JPH0592971A - Pyrimidine derivatives and herbicides - Google Patents

Abstract

(57) [Summary] [Purpose] Creation of new herbicides and efficiency improvement of agricultural work by them [Constitution] General formula [I] [Chemical formula 1] (In the formula, R represents a hydrogen atom or a formyl group, and R ¹ and R ² are the same or different and represent a hydrogen atom, a lower alkyl group or a lower alkoxy group.) And a pyrimidine derivative represented by the same as an active ingredient. Herbicide contained. The pyrimidine derivative represented by the general formula [I] exhibits an excellent herbicidal effect with low dose not only on annual weeds in paddy fields and fields but also on perennial weeds, and is safe for crops, particularly useful crops such as soybeans. It is highly likely.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel pyrimidine derivative and a herbicide containing the same as an active ingredient and applicable to paddy fields, upland fields, non-agricultural fields and the like.

[0002]

2. Description of the Related Art Up to now, 2- (pyrimidin-2-yl) oxybenzoic acid ester has been known as a pyrimidine compound having herbicidal activity (JP-A-62-1740).
59 specification). Furthermore, it is described that a 7- (pyrimidin-2-yl) oxyphthalide derivative has herbicidal activity (WO9105781A publication specification).

[0003]

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The herbicidal effect of the compounds described in the specification of the prior art is not necessarily sufficient. The present inventors have conducted extensive studies on pyrimidine-based compounds for the purpose of developing further improved compounds, and as a result, the pyrimidine derivative of the present invention in which the 7-position atom of the pyrimidine nucleus and phthalide are bonded with nitrogen is an annual weed. The present invention has been completed based on the finding that it exhibits excellent herbicidal effects not only on perennial weeds but also on the safety of crops, especially useful crops such as soybeans.

The pyrimidine derivative of the present invention has the general formula [I]

[0004]

[Chemical 2]

(In the formula, R represents a hydrogen atom or a formyl group, and R ¹ and R ² are the same or different and represent a hydrogen atom, a lower alkyl group or a lower alkoxy group.). Here, as the lower alkyl group, methyl, ethyl,
Propyl and butyl can be mentioned. Further, examples of the lower alkoxy group include methoxy, ethoxy, propoxy, and butoxy.

Next, Table 1 shows specific examples of the compound represented by the general formula [I]. The compound numbers are referred to in the description below.

[0007]

[Table 1]

The compound of the present invention can be produced according to the following methods, but is not limited to these methods.

[0009]

[Reaction formula 1] (In the formula, R, R ¹ and R ² have the same meanings as described above, and L represents a leaving group.)

The compound [I] comprises a phthalide derivative represented by the general formula [II] and a pyrimidine derivative represented by the general formula [III] in an inert solvent at a temperature from room temperature to the boiling point of the solvent. It can be produced by reacting in the presence.

Examples of the leaving group include methanesulfonyl group, chlorine and the like. As the base used herein, for example, alkali metal or alkaline earth metal, especially sodium and potassium and magnesium and calcium carbonates, hydrogen carbonates, acetates, alcoholates, hydroxides, hydrides or oxides, etc. Can be used. Furthermore, it is also possible to use organic bases, for example tertiary amines such as pyridine or triethylamine. Examples of the solvent include hydrocarbon solvents such as toluene, benzene and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol and ethanol, ethyl ether, isopropyl ether, tetrahydrofuran, 1 Ether solvents such as 1,4-dioxane, N, N-dimethylformamide, N,
An aprotic polar solvent such as N-dimethylacetamide or dimethyl sulfoxide, or an ester solvent such as ethyl acetate can be used. A preferred combination of solvent and base is a reaction using potassium carbonate or sodium hydride in a N, N-dimethylformamide or tetrahydrofuran solvent.

In the phthalide derivative represented by the general formula [II], the compound in which R is a hydrogen atom has a known structure and its production method (Pharmaceutical Journal, Vol. 73, p. 526 (1953).
Year)). A compound in which R is a formyl group is R
It can be produced by reacting a compound in which is a hydrogen atom with formic acid.

[0013]

EXAMPLES Next, the production method of the compound of the present invention will be specifically described with reference to Reference Examples and Examples. Reference Example Synthesis of 7-formamido-3-methylphthalide 3.50 g (0.021) of 7-amino-3-methylphthalide
(5 mol) was heated to reflux in 30 ml of formic acid for 2 hours. After distilling off excess formic acid, water was added and the mixture was extracted with dichloromethane, washed with 10% aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the formed crystals were washed with isopropyl ether and 7.40 g of 7-formamido-3-methylphthalide.
(Yield 83%) was obtained as colorless crystals. Melting point: 111-
116 ° C.

