JPS5841869A - Isonicotinic acid anilide, its preparation, and plant growth regulator comprising it - Google Patents

Abstract

NEW MATERIAL:An isonicotinic acid anilide derivative shown by the formulaI[R1 is lower alkyl; R2 is H or lower alkyl; A is -C(=O)- or -C(OH)H-; X is halogen with the proviso that isonicotinic acid-4-acetylanilide is omitted]. EXAMPLE:Isonicotinic acid-2-acetylanilide. USE:A plant growth regulator. Having improved effect especially on gramineous plants. PROCESS:For example, an isonicotinic acid halide derivative shown by the formula II (Y is halogen) is reacted with an aniline derivative shown by the formula III, to give an isonicotinic acid anilide derivative shown by the formulaI.

Description

[Detailed description of the invention] General formula (I) covered by the present invention R.

(In the formula, R1t! represents a lower alkyl group, - is a hydrogen atom, except for inocotin-4-acetylanilide)
The innicotinic acid anilide derivative represented by the above formula, its production method, and its composition are useful for plant growth regulators comprising two or more types of compounds. Although the compounds of the present invention are effective against all kinds of plants, they exhibit particularly excellent effects against grasses.

One of the major changes in Kinto's 11 crops is the progress in mechanization of planting and harvesting. Therefore,
Recent rice cultivation technology Km-1 is used for mechanized transplantation and light value is 1
% of owned technology that can prevent lodging at the same time as education and interpretation
has become an important issue. In other words, Koshihikari and Sasaniji dP Go, which are said to be branded rice, have extremely high reputations for taste, but on the other hand, they are extremely susceptible to lodging, and they also have the disadvantage of being susceptible to many diseases. Therefore, it is desired to establish a microscopic examination technique that can raise healthy rice seedlings and also be expected to be K11i%/& mechanically adaptable at the time of harvesting, or to develop a growth control method Ov/A using drugs.

The present inventors have conducted repeated studies for several years on compounds that have a growth-regulating effect on various plants, mainly rice, and have found that the innicotinic acid anilide conductor represented by the general formula (I) is a compound that has a growth regulating effect on various plants, mainly rice. He discovered that plants exhibit a revolutionary growth regulating effect and completed the invention.

The compound represented by the general formula (1) can be widely used in rice, for example, to prevent elongation in seedling boxes and seedling beds, to prevent aging, and to prevent lateralization in transplanted paddy fields, and can also be used to increase yield. It is possible to produce WK wheat.

The same effect as on rice can be achieved on cornflowers, sugar beetles, etc. It is also effective in preventing the elongation of the hypocotyls of Japanese cabbage, eggplant, and cylindrical seedlings.

On the other hand, applying it to lawns is also one of the most effective ways to use it. In recent years, lawns have been used in ordinary homes, golf courses.

Green belts, road shoulders, green belts, etc. - Although often used and obstructed,
Not only is its management very picturesque, but it also requires a great deal of effort to reap when it grows actively in the summer.
Furthermore, huge expenses are required.

Many gramineous plants are used for turf grass on the E1 area, on general roads, expressway shoulders, greenbelts, expressways and railway slopes, and their management requires a great deal of labor and economic risk. It is not a big deal, and the maintenance work involves great danger, so the application of Honkei's compound to such situations is of great significance.

In addition, the compound represented by the general formula (1) can be used for both grasses and broad-leaved plants, as mentioned above, and is expected to increase resistance to poor environments and pests. I can do it.

It has a wide range of effects, including promoting photosynthesis by increasing the number of spellings, promoting carbohydrate production, and promoting lateral growth.

The major characteristics of the compound of the present invention are that it strongly inhibits plant growth, 4IK plant height growth, darkens the leaf color, and It is possible to grow healthy plants without causing any chemical damage such as dead leaves or dead plants.

The compound of the present invention represented by the general formula (Otori) is novel,
It can be manufactured by the method shown below.

(1) Isonicotinic acid halide represented by general formula (1) (wherein Y represents a halogen atom) is added to general formula (■) (wherein R1, R1A, and X are the same as above) in a suitable solvent. The compound represented by the general formula (1) is produced by reacting with the aniline derivative represented by ).

