JPS5872563A - N-phenyltetrahydrophthalmide derivative, its preparation, and herbicide containing it as active ingredient - Google Patents

Abstract

NEW MATERIAL:An N-phenyltetrahydrophthalimide derivative shown by the formulaI(R is 5-8C alkyl). EXAMPLE:N-(4-Chloro-2-fluoro-5-n-amyloxyphenyl)-3,4,5,6-tetrahydrophth alimide. USE:A herbicide showing high activity by upland foliar treatment, having improved selectivity for maize and soybean, exhibiting improved herbicidal power to weeds in a paddy field by its small amount, having low phytotoxicity to paddy-rice plant. PROCESS:An aniline derivative shown by the formula II is reacted with 3,4,5,6- tetrahydrophthalic anhydride shown by the formula V or an N-phenyltetraphthalimide derivative shown by the formula III (M is alkali metal) is reacted with a halogen compound shown by the formula IV (X is halogen) to give a compound shown by the formulaI.

Description

[Detailed Description of the Invention] RO (J [wherein RFi represents an alkyl group having a carbon number of s-r]] N-7 engineering nyltetrahydride qphthalic acid derivative, its production method, and its use as an active ingredient Q: The present inventors have found that 1M-phenyltetrahydro-7-talimide derivatives have excellent herbicidal efficacy!i:@L, soybean, rice, corn,
We have continued research into herbicides that are less harmful to wheat and other overlapping crops, are effective at low doses, and have little impact on the natural environment.0
As a result, the compound group represented by the general formula (I) has excellent weight-removal activity at an extremely low dose in field foliage treatment, and has selectivity for overlapping crops such as corn and soybeans. When used as a herbicide for rice fields and paddy fields, it was discovered that it exhibits excellent herbicidal power even at low doses, and that it has excellent properties such that no chemical damage to rice is observed.The present invention was completed. More specifically, the compounds of the present invention exhibit high activity when used in field foliar treatments, and are effective against butilon thsophrasti, a problem weed in corn or soybean fields. (1ielianthus annuus), Chi■
Tsutona! Gao (Datura stramonium)
), v Aba 7 Saga
rea), Onamol (Xantk41um str
umarium), Jlolanum
In addition, when the compound of the present invention is used in paddy fields, it can be used to control grasshoppers (Japanese millet), etc. at low doses, and sometimes shows poor selectivity for corn or soybeans. - Problems with pine needles and silver grass that are not only effective against grasses - Single 11c - Attractive, but less harmful to water 11 j/-1/
1-(Dark-1-cofluorophenyl)-J, Tei, J, 4-tetra described in Publication No. 12/2012 was mixed with do-O7 talimide (comparative compound), but as shown in the examples given below, The compounds of the present invention exhibit significantly higher efficacy in the treatment of corn and soybeans, and have excellent selectivity for corn and soybeans. It was highly effective against perennial weeds such as the grass and grass, and was able to control comparative compounds and other weeds at low doses. The safety against rice was also superior to that of the comparative compound.

The compound of the present invention represented in the general formula has the following reaction formula (&)
and (0(1) synthesized by the reaction shown in (9)
(I) [In the formula, R is as defined above], x is a /10 gene atom, and 1M is an alkali metal atom.] In reaction (1), the aniline derivative (amount) and 1°41t, j, 4-tetrahydrophthalic anhydride in the presence of an inert solvent such as vinegar*. In reaction (b), acetonitrile, dimethy/θθ
The reaction is preferably carried out at a temperature of 60°C to 10°C.◇ When the compound of the present invention is used, the active substance itself may be sprayed, or granules, wettable powders, emulsions, etc. Any formulation form can be used.In preparing our formulations, we use solid carriers such as mineral powders (
Kaolin.

bentonite, clay, q! talcum, talc,
quartzite, mica, quartzite, stone oxide calcium, alumite, etc.), vegetable powder* (dai! powder, wheat flour, wood flour, taba: lI), starch, crystalline rose, etc. )
, polymer compounds (petroleum 11f&, polycyclized vinyl, danmaruga^, ketone tree 1ml, further alumina, lyl)
I can open all the boxes.

As a liquid carrier, for example, Alney J&1I4
(Methylfuror, ethyl alcohol.

(ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xyrelene, methylnaphthalene, etc.), chlorinated expanded hydrogen III (chloroform, carbon tetrachloride, monochlorobenzene, etc.), ether II (dioxane, tetrahydroplast, etc.) Lofuran, etc.) S Keto 21m (acetone, methyl ethyl ketone, cyclohexanone, etc.).

Ester * (Vinegar enal, acetic acid butyl ester.

(ethylene glycol acetate, etc.), acid-hardened steel (dimethylformamide, etc.), 7M! ) Nitrile, ethylene glycol ethyl ether.

