JPS6016950B2 - New naphthoxy compounds - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a naphthoxy compound represented by the general formula (wherein R, R2 are hydrogen atoms or methyl groups) and herbicides containing the compound as an active ingredient.

The compounds of the present invention have the ability to control weeds without causing chemical damage to field crops and paddy rice.

That is, the compound of the present invention represented by the general formula m exhibits a remarkable killing effect on weeds such as morning glory, chinese fir tree, chickweed, whiteweed, and silverweed, which are problematic in field crops, but is harmless and selectively kills crops such as corn and wheat. Grass is recognized, and for wet rice cultivation, annual and perennial broad-leaved weeds such as azalea, Japanese azalea, Japanese azalea, Japanese knotweed, Japanese violet, Japanese cypress, Japanese chickweed,
It exhibits a remarkable blighting effect on Japanese cypress, Japanese cypress, Japanese cypress, and weeds of the Cyperaceae family, namely, Japanese cyperus, Japanese firefly, Japanese cypress, Japanese cypress, Japanese cypress, and Japanese cypress, but no phytotoxic effects such as deformed leaves or other harmful effects are observed on paddy rice. For the control of broad-leaved weeds in paddy fields,
The phenoxy herbicides 2,4-D and NCPA have been widely used, but depending on the time of use, soil or weather conditions, they can often cause paddy rice damage, so it is important to use an accurate herbicide. The development of this is strongly desired.

The compound of the present invention is an extremely safe herbicide that can accurately control broad-leaved weeds and cyperus weeds without causing any harm to paddy rice under any of the conditions described above.

Next, the compounds of the present invention represented by the general formula {1) are illustrated in Table 1 below, and the manufacturing method thereof will be explained with reference to Examples.

Table 1 Example 1 Synthesis of 2-[1-(3-naphthoxy)ethyl]-A2-oxazoline (compound m) Methanol 30% N-(
P-chloroethyl)-Q-(8-naphthoxy)propionamide 2.8 moles (0.01 mol) [which can be synthesized from Q-(8-naphthoxy)propionic acid and 3-chloroethylamine by a conventional method] is melted. To this was added aqueous sodium hydroxide solution 3' at room temperature.

Thereafter, the reaction was carried out by stirring at 45 to 50 qo for 5 hours. After the reaction is completed, the reaction solution is discharged into 200ml of cold water,
The mixture was saturated with potassium carbonate, extracted with shaking over benzene 200, and the benzene layer was washed with water, dehydrated, and the benzene was distilled off under reduced pressure. This residue was recrystallized with n-hexane to produce a pure product of the desired product (m.p.: 93-94.
5°C, yield: 62%). In addition, compound (1), (
B) and (W) can also be synthesized by this method.

Example 2 Synthesis of 2-[1-(8-naphthoxy)ethyl]-4,4-dimethyl-△2-oxazoline (compound W) 2-(Q
-Chlorethyl〉-4,4-dimethyl-△2-oxazoline 6.4 moles (0.04 mol), 8-naphthol 4.
3 moles (0.03 mol) and potassium hydroxide 2.3 moles (0
．． 04 mol) was stirred under reflux for 3 hours in a mixture consisting of 30 M benzene and 3 mol of water.

After cooling, the reaction solution was drained into 50 cm of a 10% aqueous sodium hydroxide solution, 200 m of benzene was added, and extraction with shaking was performed. The benzene layer was thoroughly washed with water, dehydrated, and benzene was distilled off under reduced pressure. The residue obtained at that time was recrystallized with n-hexane to obtain a pure product (m.p.) of the target product (N).
:74-75qo, yield: 50%. Note that compounds (1), (0) and (m) can also be synthesized by this method.

Example 3 2-[1-(Q-naphthoxy)ethyl]-Δ2-oxazoline (compound 1) Q-(Q-naphthoxy)propionic acid 10.8 mol (0.05 mol) and 8-aminoethanol 3.1 Pour (0.05 mol) into a flask and gradually heat it to raise the internal temperature to 130-140°C. After the generation of water vapor has stopped, raise the internal temperature further to around 200°C for the second time. The reaction was completed by generating steam and stirring at the same temperature until the steam generation stopped.

After cooling the reaction solution, the contents of the flask were extracted with 200M benzene, washed with a 10% aqueous sodium hydroxide solution and then with water, dehydrated, and benzene was distilled off under reduced pressure. The residue was recrystallized from n-hexane to obtain a pure product of target compound (1) (m.p.: 54-55.500, yield: 6
1%). In addition, compounds (0), (m) and (W
) can also be synthesized using this method.

When the compound of the present invention is used as a herbicide, the dosage is 1 to 50 days per area, preferably 5 to 20 days, and can be applied by various methods such as soil mixed layer treatment, flooding treatment, and hollyhock treatment.

The compounds of the present invention can be applied directly or indirectly to the plants to be controlled.
It can be applied as a component in herbicidal compositions or formulations containing commonly used carriers.

In order to actually use the compound of the present invention, it is formulated into various dosage forms such as powders, granules, wettable powders, and emulsions. So 2-10
%, 40 to 80% for wettable powders, and 10 to 50% for emulsions. Examples of formulations of herbal medicines containing the compounds of the present invention shown in Table 1 as active ingredients are shown below.

In the examples, "parts" represent "parts by weight." Example 4 2 parts of emulsion compound 1, 7 parts of solvent naphtha, and 1 part of emulsifier Solpol 800 (trade name of emulsifier manufactured by Toho Chemical Co., Ltd.)
The emulsion was mixed and dissolved to obtain 10 anchor parts of the emulsion.

Example 5 Wettable powder compound D 4 anchors, bentonite 3 anchors, diatomite 2
The base material and 1 part of sodium ligninsulfonate are mixed and ground to obtain 10 parts of a wettable powder.

