and 5 (and one carbon is #I
may be replaced by an I-chord atom) to form a saturated heterocycle. ] benzoic acid ado derivative. 2 general formula [However, R in the formula, and 8. represents a bulky atom of water, a lower alkyl group, a lower fulkenyl group, a lower terkiel group, a lower thyl-oxy group, a lower 7k: 2* sial group, a lower xw alkyl group; With atoms, the number of carbon atoms of 4Th and 5 (moreover, the carbon 1
A herbicide containing a benzoic acid te-electrode attractant represented by ], in which %A) may be replaced with an oxygen atom to form a saturated complex.