JPS5946272A - Pyrazole derivative, its preparation and selective herbicide containing said derivative - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [A is lower alkyl; Z is thiophene, benzothiophene, pyridine, quinoline, isoxazole, benzoxazole, uracil, pyrimidine, 1,3,4-thiadiazolone, 1,3,5-triazine, oxazole, 1,2,3-benzotriazin-4-one, benzoxazolone, benzimidazole, benzofuran, pyrazine, delta-pyrone, coumarin, indole, pyrrole, furan, or naphthalene which may have 1-3 substituent groups (lower alkyl, lower alkoxy, halogen, NO2, NH2, phenyl, phenoxy or CF3)]. EXAMPLE:4-(2,4-Dichlorobenzoyl)-1-methyl-5-(2-pyridylmethoxy)pyrazole. USE:Selective herbicide. PROCESS:The compound of formula I can be prepared by reacting the compound of formula II with the compound of formula III (Hal is halogen).

Description

Detailed Description of the Invention The present invention relates to the general formula (1);
, 1 naosoene, pencinasufene, pyridine, quinoline, inogizazole, benzoxazole.

uracil, pyrimidine, 1,6.4-nadiazole,
1,5.5-1・Riryojin, Ogizazol, 1,2゜6
-Benfu°l Suγjin-4-on, Benn°oky-
Resolone, benzimidazo-/L, benzofuran.

Pyrazine, σ-pyrone, coumarin, inl.

Virol, 7 Lan-T Moon-Tsu 7 Talen) Shows 1 Ltc aromatic soil. 1μ, these aromatic rings are lower argyl groups, lower alkoxy groups, halogen groups,
-o group, amino group, noenyl group, noenoxy group' may be directly substituted with 1 to 3 selected substituents from the group A of the Menal group of the order Trinorrhoeae. ) in Iwasa Sairu Villan'-le Af5! , i+ +, h, -tbi) manufacturing method and the 1st draw of the Shijin tai - or tyo 2nd draw or more? L-Minami-Selection 1ε1 mi-removal 41-Agent CC included as subsidy.

The pyrazole compound (hereinafter referred to as 1-', A) that is expressed in formula (1) above is referred to as an invention compound. H:j',
It is useful as a herbicide compound that whitens weeds and kills them. Even in the case of 12, it has a strong herbicidal power with an extremely small amount of h1 application.

Conventionally, pyrazole u L"1.14-t:1'
, a large number of compounds are known, and among these (1),
A commercially available herbicide for paddy fields is bifusolate (-, several names), which is represented by the following structural formula: ftl'.

On the other hand, in addition to Pyrazole, there are many other herbicides that have been put into practical use.

It is generally widely used as a single agent and a mixed agent. [,, J. However, perennials that occur in water 10 [are generally grown at 111. It's a big deal and it's also happening
The song is also great for pest control.
There are many effective weed control A11, perennial d'
4h weed number' (highly effective -1 herbicide vt, c'; T current situation is not so good - C Aotsu).

In addition, due to the establishment of water for the first time (11 "i cultivation", "hijin" of Shindanka, and early transplanting time), the conditions are favorable for Shiba generation 1, and one time Weeding and weeding treatment is the best way to completely control weeds and perennial weeds.

In recent years, in Mokomi 1
By spraying 1124 cross-reagents, all miscellaneous leather (L-all T) (attempts to control are divine single agents or mixtures of fc, it, and f)
t, but the herbicidal effects V and I are extremely small and sufficient1), (
- Therefore, it is impossible to process VC only once - C young fruit! j
6 in case 1.1 Qi 1ik; drop system ml per area
This will contribute to the total cost.

In order to solve this problem, the emergence of a one-time treatment herbicide with extremely low permeability and a wide range of efficiencies is eagerly awaited. is the current situation.

As a result of the inventors' repeated persimmon tests, it has been shown to be effective against a wide range of weeds, and among these 71 weeds,
Conventionally, effective herbicides such as 1εJj (Qlil-C) and other effective herbicides have a high virility 11. This discovery led to the completion of the present invention.

In addition, the two compounds of the present invention, cL, have no phytotoxicity to water 411, and can be used safely for one period of time.

The compound of the present invention has the general formula (1) as shown below: (In the formula, A and Z have the same meaning as 'E + iil nt'j.

) It is a pyrazole compound represented by It is to be.

Conventionally, several compounds have been known for herbicidal viscosity or -H- bifusol, including those disclosed in Japanese Patent Publication No. 54-56648 and Japanese Patent Application Laid-Open No. 54-41872.
-) J Publication VCit 4--1 contains information on herbicides, and it is stated that they are for commercial use.

It was put into practical use as pyrazole MMm by Tono et al.

The only commercially available σ7L is Bifsolet-1 (-several names) represented by the above-mentioned compound A.

JP-A No. 11 (J 54-41872)
&J', , 6-positions of the pyrazole of the compound represented by formula (1) are all 1, and Qr (extension) is the only group.

1ft, pyrazole IJ5 helmet listed in the above tBt Publication No. 54-56648 bow bulletin, IF tl:
, expressed by the above formula (1) is 7'1. , :, Compound 1. /
) The 6th position of L nirazole is mostly a lower alkyl group.
(: Yes, 51) The substituent of γ is r))], SH, the salt of Nisdel-C, and the isoic acid of Nisdel-C. In ξ, if the 6th position is a hydrogen atom, f1 below Vc
As shown, - only examples are real bi! A specific VC is listed in one column.