Example 7- [N-formyl-N- (4,6-dimethoxypyrimidin-2-yl) amino] -3-methylphthalide (Compound 2) 1.78 g (9. 7) of formamide-3-methylphthalide
3 mmol) was dissolved in 60 ml of N, N-dimethylformamide and 0.41 g (10.%) of sodium hydride (60% oily).
2 mmol) was added and stirred for 30 minutes, and then 2.23 g (10.2 m) of 2-methanesulfonyl-4,6-dimethoxypyrimidine.
mol) was added and stirred for 6 hours. Ice water was added, the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained mixture was separated and purified by column chromatography (Wakogel C-300, ethyl acetate / n-hexane (1: 3) to obtain the desired product 7
-[N-formyl-N- (4,6-dimethoxypyrimidin-2-yl) amino] -3-methylphthalide 0.77 g
(Yield 25%) was obtained as colorless crystals. Melting point: 159-
164 ° C.

The herbicide of the present invention comprises a pyrimidine derivative represented by the general formula [I] as an active ingredient. To use the compound of the present invention as a herbicide, the compound of the present invention may be used by itself, but a carrier generally used for formulation, a surfactant, a dispersant or an auxiliary agent, etc. is blended to prepare a powder, It can also be used by formulating it into a wettable powder, an emulsion, a fine granule or a granule.

The carrier used for formulation is
For example Sieglite, talc, bentonite, clay,
Examples thereof include solid carriers such as kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane and methylnaphthalene.

Examples of the surfactants and dispersants include alkylbenzene sulfonic acid metal salts, dinaphthylmethane disulfonic acid metal salts, alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, and polyoxyethylene glycol ethers. Examples thereof include oxyethylene alkyl aryl ether and polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like. When using, dilute to an appropriate concentration and spray or apply directly.

The herbicide of the present invention can be used by foliage application, soil application or water surface application. The blending ratio of the active ingredient is appropriately selected according to need, but in the case of powder or granule, it is appropriately selected from the range of 0.01 to 10% (weight), preferably 0.05 to 5% (weight). Is good. When used as an emulsion or wettable powder, 1-50%
(Weight), preferably 5 to 20% (weight).

The application rate of the herbicide of the present invention varies depending on the kind of compound used, target weeds, development tendency, environmental conditions and dosage form to be used, but when it is used as it is as in powders and granules, The active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When it is used in a liquid state such as an emulsion or a wettable powder, it is appropriately selected from the range of 0.1 to 50,000 ppm, preferably 10 to 10,000 ppm.

If desired, the compound of the present invention may be mixed with insecticides, fungicides, other herbicides, plant growth regulators, fertilizers and the like. Next, the formulation method will be specifically described with reference to typical formulation examples. The types and compounding ratios of the compounds and additives are not limited to these, and can be changed in a wide range. In the following description, “part” means part by weight.

Formulation Example 1 Wettable powder 10 parts of compound (2), 0.5 parts of Emulgen (registered trademark of Kao Corporation) 810, 0.5 parts of demol (registered trademark of Kao Corporation) N, Kunilite 20 parts of (registered trademark of Kunimine Industry Co., Ltd.) 201 and 69 parts of Sieglite (registered trademark of Sieglite Co., Ltd.) CA are mixed and pulverized to obtain a wettable powder.

Formulation Example 2 Wettable powder 0.5 parts of Emulgen 810 in 10 parts of compound (1),
A wettable powder is obtained by mixing and pulverizing 0.5 part of Demol N, 20 parts of Kunilite 201, 5 parts of Carplex 80, and 64 parts of Sieglite CA.

Formulation Example 3 Wettable powder 0.5 parts of Demol N to 10 parts of Compound (3) and 0.5 parts of Emar (registered trademark of Kao Atlas Co., Ltd.) 10
Parts, 20 parts of Kunilite 301, 5 parts of Carplex 80, and 64 parts of calcium carbonate are mixed and pulverized to obtain a wettable powder.

Formulation Example 4 Emulsion To 10 parts of Compound (4) were added 80 parts of an equal mixture of xylene and isophorone, and 10 parts of surfactant Solpol (registered trademark of Toho Chemical Industry Co., Ltd.) 800A, and these were mixed well. To obtain an emulsion.

