JPH0225466A - Alpha-substituted ketone derivative and herbicide containing the same derivative - 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 [Industrial Application Field] The present invention relates to -form (I) F' (wherein X is a hydrogen atom or a chlorine atom, and R1 and R2 are each independently a hydrogen atom or a lower alkyl group) , R3 is an alkyl group, alkenyl group, aryl group or aralkyl group, or R2 and R3 together represent an alkylene group having 3 or 4 carbon atoms)
- Substituted ketone derivatives or salts thereof, and herbicides containing them as active ingredients.

The lower alkyl groups represented by R1 and R2 in general formula (1) are typically methyl, ethyl,
1 or more carbon atoms such as n-propyl group and isopropyl group
Examples of the alkyl group of group R3 include lower alkyl groups having 1 to 5 carbon atoms such as methyl group, ethyl group, n-propyl group, and isopropyl group, and examples of the alkenyl group include: Examples include alkenyl groups having 2 to 6 carbon atoms such as vinyl groups and allyl groups; examples of aryl groups include aryl groups having 6 to 12 carbon atoms such as phenyl groups, p-chlorophenyl groups, and tolyl groups, and substituted Examples of the W substituent include halogen, an alkyl group having 1 to 3 carbon atoms, and an alkoxy group having 1 to 3 carbon atoms; examples of the aralkyl group include a Hensyl group,
Examples include aralkyl groups having 7 to 15 carbon atoms such as p-chlorohensyl group, and substituents thereof (for example, \rogen, alkyl groups having 1 to 3 carbon atoms, and alkoxy groups having 1 to 3 carbon atoms). .

[Conventional technology]

A series of pyridyloxyphenoxy compounds such as 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid have been developed as important herbicides in agriculture and horticulture. Unexamined Japanese Patent Publication 1973
-22371 and Japanese Patent Application Laid-open No. 54-24879). These pyridyloxyphenoxy herbicides are safer than the previous phenoxy herbicides, have less impact on useful cultivated plants, and have a strong herbicidal effect. However, these pyridyloxyphenoxy herbicides have low selectivity for monocots, cause damage to useful plants such as rice, wheat, and barley, and are not effective against some perennial weeds. Therefore, its application situations and usage were extremely limited.

[Problem to be solved by the invention]

Therefore, the present invention maintains the properties of these p-phenoxyphenoxypropionic acid-based herbicides and p-pyridyloxyphenoxypropionic acid-based herbicides, and has high selectivity among grasses, such as rice and wheat. Another object of the present invention is to provide a novel α-substituted ketone derivative, which is a herbicide that does not cause harmful effects on barley, etc., and a herbicide containing the same as an active ingredient.

[Failure to solve the problem]

According to the present invention, there are provided α-substituted ketone derivatives represented by the above-mentioned formula (I) and salts thereof, which are compounds having a strong herbicidal effect, and herbicides containing the same as active ingredients.

[Specific explanation]

The α-substituted ketone derivative shown in form (1) of the present invention can be produced, for example, by the following method.

That is, an amine salt of the form (1'l) (wherein X and T are as defined above) and the general formula (I[r) X'-C-COR' (III)
(In the formula, Xl represents a chlorine atom or a bromine atom, and R1
, R2 and R3 are as defined above).

Examples of the amine in the above production method include general dialkylamines, trialkylamines, etc., and a preferred example is dicyclohexylamine.

Further, the reaction is carried out in an aprotic polar solvent, and such a solvent is not particularly limited, but suitable examples include dimethylformamide and dimethyl sulfoxide. The reaction temperature is usually θ°C to 100°C, preferably room temperature to 60°C.

Moreover, the reaction is generally completed in 0.1 to 3 hours.

After completion of the reaction, the compound of the present invention obtained as described above can be purified using general purification methods such as recrystallization, column chromatography, thin layer chromatography, etc., if necessary.

Note that the compound according to the present invention has optical isomers based on two asymmetric carbon atoms, and all of these are included in the present invention.

The compounds of the present invention thus obtained have low toxicity to humans and livestock, and have extremely specific and strong growth-inhibiting activity against monocots. This suggests that the compounds of the present invention can be widely used as agricultural chemicals.

When applying the compound of the present invention as a herbicide,
Generally, it can be applied in combination with a suitable carrier, such as a solid carrier such as clay or diatom, or a liquid carrier such as water, alcohols, aromatic hydrocarbons, ethers, ketones, or esters. If desired, emulsifiers, dispersants, suspending agents, spreading agents, stabilizers, etc. can be added to provide formulations such as emulsions, wettable powders, granules, and powders. It may be applied in combination with herbicides, various insecticides, fungicides, plant growth regulators, etc.

In practicing the invention, the concentration of the compounds of the invention can be varied over a wide range;
．． It is preferable to use it in a range of 5 to 10 g. When manufacturing the various formulations mentioned above, they can be manufactured so as to contain the active ingredient in a range of 0.5 to 90% by weight.