Water, etc. can be removed.Surfactants used for the purpose of emulsification, dispersion, and spreading can be nonionic, ionizable, cationic, or amphoteric. Examples of surfactants include polyoxyethylene furkyl ether, polyoxyethylene alkyl heptadyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, oxyethylene oxypropylene polymer, and polyoxyethylene rubitan fatty acid. Ester, polydiethylene flukyrin deesterified, fatty acid salt, alkyl sulfate ester salt, furkylsulfinate, alkyl 7
These include lylsulfur hydrate, furkyl phosphate ester salt, polyethylene ethylene a, alkyl sulfate ester, quaternary ammonium salt, etc., but of course only these are @determined tL.
In addition, for these purposes, gelatin, near-J zein, fulginate, starch, and *ten are required according to the 4PK.

Polyvinyl alcohol and the like can be used as adjuvants.Also, the active ingredients in the formulation are not included! It can be prepared in various proportions up to 0.
lallk**/p~t.

When applied, &i: exerts grass effect and reduces its own weight.
Examples of formulations of this herbicide are shown below.

Formulation Example / Compound (1) 7 parts by weight of J, 5 parts by weight of P-derelbenzene sulfonate, parts by weight of lignin sulfuric acid, J and ±70 parts by weight of diatoms were thoroughly ground and mixed to form a wettable powder. Got it.

Combination? Ii,, 2 Compound (J) J Oml parts, emulsifier Tsurupol obtained. Formulation example J Compound (/Jjllt parts, white carbon 7 parts by weight,
Part by weight of lignin sulfurinate J and 1 part by weight of clay are thoroughly pulverized and mixed, water is added, kneaded, and then granulated and dried to obtain granules.

Arrangement example D Compound 4214I weight s% 7 weight parts of inpropyl phosphate, clay 4j11 weight S and tal 930 weight parts are thoroughly ground and warmed to obtain a powder 〇 Formulation example! Bentonite da θjukurabe, lignin sull carn, salt! Grind and mix parts by weight and clay 11 parts, add water, l#
M granulation is dried to obtain granules containing no active ingredient. 95 parts by weight of the granules are impregnated with 5 parts by weight of the compound (Kura) to obtain granules. Formulation Example 6 Compound (20 parts by weight of A is added to 5 parts by weight of oxyethylene sorbitan monolactate was mixed with 60 parts by weight of an aqueous solution, wet-pulverized until the particle size of the active ingredient was 3μ or less, and 20 parts by weight of an aqueous solution containing sodium alginate J weight bag as a dispersion stabilizer. To mix K, L
Obtain parts by weight of a cloudy preparation lθθ.

In order to improve the efficacy of the compound of the present invention as a herbicide,
It is possible to mix it with other herbicides.

In some cases, a synergistic effect may be expected. ◎An example of this is 1,*-jikupurphenoxy vinegar #; comethyl-darchlorphenoxy vinegar.
, including salts), r-(2-methyldacroJ&7!
Niruda'-nitrophenyl ether, such as butyric acid;
Ko, 4I.

6-Dolichlorphenyluda'-nitrophenyl ether; j-methylphenyl-q'-nitrophenyl ether i-2-l-diq. Lufeniruda Nitro J'
-methoxyphenyl ether; ) tJ7 dine methylthioda, 6-bis-inpropylamino-/eJ
J
, j-1su7jin, etc.) u7 D: / system # single agent, 3
-(J, goudichlorphenyl)-/,/-limethylure7' i J -(J.

chlorphenyl)-7-nodochyle-l-methylurea;
cI methylthiophenyl)-i,/-dimethylurea;
/-(-1phenylbuvir)-J-(<7-methylphenyl)urea;lid-("xa-dimethylureal)
-Fuki'-(4I-methylphenyl>was urea-based herbicide, isopropyl M-(J-chlorophenyl)carbamate; methyl 舅-<s,e-dichlorophenyl)carbamate and other carbamate-based herbicides *L B - (t,-chlorobenzyl)-N,w-jethylthiolcarbamate; 8-methyA-H,M-heki! Thiol carbamate weight removing agent such as methylenethiol carbamate, 3
．． Dirjkrolp. Pionanilide 6N-methoxylemethyl-94-pmethyl-chlor7%')anilide;
-1-ru-11, 6-ethyl-H-(butoxymethyl)-7cetanilide → rolacetyl-M-C2,t
, -diethyl & 7 z nyl) glycine ethyl ester 5
Commercially available amide herbicides such as N-(a,g-dimethinebenzyl)-α-bromtert-butylacetamide,! -bromo-3-secanglyptyl-6-methyluracil;
J-cyclohexyl-j, uracil-based defrosting agents of the tri-rimethylene uralel group, /, /'-dimethyl-41, goo bisviridinium dichloride, etc., lysinium salt-based defrosting agents, M, N -bis(phoscarzmethyl)crylene; 〇-ethyl 0-(-1-nidro-j-methylphenyl)M-secondary-butyl methoxyl dothioate; 5-(a-methyl-7-piperidylcarbonylmethyl)0. Phosphorus herbicides such as 0-dipropylphos-kiguchidiothate; o-methyl o-(cornitroder methylphenyl) y-intulovir kiloamidothionate
``j''#''-) Refluroo.

6-Sinitro M, N-dibuqvir-1)-) Toluidine herbicide of Luidine group, j-t・rt-butyl-J-
(K,4!-dichloroj-inpropoxyphenyl)
/ s Ja 41-O-teisu diazoline-on; 3-Improv and Roux/H-J.

