JPS5859973A - Pyridazinone derivative and its preparation - Google Patents

Abstract

NEW MATERIAL:4-Chloro-5-hydroxy-2-( 3-trifluoromethylphenyl )-3( 2H )pyridazinone. USE:An intermediate for a herbicide (novel substance) of formula II. PROCESS:A compound of formula III is reacted in the presence of an alkali, e.g. NaOH, in a hydrous lower alcohol, e.g. methanol, under heating, and the lower alcohol is then removed. An acid is added to acidify the reaction mixture and remove impurities, and a mineral acid is added to give the compound of formulaI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 4-chloro-5-7-ide 7-2-(
3-)Lifluoromethyl7enyl)-5(2H)pyridazino/and its II method.

The chemical component expressed in the above formula (hereinafter simply referred to as the present feathered compound) is expressed by the 9th formula @: (wherein, water bulk atom, low 9 full medium lj, /%lC2
It is one of the active compounds O'4t1, which is useful as a chemical compound, and is represented by the formula O'4t1, which has a nitro group or a nitro group.

Among the beak compounds of the present invention, the following reaction formula shows a useful new compound @0 development.

Conventionally, the following compounds and their production t& are known as pyridazino/#dichloromethane.

c Kenol Upstock (Ghsg+1cal j
lmtract )@1fa@l59444X#1a) (-00,E,) Xu (wherein, R is 10H,,-cHs-C> or -0)
j, c) 1-C<? :,”) However, it is not known that these known compounds are useful as intermediates for J# steel.

On the other hand, in one compound of the present invention, R of the compound beat is
To have JC's Okira phenyl i warehouse.

It can be an excellent intermediate for weeding steel.

On the other hand, the method for producing the nine compounds of the present invention is shown below using two reaction formulas.

(In the reaction formula, tMrJ is an alkali metal.
Get J. After the end of the reaction, without isolating the intermediate CV),
Anhydrous potassium carbonate 1 to remove lower alcohol and add acid
Mixture of 8y (102 mol) and M,N-dimethylformamide 2o- to 1 liter of 4-methylbearyl chloride
1 t mol was added, heated at 100-110°C for 1 hour with stirring, left to cool, added 100W of water, collected the precipitated crystals, washed with water, air-dried and re-MA from methanol at 14149-150°C. 2.
114 If: Obtained. The yield was 72. The chemical compound shown in Reference Ml (hereinafter simply referred to as the present compound) was used. ) When applied as a herbicide, generally a solid carrier such as clay, talc, bentonite), a solid carrier such as soil, water, flucols (methanol, alcohol, etc.) is used. , aromatic hydrochloride (be/zene, toluene, If7 and 7 fathoms), chlorinated vertical water S, ether fist, and esters (vinegar ether, etc.).

It can be applied by mixing with a liquid carrier such as acid amide # (dimethylformamide 4), if emulsified steel 2 dispersant, clouding agent, penetrating agent, spreading agent! stable M etc. can be added, Liquids, emulsions, irrigation agents.

It can be put to practical use in any desired form such as 9-grain powder.

In addition, other types of herbicides,
It may be applied in combination with each woodcutter insecticide, pesticide, synergist, etc.

Other # single agents for the above species include Gae σ, Weed Koa) a-le-ha/Dopuku (W.J. Ha's qtrolm)
rlibook) HIE' Street Confinement (6
Edition <1977, ), flJ11211 Fuki 8th edition (19
76) and ノ) - Beside No. 1nd Book of
The Feet Bouie/Scientific Op America, $4 Edition.

1979 (Herbicide &ocxb
ook of the weed acc1enc
e80c1ety of au+erica Faw
There is a compound that is distributed in tn m1tion 1979 n.

The next section is the Jt Pass over the heavy f# section.

Formulation example 1 Wettable powder This compound @ (A) 50 parts Sieglite A (trade name) 46 Zheng Norbol 5o
st (surfactant, ] [manufactured by Japanese Chemical Co., Ltd.] 2 parts Carplex (-Surfactant) ! A mixture of s and more is finely ground and used as an irrigation agent. To use K11l, dilute the above hydrating agent with water to a value of 50-90 ntl,
Spray so that the amount of active ingredient is 5 to 1 per 10, OQ・tK.