〔Example〕

The present invention will be explained in more detail below using production examples, test examples, and formulation examples, but it goes without saying that the technical scope of the present invention is not limited to these examples.

Production flaming 2- (4-(3-chloro-5-trifluoromethyl-
2-pyridyloxy)phenoxy)propionic acid 2-
Oxopropyl ester (compound number 1) 2-(4-(3-chloro-5-trifluoromethyl-2
-pyridyloxy)phenoxy)propionic acid 3.62
g Dissolved in 50 mβ of dimethylformamide, added 2.2 mfl of dicyclohexylamine, and stirred at 60°C. Add 1.02g of chloroacetone to this and add 60g of chloroacetone.
The mixture was stirred at °C for 3 hours. 100 ml of water to the reaction mixture;
was added, extracted with toluene, washed with water, and dried over anhydrous magnesium sulfate. The oil obtained by distilling off the solvent under reduced pressure is
The mixture was subjected to medium pressure column chromatography on silica gel (n-hexane:ethyl acetate-9: 1 v/v%) to obtain the title compound 4, OOg, as a colorless oil. (Yield 96%) Compound No. 2 was also produced by the same method as in Production Example 1 above.
~11 was synthesized.

The structures and physical properties of all the compounds synthesized above are shown in Table 1.

1(,-) 1- I X 7. Field soil was filled in l cm square pots, and after sowing golden millet, crabgrass, giant knotweed, and blueberry, the soil was covered with 51 kg of soil, and a predetermined dose of the test compound was diluted with water. After treatment, the plants were kept in a greenhouse for 20 days, and the herbicidal effect was observed and evaluated according to the following criteria, and the results shown in Table 2 were obtained.

5: Completely dead 4: Daikichi 3: Used 2: Small book 1: Slight scent 0: harmless Bud-”shi-ten.

7. Fill a square pot of I x 7.1 cm with field soil, sow golden millet, crabgrass, Japanese knotweed, and blueberry. After covering with 5 ml of soil, grow in a greenhouse for 7 days to form two-leaf stage plants. A predetermined dose of the test compound was diluted with water, and IOLs per are were subjected to foliar treatment. After processing, 2
The herbicidal effect was observed and evaluated using the same criteria as in Test Example 1, and the results shown in Table 3 were obtained.

The plants were kept in a greenhouse for 20 days, and the herbicidal effect was observed and evaluated using the same criteria as in Test Example 1, and the results shown in Table 4 were obtained.

7. ] Paddy soil was filled in a square pot measuring 7.1 cm x 7.1 cm, and the pot was flooded to make it into a paddy field. After sowing Japanese millet and Japanese grasshopper, a predetermined dose of the test compound was diluted with water, and the pot was poured onto the water surface with a pipette. Dropwise treated. After processing, 7, I
7. Fill a square-shaped bot of 1 ctn with paddy soil, flood it to make it into a paddy field, and after sowing Japanese millet and Japanese paddy,
The plants were grown at room temperature for 7 days to obtain two-leaf stage plants, and a predetermined dose of the test compound was diluted with water and dropped onto the water surface of the pot using a pipette. After treatment, the plants were kept in a greenhouse for 20 days, and the herbicidal effect was observed and evaluated using the same criteria as in Test Example 1, and the results shown in Table 5 were obtained.

15 parts by weight of this compound (compound number 1) as an active ingredient, 65 parts by weight of xylene and 20 parts by weight of polyoxyethylene alkyl allyl ether are mixed to make a homogeneous solution,
An emulsion containing 15% of the active ingredient compound was obtained. When using, dilute with water to the specified concentration and spray.

Production side ■1] Mix and grind 40 parts by weight of this compound (compound number 3) as active ingredients, 55 parts by weight of gicrite, 2 parts by weight of sodium alkylbenzenesulfonate, and 3 mmts of polyoxyethylene alkylaryl ether. A wettable powder containing 40% of the active ingredient compound was obtained.

When using, dilute with water to the specified concentration and spray.

5 parts by weight of this compound (compound number 6) as an active ingredient,
20 parts by weight of bentonite, 73 parts by weight of clay and 2 parts by weight of sodium dodecylbenzenesulfonate were mixed, and about 2 parts by weight of water was added.
After adding 0 parts by weight and kneading with a kneader, the mixture was granulated through a granulator, and then dried and sized to obtain granules containing 5% of the active ingredient.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X is a hydrogen atom or a chlorine atom, R^1 and R^
2 is each independently a hydrogen atom or a lower alkyl group, R
^3 represents an alkyl group, alkenyl group, aryl group, or aralkyl group, or R^2 and R^3 together represent an alkylene group having 3 or 4 carbon atoms) Or its salt. 2. A herbicide containing the compound according to claim 1 as an active ingredient.