/, 3-Benzothiadiazin-(b)-jl-one-1,-1 dioxiledo; α-(β-naphthocyle)propion 7nilide λ-(a-su7tokyle)-father, father-diethylpropion 71L doi J, J'-dimethyl-dermethoxybenzophenone 114 ((,,2e 41-dichlorobenzoyl)-/, J-dimethylpyrazole-j
The herbicide of the present invention can also be used as a fungicide or a microbial pesticide.

It is also possible to use it in combination with Viresqoid insecticides, other insecticides, plant growth regulators, and fertilizer capes. 4I-crototofluoroq-, ￥1 I-fluorokylephenyl)〒3. Da! , 4-tetrakl'lophthalai-tailed irises-(II-chloro-2-fluoro-!-Hirodoroxy7
! 2A) -J, da, j, 6-chitrahyF loftalimide λ, dejf was concentrated in DM sea θd, potassium carbonate 7.
Add 6F and further add ys-73L Lubu0 Midoha 4jI. Stir this at 70-10°C for 3 hours. Add water to the reaction solution and extract with ether. Wash the ether layer with water, dry, concentrate, The residue was purified by silica gel chromatography and θ,! Obtained crystals of JP o mp /
(X).
, j , 4-tetrahydrophthafreimide was confirmed to be O. The compound shown in Table 7 was synthesized in exactly the same manner as in Example 1, and the compound shown in Table 7 was synthesized in Example 9 (Paddy-like pre-emergence soil treatment test). //1000
After filling a Wagner pot with soil and flooding it with water, rice of the 311th season was transplanted, and then quince millet, grasshopper, and broad-leaved weeds were planted.

It is 90 times to plant seeds of Pinus cabbage and Tsu U cuff with 9 Fi stems! At the time when each of the sunflower weeds started to germinate, a predetermined amount of the active substance was made into an emulsion and applied to the water surface Km below the water surface. drug store jlj week a
We investigated the effectiveness of KWk cars and rice chemical damage, and here are the results! The evaluation of herbicidal efficacy was expressed as a number from 0 to j as shown below, and rice damage was also expressed using the same criteria as the herbicidal efficacy.

0...Weed suppression rate O~q%/...I 10~-9% -...l J 0~#tsu Arrogant J...
#j0~4te 悌q...l 70~l? vomit...I
ta ρ, ~10 θg - Table comparison compound (2) M- (1-ri cIo-, 2-fluoro ρ) linyl) - J e I * j # b ! r
9* vIQ Futarui ANk softening house *91) Jt
41. s-to u9aa7g=Rule l'-Nitrov-winged diyl ether Example J (Upland field post-germination foliage treatment) Vertical j j cyt s Horizontal-j on e Size/θ
Fill α plastic trays with field soil and grow corn, soybeans, Japanese crocodile, sunflowers, Japanese morning glory,
Malva morning glory, Onamomi.

Sow brilliance and hackberry.

After growing in a greenhouse for a week, arrange one of these trays in a frame with vertical jθell*horizontal/θθ scratches and height of 410em, and apply a predetermined amount of each chemical to the entire frame using a light snow sprayer from above the plant. After spraying one of the chemicals on the stems and growing them in the cylinder chamber for 3 weeks, each plant was evaluated for herbicidal damage or herbicidal efficacy as in Example - θ'~! Review 1 [iK? Investigate nine.
The results are shown in Table j113.The processing chemicals are shown in Example 3.
using an emulsion made according to the recipe.

Water containing a spreading agent and emulsified runners were tested.B The size of the plants at the time of drug treatment depends on the species, but the plant height was - - - - ρ at the Habomoto II/~5lllr stage.・ 3rd table 瑠鑒翰翛 yoke c) 2-ri old toder (ethylamino) -
b-(Impropyl 7mino)-8-triazine ratio 1 day - (2) J-Impropyl-J # / # J
-penbutifuji 1 dinone-←)-2,J-cyoxide

Claims (1)

[Scope of Claims] H) An M-Phenyltetra dolphthalide conductor represented by the general formula [wherein R represents an alkyl group having a carbon number of j-f] - General formula [wherein R is 7-niline derivative represented by ◎] and J, 41. N-7-tetrahydrophthalic ILPI represented by the general formula [wherein R is as described above], which is reacted with J,4-tetrahydrophthalic anhydride.
Manufacturing method of I conductor◎ (support) General formula [In the formula, R represents an alkyl group having from j to g carbon atoms, and X represents a halogen atom. ] A general formula [wherein the percentage image is obtained by reacting a halogen compound represented by the formula [in the formula, 1M is 0] which narrows the alkali metal atom with a 7-7-functional nyltetrahydro phthalyl ILPII conductor] R is as defined above. 0] A method for producing an N-phenyltetrahydro-7-talimide derivative. ←) General formula [In the formula, R is Iwa prime number! ~l represents an alkyl group. ] A herbicide containing the M-phenyltetrahyNOphthalene IP derivative shown as an active ingredient.