111 grains ~ This compound (4i g bentonite 501i
Ruri
Mix and crush the mixture uniformly for 42 seconds or more, add 9 bales of water, stir and knead for 1 time, granulate with an extrusion granulator, and dry for 11 L to obtain granules.

In addition, one compound (AJ is agricultural 1 such as upland, mizuide, pot*-)
In addition to the IIK field, it can be used to control various lines 4 in non-agricultural areas such as agricultural fields, vacant lots, and agricultural lands. Time of use.

Although the amount of A may vary depending on the application method, target bookshelf, 1&cultivation w, etc., in general, the amount of active ingredient is 5 to 1.0 per 10 are.
00 is output by the device.

Next, the usefulness of one compound <aows as a herbicide will be specifically examined in the following test examples. ! I will clarify.

Test example 1 Weeding effect test by soil m escaping salt 15 wounds vertically, 2 horizontally
2 pieces of diluvial soil packed in a Puxtec box with a size of 61 cm
t-manpaku, nobie, mehi 7ba, cyperus cyperus, koakaza,
Slippery.

Correct 7tm of leaf clover, doggara, IfJLsa* After soiling, add one active ingredient to the soil so that it is combined with O*j.
Spread it evenly on the surface.

At the time of spraying, θmmFi, *The irrigation agent of the formulation example was diluted with water and sprayed over the entire surface with a small spray. Five weeks after spraying, the herbicidal effect on 811 weeds was evaluated using the following 4tI.
The investigation was carried out in accordance with Ashibu Jun.

&IJKrj1g2 Table shows.

Achievement standard 5...Weed killing 4904 or more (almost completely dead) 4...
・I & Grass 70-90 Nobu 3 --- Killing Akira 40 to 70 Yu 2 -- Acquisition Ak 20-40 1 -- Compensation 5-20 Arrogant 0 -- Weed killing rate S* or less (Almost no effect) However,
The above-mentioned weed killing rate is based on the above-ground growth of the Asahishio district.
The weight of above-ground plants in I & Salt Area O was determined from OwcK below.

1. Soil - Phytotoxicity test on cultivated plants using tin salt Vertical 15-1 Horizontal 221. Depth 6 am O Pufstätter m
li#KII1m Shift Flouvial soil JJt people n, (%
After sowing cotton and wheat at about 15 am and soiling, the active ingredients are thoroughly spread on both the soil and the surface so that the amount of active ingredients is in the prescribed ratio. Application example O: Sprinkle the hydrating agent with water and sprinkle it on the children's picture with the small wrinkles. After 5 times of chemical spraying, chemical damage to the above crops was investigated according to the distribution criteria.

The results are shown in Table 3.

Hanashi Todorobei 5...Saku- has a lot of money withering 4...Jogo against IK is fused 5...F'￥Things are affected by chemical damage 2... l
I The mulberry animal is slightly depressed 1...l
l I can't really relate to the arc...I
I The chemical damage is not visible and the stripes 2 Table 7.
Its active ingredient compound is as shown below.

Iris 3 As is clear from Table IIIA, 9 compounds) are effective in killing 611 weeds, as well as in rice, wheat,
It has no phytotoxic effects on soybeans and cotton, and can be overused in these O-cultivated crops.

Test N3 Weeding effect test under flooded conditions (1) 1
/ 1 (L ＠ ＠ aR O Put the alluvial soil JII in the Neubacher Bot, add the tap water and mix to make the book # 2 am O11 Water Qin.

Japanese millet, Japanese oak, Japanese oak, Japanese firefly, and other nolla roe were mixed in the pots mentioned above, and at the same time, 2.5 tons of rice were transplanted to a depth of T-13. One day later, they were placed on the water surface. JFLt) Add tin salt dropwise to the drug diluent using a graduated pipette to make it 4kM.

At the threshold of 2 weeks after instillation of the drug solution, the effectiveness of the drug against %II drug was investigated according to the published standard of trial 11t11.