In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. In addition, suitable solvents include, for example, benzene,
Toluene, xylene, dichloromethane, chlorotetraform,
Examples include tetrahydrofuran, dioxane, dimethylformazde, and the like. Examples of deoxidizers include pyridine,
Examples include triethyl acetate, sodium hydroxide, potassium chloride, sodium carbonate, and potassium chloride.The reaction temperature f can proceed even at room temperature, but depending on the case, it may be carried out by cooling or heating, preferably from 0 to One reaction time, preferably 60°C, depends on the selection of conditions, but after the completion of the 0 reaction, which can be completed in 1 to 8 hours,
The desired product can be obtained by separation and purification using conventional methods.

(Rumor general formula (W) 2゜(In the formula, R1*R1 and X have the same meanings as above, ・・・・・・・・・・・・・・・・・・・・・・・・・・・
The compound represented by formula (1) can be easily produced by reducing the isonicotinic acid derivative represented by K with an appropriate reducing agent. 4!17i: Examples of the agent include lithium aluminum hydride and sodium borohydride. can.

Production Example 1゜Isonicotinic acid-2-acetylanilide (compound number 3
) Preparation method 2-Aranoacetophenone 135F is added to pyridine 30dK
After cooling the solution with ice and stirring, 114f of isonicotinic acid tetralide hydrochloride was added little by little.Then, the mixture was stirred at room temperature for 8 hours, and after death, 100 dl of water was added to the reaction solution.
When added, crystals precipitate and form a tiger.

When this crystal was subjected to PIE and recrystallized from duck-hexane-acetic acid ethyl ester mixed medium #I, isonicotinic acid-2-
Add 2.23t of acetylanilide (yield 9396) lI, m point t 16~l l 7℃ element 5+ analysis flll=O
saHs*N*Oz molecule t24a26o
HN Calculation 1ii1tj@69.99 5.03 Within 1166 actual measurements 7α08 498 1L6G Production Example 2 Isonicotine 1! Production of -2-acetyl-4-tarroa-lide (compound number 6) In the same manner as in Production Example 1, using 17t of 2-aonoacetophenone in place of 2-aonoacetophenone in Production Example 1. The reaction was carried out to obtain 1SP of isonicotine*-2-acetyl-4-chlorogastric anilide (yield 9ON), melting point 203-205'C7C element'ffr fil:
0s4H1tOANxO* 5+ molecular weight 274710
HN Calculated value 1fi4 6L21 to< 1a2e
Actual value -61093,991&24 Production example 1 Production of isonicotinic acid-4-chloro-2-<6-hydroxyethyl)anilide (compound number 7) 9 Isonicotinic acid-2-acetyl-4 obtained in Production example 2
- Chloraeli 8doz5f methanol 3olljK+
l! Dissolved, cooled with water, and stirred with 0.0% sodium borohydride.
Add 34f little by little. After stirring at room temperature for 3 hours,
Methanol was removed under reduced pressure, and 100 μm of water was added. Crystals were precipitated into circles. When the crystals were defeated and recrystallized from a mixed solvent of duck-hexane-ethyl ester, isonicotine #-4-chloro-2 was obtained. 232 (yield: 929 g) of -(-monohydroxyethyl)anilide was obtained. Melting point 142-1.
．． 43℃ elemental analysis value: 014H1301N101
Molecular weight 276.620 HN Calculated value (2) 6α77 474 1a12 interference value (
) 6α70 Table 77 1αO8 Next, the general formula [! ] Typical examples of compounds represented by # are shown in Table 1.
The compound numbers are also referred to in the following Examples and Experimental Examples.

In the plant growth regulator of the present invention, it is appropriate to use one or a mixture of two or more of the compounds represented by the general formula (1) at a ratio of usually 5G to 1000f per 10 ares. Needless to say, the dosage can be adjusted as appropriate depending on the purpose of use and the situation of the plant.

9. When formulating, it can be mixed with various solid and liquid carriers used in the preparation of general bird medicines to produce aquariums, emulsions, powder tablets, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, penetrants, and binders may be added to the drug.Depending on the purpose of use, the above components may be combined with other herbicides, monocides, It can be used in combination with insecticides, plant growth regulators, fertilizers, etc.