Example 6 7 parts of granule compound m, 6 parts of bentonite, 30 parts of talc,
After mixing 2 parts of sodium lauryl sulfate and 1 part of polyoxyethylene alkyl aryl ether, an appropriate amount of water is added and kneaded, and the mixture is granulated using an extrusion granulator in a conventional manner to obtain 100 g of granules. get the part.

Example 7 Powder Compound WI Etsuro, Keisouji 5 Kuni Ikari, and Clay 4
The side part is mixed and pulverized to obtain a base part of powder agent 10.

When the compound of the present invention is used as a herbicide, it is used in combination with one or more other herbicides, insecticides, agricultural chemicals such as plant growth regulators, soil conditioners, or fertilizing substances. Of course, mixed preparations with these are also possible, and synergistic effects can be expected in some cases. For example, examples of herbicides used in combination with the herbicide of the present invention include 2-chloro-2',6-diethyl-N-(butoxymethyl)acetanilide,
-Chloro-(2,6-dinitroanilino)-1N-methylpropionamide, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1-methoxy 1 -Methylurea, 1.1
-dimethyl-3-(3-trifluoromethylphenyl)
Urea, 2,4-bis(ethylamino)-6-methylthio-1,3,5-triazine, 5-chloro-4-methyl-2-propionamide-1,3-triazole, 2-
4,6-trichloro-4'-nitrodiphenyl ether, 2,4-dichloro-3'-methoxy 4'-nitrodiphenyl ether, S-(4-chlorobenzyl)-N.
These include, but are not limited to, N-diethylthiocarbamate, 4-chloro-2-methylphenoxyacetic acid, and the like.

Next, the herbicidal effects of the compounds of the present invention will be explained in more detail using test examples of herbicide activity. Test example 1 Paddy field initial weed killing test Paddy soil (through 9 squares) containing 3.3k9 of paddy field common weed seeds was placed in a 1/5000 Ahl Wagner pot, and N/P2Q, K20 each 0
．． After fertilizing the entire layer with chemical fertilizer on August 8th, an appropriate amount of water was added to make it flooded.

Hotaru seeds and Urikawa tubers were further added and sown, two rice seedlings (seedlings Aoi Rei 3.0) that had been raised in advance were used as one plant, and the two plants were transplanted and placed in a greenhouse. I let it grow. At the beginning of weed emergence 0 days after transplanting paddy rice, a predetermined amount of the test compound was submerged in water using a granule according to the method described in Example 6 above.

One month after the treatment, weed growth and chemical damage to paddy rice were investigated, and the results shown in Table 2 were obtained.

In this table, the display classification of weed outbreak status is according to the table below, and the display classification of the degree of chemical damage to paddy rice is "Ginzu", "Oisho", and "
There were six levels: medium harm, minor harm, harm caused, and harmless. During the test period, the depth of water in the pot was maintained at 3 skins by treating one skin per day.

Herbicidal activity Survival weed air dryer percentage 5
0%4 1~5% 3 6~30%2
31-55%1
56-80%0
81-100% evaluation of chemical damage Growth air dry weight percentage 0-9% major damage
10-29% Chinese
30-49% minor damage
50-79% slight harm 8
0-94% harmless 95-10
0% Table 2 * 2-Methyl-4-chlorophenoxyacetic acid sodium salt test example 2 Initial weed killing test in paddy fields Paddy soil in which seeds of common weeds in paddy fields are naturally mixed (through the grid on the 9th side) 3. Put 3k9 into a 1'5000 AR Wagner pot, add N・P205, K20 to it.
After fertilizing the entire layer with chemical fertilizer for 0.8 hours each, an appropriate amount of water was added to create a pseudo-flooded state.

Paddy rice seedlings that had been sown and raised in advance by adding firefly seeds and Urikawa soul stems to this
．． 0) Two plants were used as one plant, and the two plants were transplanted and grown indoors at a warm temperature. At the beginning of weed emergence 10 days after transplanting paddy rice, a predetermined amount of the test compound was submerged in water using a granule according to the method described in Example 6 above.

One month after the treatment, the appearance of weeds and the degree of chemical damage to paddy rice were investigated by observation, and the results shown in Table 3 were obtained.

In this table, the classification of the weed growth status was the same as in Test Example 1. During the test period, the depth of water in the pot was maintained at 3 skins by treating water leakage once a day.

Table 3 missing Sodium 2-methyl-4-chlorophenoxyacetate test example 3 Field crop foliage treatment weed killing test Field air-dried fine soil (through 9-row squares) 450 min.
/10,000 ares in a resin pot, add N,
Fertilize the entire layer of 100 females each of P205 and K20 with chemical fertilizer, and adjust the soil moisture to 60% of the maximum amount of water.

A certain amount of seeds of the joint test plants are sown in this, and after covering it evenly with soil, it is placed in a glass greenhouse. 2-3 co-trial plants
When the plants are grown at the establishment stage, 1 dose of each test drug with the active ingredient is added.
Stem straw treatment was performed using a hydrating powder prepared according to Example 5 so as to contain 0.000 to 2000 to 500 particles. After 30 days of treatment, the growth status of the test plants was observed and investigated.
The results shown in Table 4 were obtained.

In addition, in this table, the display categories of the growth states of crops and weeds are the same as in Test Example 1. Table 4

Claims (1)

[Claims] 1. A naphthoxy compound represented by the general formula ▲There are numerical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 and R_2 each represent a hydrogen atom or a methyl group.) 2 A disinfectant characterized by containing a naphthoxy compound represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 each represent a hydrogen atom or a methyl group) as an active ingredient. Herbal medicine.