JPH03169802A - Plant growth-regulating agent containing pyrimidine derivative as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a plant growth-regulating agent used for various purposes such as sprout promotion of seed or suppression of plant length readily applicable to plant by using a sort of pyrimidine derivative exhibiting ethylene-like activity. CONSTITUTION:The objective plant growth-regulating agent contains a pyridine derivative expressed by the formula [R1 is alkyl, (substituted phenyl or (substituted) phenoxy; R2 and R3 are H, alkyl, alkoxy or haloalkoxy, R1 is bonded with R2 to form (CH2)m or (CH=CH)2 ((m) is 3 or 4); R4 is H, alkyl, cycloalkyl, (substituted) phenyl or (substituted) benzyl; R5 is H, alkyl, alkoxy or halogen, R4 is bonded with R5 to form (CH2)n ((n) is 3 or 4); R6 is H, alkyl or alkoxy, etc.] or salt of said derivative (e.g. a compound of R1, R4 and R5 are CH3, R2 and R3 are H and R6 is O-C4H9-n) as active ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Application Field The present invention relates to a plant growth regulator containing a pyrimidine derivative as an active ingredient.

Conventional technology> Ethylene is a plant hormone that has been shown to have an effect on plants that promotes growth, flower bud formation, seed germination, abscission formation, fruit ripening, and healing tissue. It is said that UP B exhibits various effects such as promoting formation.
IOLOGY Plant Hormones pages 97-108 (written by Susumu Kuraishi,
University of Tokyo Press, 1976) and UP BIOL
It is known from OGY Ethylene, pages 82-114 (written by Noriyuki Shimokawa, published by the University of Tokyo Press in 1988).

Problems to be Solved by the Invention> However, since ethylene is gaseous, when treating plants with ethylene, it is necessary to isolate the target plants from other plants, and when treating at a predetermined concentration, There are many issues, such as the need to conduct the process in a closed system.

Means for Solving the Problems In view of this situation, the present inventors have conducted various studies and found that certain pyrimidine derivatives exhibit ethylene-like activity;
Furthermore, they discovered that it can be easily treated on plants, and completed the present invention. That is, the present invention provides R8 [wherein R1 represents an alkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxy group (here, the substituents of the phenyl group may be the same or different). It represents 1 to 8 "lower alkyl groups, lower haloalkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower alkenyloxy groups, lower alkynyloxy groups, or halogen atoms, and the substituents for the phenoxy group are the same or different 1 ~8 lower alkyl groups, lower haloalkyl groups, lower alkoxy groups, lower haloalkoxy groups,
Represents a lower alkenyloxy group, lower alkynyloxy group, cyano group, nitro group, phenyl group or halogen atom. ). R2 and R8 are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a lower haloalkoxy group. Also, Rl and R2 are bonded to -
(CHg)m- or -(CH-CH)2-(
Here, m represents an integer of 8 or 4. ). R4 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, an optionally substituted phenyl group, or an optionally substituted benzyl group. represents a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a hydroxyl group or a halogen atom, and the substituents of the benzyl group are the same or different, 1 to 8 lower alkyl groups, lower haloalkyl groups, lower alkoxy groups or halogen atoms). R6 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. Further, R4 and R6 combine to represent -(CH2)n (here, n represents an integer of 8 or 4). R
6 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkenyloxy group or a lower alkynyloxy group. ] Provided is a plant growth regulator (hereinafter referred to as the plant preparation of the present invention), which is characterized in that it contains the virididine derivative or its salt as an active ingredient.

The compound represented by the general formula (!) is disclosed in JP-A No. 68-990
Manufacturing methods are described in JP-A No. 68, JP-A-68-264478, JP-A-64-88, JP-A-1-52772, and the like. However, these do not describe any use as a plant growth regulator.

The planting preparation of the present invention exhibits ethylene-like activity and can be used, for example, to promote seed germination and to suppress plant height.

Next, Table 1 shows some of the pyrimidine derivatives represented by the general formula (1) that are the active ingredients of the plant preparation of the present invention.

Table 1 R8 When the pyrimidine derivative represented by the general formula (1) is used as an active ingredient of a plant growth regulator, it may be used as it is without adding any other ingredients, but it is usually used in combination with a solid carrier,
It is used by mixing with liquid carriers, surfactants and other formulation auxiliaries to formulate emulsions, permanent agents, suspensions, granules, powders, liquids, etc.

These preparations contain the pyrimidine derivative represented by formula (I) as an active ingredient at a weight ratio of 0. 1-99%, preferably 0. Contains 2 to 95%.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, isopropanol, ethylene glycol, and cellosolve.
Examples include alcohols, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, anionic surfactants such as naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers Examples include nonionic surfactants such as sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester. Examples of formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (isoprobyl acid phosphate), and the like.

These preparations can be used as they are, or diluted with water and sprayed on foliage, or treated with seeds (soaking, etc.). Further, by mixing and using it with other plant growth regulators, it can be expected that the efficacy will be enhanced. In addition, insecticides,
It can also be used in combination with fungicides, nematicides, herbicides, etc.