Shown in the 4th edition of the 輌米Fi.

Complete set (practice) - Under flooded conditions/) Removal of water
Growing season 41ajilI! 115. Mix alluvial soil in Goo R7L and tap water.

The water depth is 2 wounds and the water conditions are 4 degrees. The above-mentioned woodcutter meeting of Japanese millet, Konagi, Asena, Kikagu-jo, and Homerui were directly sown, and in addition, the violet, water violet, and water violet collected from the multi-flowering weeds in -year-FK! Plant 3, 3, 2, and 2 of JJJL violet, Omodaka clump violet, and Kurogwa clump violet, respectively, during the soil destruction of each Wadafurubot under the above-mentioned flooding conditions.

After 10 days, that is, after the weeds have germinated, dilute the chemical #7 so that the amount of mulberry becomes the specified amount. Drop onto the water surface with a graduated pipette.

After 15 weeks of dropping the lk liquid, the herbicidal effect on each type of weed was investigated in accordance with the published standards of Test 1'1llO.

The results are shown in Table 5.

JIK4 Table: Biralt is a multi-layered herbicide, and its effective component II #II is T1O and 9゜.
Compared to Razon, Sougo towards Ine is not seen at all.
On the other hand, from Table 5, it is clear that the herbicidal Rh effect of the present Kōhaku compound against firefly and its ferns is greater than that of virazolate.

1” 11 Pyrochemical damage test on fence under flood conditions 1/I Q
Fill IOOR's Neuva Wellbot with alluvial soil JII, add water, and mix to create the conditions for flooding the second water lock.

The 2,511th season S (Nipponbare), which had been grown in advance in Kenboku Genshin, was added to 2 each of the above Neubau and Nirbok) K, 5
After transplanting the plants and lowering the diluted flko drug to the water surface at 2 am, the growth status in the gutter was investigated one month later.

A dose of 46 liters of this compound) was carried out in the test plots of 40.20 and 10 tO, respectively.

The results of these O test plots are compared with the Wuxi salt plot.

Although the plant height and number of violets are quite similar to that of other plants, Roll S is not able to follow them at all, so I am confident that there is no chemical damage.

Procedural amendment (spontaneous) 1. Indication of the case Patent Application No. 157265 filed in 1982 2. Name of the invention Pyridazinone derivative and its manufacturing method 5. Relationship with the case Patent applicant address (101) Chiyoda-ku, Tokyo Kanda Nishikicho 5-7-1 (Telephone number: 0474-65-1111)
Contents of amendments to the detailed description of the invention in the specification (1) "Addition of acid" in the last line of page 4 of the specification is corrected to "addition of acetic acid."

(2) [?] on page 8, line 15 of the specification. outn J.

“Corrected to Fourth J.

(3) Delete "rice and" on page 10, line 12 of the specification.

(4) "Tonorflurazo/" in the compound column in Table 2 of Specification Drug 123 and in the "C" row of Table 2 is corrected to "Tonorflurazo/".

(5) #4 In Table 5 on page 15 of the detailed drawing, "Iwanorflurazo/" for the compound - is corrected to "Iwanorflurazo/".

(6) Delete "Omodaka Tuber" in the 14th line, 16th line of the specification.

(7) “Kuroguwa” in line 16 of specification No. 14177L
of.

Corrected to "Kuroguwai".

(8) Compound gI in Table 4 on page 15 of the specification! J411
Correct "nor7razo/" in 1I to "norflurazone."

(9) "Nor7razo/" in the compound column in Table 5 on page 16 of the specification and in the 5th to 6th lines from the bottom of the same page is corrected to "norflurazo/".

Claims (1)

[Claims] 7-2-(A
-)lifluoromethylphenyl)-s(zH)pyridazinone. ψ) The compound represented by the following formula (17:) is heated in the presence of alkali 9D. The water content is heated in an acid alcohol to react. Then, the mineral acid f, #1 is added to form t41 mold.
1): 4-ri a-low 5-no-id mouth 7-2-(
3-)Lifluoromethylphenyl)-3(211) line method of viridazino7.