Formulation Example 5 Granules 3 parts of the compound (3), 77 parts of an extender in which talc and bentonite are mixed at a ratio of 1: 3, and 5 parts of white carbon.
Part, 5 parts of surfactant Solpol 800A, 10 parts of water was added and kneaded well to form a paste, and the diameter was 0.7 mm.
After being extruded through the sieving hole of No. 1 and dried, it is cut into a length of 0.5 to 1 mm to obtain granules.

[0026]

INDUSTRIAL APPLICABILITY The compound of the present invention represented by the general formula [I] is a variety of weeds which are problematic in the field, such as, for example, Aedes aegypti, Aoubiyu, Shiroza, chickweed, hornbill, American stag deer, American hornwort, Asagao and Onamomi. Such as broad-leaved weeds, perennial and first-year cyperaceae weeds such as pearl nutsedges, yellow sedges, medusa, cyperaceae, sycamore, etc. It exhibits an excellent herbicidal effect over a wide range of growing season. In addition, Taenubiya, Tamagayatsu, which occur in paddy fields,
It is also possible to control annual weeds such as eels and perennial weeds such as Urikawa, Omodaka, Cyperus japonicus, Kurogwai, Firefly and Heraomodaka. On the other hand, the herbicide of the present invention is highly safe for crops, and particularly, highly safe for rice, wheat, barley, corn, grain sorghum, soybean, cotton, sugar beet and the like.

Next, the effects of the compound of the present invention will be described with reference to test examples. Test Example 1 (Herbicidal effect test by treatment of upland soil) A 120 cm ² plastic pot was filled with upland soil, and edible millet (Ec), giant sardine (Po), aubiyu (Am), white azalea
(Ch) and Kogomegayatsuri (Ci) were seeded and covered with soil. A wettable powder prepared according to Formulation Example 1 was diluted with water, and 1
100 l per 10 ares was sprayed uniformly on the soil surface with a small sprayer so that the active ingredient was 100 g per 0 ares. Then, it was grown in a greenhouse, and the herbicidal effect was investigated on the 21st day of the treatment according to the criteria in Table 2. The results are shown in Table 3.

[0028]

[Table 2]

[0029]

[Table 3]

Test Example 2 (Herbicidal effect test by foliar treatment of upland field) A 120 cm ² plastic pot was filled with upland field soil, and edible millet (Ec), Stinkweed (Po), Aubiyu (Am), Shiroza
(Ch), Kogomegayatsuri (Ci) various seeds are sowed and grown in a greenhouse for 2 weeks, and then the wettable powder prepared according to Formulation Example 1 is diluted with water so that the active ingredient becomes 100 g per 10 ares. In addition, 100 liters per 10 ares were foliar-sprayed over the whole plant with a small sprayer. Then, it was grown in a greenhouse, and the herbicidal effect was investigated on the 14th day of treatment according to the criteria in Table 2. The results are shown in Table 4.

[0031]

[Table 4]

Test Example 3 (Crop Selectivity Test by Treatment of Upland Soil) A 600 cm ² plastic pot was filled with upland soil, and soybean (Gl), cotton (Go), edible grass (Ec), Johnson grass (S
Various seedlings of o), Nosumenotepou (Al), Stinkweed (Po), Aubiyu (Am), and Shiroza (Ch) were sown and covered with soil.
The next day, the prescribed amount of active ingredient (ai, g / 10a) of the wettable powder prepared according to Formulation Example 1 was diluted with water to give 100 l per 10 are.
Was sprayed uniformly on the soil surface with a small sprayer. Then, it was grown in a greenhouse, and 21 days after the treatment, the herbicidal effect was investigated according to the criteria shown in Table 2. The test results are shown in Table 5.

[0033]

[Table 5]

[0034]

 ─────────────────────────────────────────────────── --- Continuation of the front page (72) Inventor Shigehiko Tachikawa 3-57 Anzai, Shizuoka City, Shizuoka Prefecture (72) Inventor Takeshige Miyazawa 9 out of 1205 Iwaname, Daito Town, Ogasa County, Shizuoka Prefecture

Claims (2)

[Claims] 1. A general formula: (In the formula, R represents a hydrogen atom or a formyl group, and R ¹ and R ² are the same or different and represent a hydrogen atom, a lower alkyl group or a lower alkoxy group.). 2. A herbicide containing the pyrimidine derivative according to claim 1 as an active ingredient.