When the pyrimidine derivative represented by the general formula (I3) is used as an active ingredient of a plant growth regulator, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target plant, etc. 0.05-20 per
09. Preferably 0.1 to 1002, or 0 in terms of concentration
．． 01 to IOOOOppm, preferably 0. 1
~1000ppm. Suspensions, emulsions, wettable powders, etc. are usually processed by diluting a specified amount with water (adding auxiliary agents such as spreading agents, if necessary), and powders, etc. are usually diluted at all. Process it as is.

Examples of the spreading agent include, in addition to the above-mentioned surfactants, polyoxyethylene resin acid (ester) lignin sulfonate, abietate, dinaphthylmethane disulfonate, paraffin, and the like.

Examples Next, the present invention will be explained in more detail by giving formulation examples and test examples.

First, a formulation example will be shown. The compounds are indicated by compound numbers in Table 1, and parts are parts by weight.

Formulation Example 1 50 parts each of Compounds (1) to (148), 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain each permanent agent.

Formulation Example 2 25 parts each of compounds (1) to (148), 8 parts of polyoxyethylene sorbitan monooleate, 8 parts of CMC, and 69 parts of water were mixed and wet-pulverized until the particle size of the active ingredient became 5 microns or less. Obtain each suspension.

Formulation Example 8 Compounds (1) to (148) 2 parts each, kaolin clay 8
8 parts and 10 parts of talc are thoroughly ground and mixed to obtain a powder of each compound.

Formulation Example 4 20 parts each of Compounds (1) to (148), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 60 parts of xylene are thoroughly mixed to obtain each emulsion.

Formulation Example 5 2 parts each of compounds (1) to (148), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of pentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, and water was added and kneaded well. After that, each granule is obtained by granulation and drying.

Next, a test example is shown.

Test Example 1 The test method is “Experimental Biology Course Plant Physiology (I)
A method similar to the yellowed pea test, which is an ethylene bioassay method described in ``Edited by Mitsuyuki Mitsuyuki and Yoshio Masuda, published in 198 full edition'' was used.

Alaska peas were allowed to absorb water overnight at 25° C. in the dark, then sown on paper sheets and grown under the same conditions as above for 8 days. Pea sprouts with approximately 101 hypocotyls were immersed in a 20-ml test solution. Place 10 m of absorbent cotton soaked in water in a cup, and place the treated pea sprouts on the absorbent cotton! Cover the cup and incubate at 25℃ in the dark for 8 hours.
After growing for 1 day, the length and width of the pea epicotyl were measured.

The length of pea epicotyl is 5 compared to untreated pea.
Table 2 shows the concentration (pp m) of the test compound that suppresses the hypocotyl to 0κ and expands the width of the epicotyl to 150κ.

Table 2 Test Example 2 Dimethyl sulfoxide (DMSO) was added to the test compound to give a final concentration of 0.2% and dissolved therein, and water was added thereto to prepare a test solution. Add 1 lettuce seed to the test solution
After soaking for an hour, the seeds were taken out and dried at 80°C.

A Petri dish with a diameter of 90 cm and a height of 20 mm was placed with a piece of paper, 5 rnl of water was added to the paper to moisten the P paper, 50 treated lettuce seeds were drawn on it, and the seeds were grown at 80°C under light conditions. . Germination rate was measured on the 7th day.

The results are shown in Table 8.

For comparison, lettuce seeds treated in the same manner with a 0.2% DMSO aqueous solution were used.

Effects of the invention as shown in Table 8> The planting preparation of the present invention exhibits ethylene-like activity and is used for various purposes such as promoting seed germination and suppressing plant height.

Claims (1)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 represents an alkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxy group (here, the phenyl group The substituents are the same or different and represent 1 to 8 lower alkyl groups, lower haloalkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower alkenyloxy groups, lower alkynyloxy groups, or halogen atoms, and substituents for phenoxy groups. are the same or different 1 to 8 lower alkyl groups, lower haloalkyl groups, lower alkoxy groups, lower haloalkoxy groups,
Represents a lower alkenyloxy group, lower alkynyloxy group, cyano group, nitro group, phenyl group or halogen atom. ). R_2 and R_8 are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a lower haloalkoxy group. Also, R_1 and R_2 are combined to -(CH_2)_m- or -(CH=CH)_
2- (here, m represents an integer of 8 or 4). R_4 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, an optionally substituted phenyl group, or an optionally substituted benzyl group (here, the substituents of the phenyl group are 1 to 8, which are the same or different). lower alkyl groups, lower haloalkyl groups, lower alkoxy groups,
Represents a lower haloalkoxy group, lower alkenyloxy group, lower alkynyloxy group, hydroxyl group or halogen atom, and the substituents of the benzyl group are the same or different;
Represents 1 to 8 lower alkyl groups, lower haloalkyl groups, lower alkoxy groups or halogen atoms. ). R_5
represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. Further, R_4 and R_6 are combined to represent -(CH_2)_n- (here, n represents an integer of 8 or 4). R_6 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkenyloxy group or a lower alkynyloxy group. ] A plant growth regulator comprising a pyrimidine derivative or a salt thereof as an active ingredient.