Next, the effects of the present invention will be explained in detail with reference to experimental examples.

Actual example L Early growth control test of cucumber and rice (diameter 9ex)
'Place a sheet of JInlKF paper, add 15 d of aqueous solution of the test compound at a predetermined concentration, and add 1 Nakajima chestnut (Kiwa) seeds to it.
0 seeds and 10 seeds of rice (variety: Nasanishi) were placed on the bed respectively, and the test was carried out with 1 (!) amount of 3 repetitions for each seed.
Managed and raised within Lutx's Phytotron. Seven days after the chemical treatment, in the case of cucumber, the hypocotyl length, width, dry weight of the shoot and leaf part, and dry weight of the root part were measured, and in the case of rice, the plant height, length of the 2nd j111, width, and dry weight of the shoot part were measured. The weight and root dry weight were measured, and the results are shown in Table 2 for Fi-medium gourd and Table 3 for rice.

The numerical values shown in Tables 2 and 3 are average values of 30 individuals.

Back - Example 1 Experimental example I of rice growth prevention test using rice seedling bed soil mixture treatment IIIK
Hydrating agent 2f of each test compound prepared according to the formulation according to K.
, 1f and a5t are uniformly mixed in 4# soil, and 12# is placed in a plastic perforated rice seedling box (vertical 30 ts Koshihikari) 150 ft- sown,
After wetting, the soil was covered with 6 as#o soil. The exam is 25-3
The seeds were allowed to germinate for 2 days in a 97-item (97-item) chamber with the temperature adjusted to 0C, and then grown outdoors in a vinyl 7-frame chamber. The investigation was conducted by measuring plant height, root length, leaf age, stem weight, and S weight on the 20th day of sowing, and the results are shown in Table 4.

The numerical values shown in Table 1 are the average values of 50 individuals.Next, examples of the present invention will be shown, but the compounds, carriers, and formulations used are the same as in this vI! It is not limited to examples.

Example Compound No. 2 56 parts by weight Sodium sulfate in alkali 15 #Polyoxyethylene alkyl phenyl ether 15.

, Rishi −
45 # Make these uniform! Mix well and pulverize to obtain an irrigation agent.

Example 1 Compound No. 7 10 Parts by weight Lidanine sulfone natrichum l #Bentonite
30 l talc s9I Mix these thoroughly until uniform and granulate to obtain granules.

Example 1 Compound No. 12 10 parts by weight Polyoxyethylene ruphenyl ether in alcohol 7I Calcium alkylaryl sulfonate 3 #xylene
601 Cyclohexanone 20 I These are thoroughly mixed and dissolved until uniform to obtain an emulsion.

Applicant: Chugai Pharmaceutical Co., Ltd. Continuation of page 1 0 shots clear person Masahiro Yoshimoto 3-41-8 Takada, Toshima-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd. 0 shots by Yoshitaka Iwane.

3-41-8 Takada, Toshima-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd. 0 shots by Yasushi Murakami 3-41-8 Takada, Toyosai-ku, Tokyo Inside Chugai Pharmaceutical Co., Ltd.

Claims (1)

[Claims] l) The general formula represents a -δH- group, and X represents a halogen atom. However, excluding innicotinic acid-4-acetylanilide
) An inonicotinic acid anilide derivative represented by 2) General formula %Formula % (In the formula, ! represents a hydrogen atom) is an innicotine-exclusive conductor and the general formula (In the formula, R1 represents a lower alkyl group, Bl represents water, A general formula characterized by reacting Che9/derivatives represented by the following formula (in the formula, ax e R1am and 3) General formula (in the formula, ml represents a lower alkyl group, R4 represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom) showing,
・・・・・・・・・・・・O・・・・O・・・・・・・
) An isonicotine anilide conductor OS manufacturing method represented by the general formula (wherein -0B3 and X have the same meanings as above), characterized by reducing an inonicotinic acid U conductor represented by: 4) General formula However, isonicotinic acid-4-acetylanilide is
) 01 types of ino-cotinic acid anilide derivatives ★
1. A plant growth regulator characterized by containing two or more types of edible seeds as active ingredients.