(1, This compound 13 f, "L + upper 11 dino? 14 Publication 1 #154-6664 No. However, the herbicidal activity is inferior even if the herbicidal activity is inferior. 4) Motoakina et al. It was confirmed that the compound had much better herbicidal viscosity.

- Still, JP-A-57-11979 describes a pyrazole compound that is described in the general formula of nen, which is an extremely broad concept that also encompasses the compound of the present invention, but this publication
- Kozue Mori and one exemplified compound -)! , Example QC
The compound listed above is expressed by the formula (1)
], all of the 6-positions of the compounds are lower γ-alkyl groups, and the compounds 11. I Z group is only an imide group, and for one compound of the present invention, t, 1. Specifically, Q1 has not been disclosed at all. Ministry of the Invention et al.
Prior to the publication of the above publication, the compound of the present invention, in which the 3rd position of ribirazole is a hydrogen atom, had been extensively tested, and as mentioned above, the patent &'C
&1 The compound of the present invention is.

It is not specifically stated at all.

Sota 1 Invention 1 Co et al Vl, the above publication VC specifically disclosed compounds, especially as examples, n'fL compound i / (for weeding r1'', i 1% Hλ; try the pass Taka, previous 6] Commercially available compound A P (-Comparison-C, P,
``It was confirmed that the balance was weak.'' In other words, it was found that the weight removal activity of Compound 1 of the present invention was very inferior to that of VC.

A large number of pyrazole M''j 'N groups have been synthesized
A herbicidal activity test was not conducted (although 511t in the pyrazole term was always a hydrogen atom -C only for compound B, which is a compound before df).

1', 61', k (°fThe direct chivalry base of Rukiruji temple 7-]-) f-A'Q'll (3h
't: -r Ruki A6) 5Ut storage) 13: r Synthesis is relatively easy /, but 3 11 is 71 (in the case of elementary atoms, the synthesis of - is very difficult (difficult) What happened and the 3rd place Argyl visit exclusive V (compared to the herbicidal activity is low and practical (/l: If (poor thing VC, 'J',
I was talking about 4.

Invention of the present invention 1. Regarding the compound in which the 6th position of pyrazole 4jJ is a hydrogen atom, as a result of 4!11 discussions, we found that it is easy to synthesize (2444) 'l-1k V+', lIi l
-, MLIL 5 (>7J') bf candidate part, also the lottery 84 fr closure mentioned above - clothing style (11-C six wasa waza waza pu present invention 1 compound is 4'6 different strong fr,棧-tI'
L force is good, and water tiii k ('phantom safety 1
It was also discovered that the fcl live bait is extremely effective as a herbicide for water A+I'+.

Missing ((, + invention compound rJ, -F 9 in the reaction formula of 114
E is easily synthesized.

(stomach)
(0) 11゜(1) (In the formula,) 11 halogen atom-ma'tC,a water brewing sample ゎ1,, lla ゎ represents halogen 1. Also, A and Zl have the same dry taste as above. ) ff reaction formula (1) was used, 4-carboethoxy-5-human 1-methylpyrazole was synthesized using hydroxymenalemmalone 1 antiester and methylhydrazine as raw materials, and then hydrolyzed and decarboxylated. The intermediate (l) of the six-part compound is a new LL compound, and the compound (1) is a new LL compound.
Using f) as a raw material, it can be synthesized according to reaction formula (2). - Examples include chemical dehydrogenation agents (nozomakuge, sulfur hydroxide,
In the presence of water (Hikariu A, 19ium carbonate, triethylamine),
In a bath medium, react Iy with 2,4-TsukuIJ/l benzene-Nb hydride to form -C ester, and form ester? r: turn 11
N: let (b) be obtained 6゜esterified non 1c, 1 of .
1. Rose and 1. So, in terms of dioxane, acetyl nitrile, benzene, toluene, chloro;
-Used in 4) can of course be tJ/I)
, 1-luene, water-chloroporum ray 11 system can also be used in combination with 4 phase transfer catalysts.

Reaction formula (3) shows a reaction in which the compound (1) of the present invention is obtained by combining an intermediate moiety, a halogen tM, and a specific aromatic cyclization compound containing a substituted lower argyl group fM.

This reaction is carried out using an inert bath medium (f/1, for example, diene ether, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, aromatic hydrocarbons H, -r7ton, ketones such as methyl ethyl ketone, dichloromethane.

chloroporum, carbon tetrachloride, etc.) halogenated hydrocarbons, acetic acid enal, N, 14-dinotylpolamide,
Acetonitrile (can be used twice). Dehydrohalogenation Ha11 (tllJ-ege, thorium carbonate, inorganic bases of potassium carbonate, pyridine, trienalamine,
11, LJ-diethylaniline, etc. '14' (Residual salt! L!: etc.) is present under 1! Is it something you should do? From room temperature to room temperature, Jt
Between the boiling point of the liquid and the boiling point of the liquefied liquid, the boiling point of the liquid must be set at 1/(4-3%).

In addition, if the combination reaction of formula (3) Ic is carried out under appropriate conditions taking into consideration the conditions listed above, 4. Invention compound (+)
The method for preparing the compound (1) of the present invention can be carried out in C with very good yield.
1 indicates. stomach! It is limited only to if, , and 71 et al., and there is no Ql.

Examples] 1-Menal;)-Self-formation of hydroxypyrazole
(Fl. 57).

After cooling to 0° C., 25 W (0.5 mol) of methylhydrazine was added to the reaction mixture while maintaining the reaction crystallinity below fO°C. tl. ! After stirring for 1 hour, 3 U mg of hydrochloric acid was added to the reaction mixture and the mixture was refluxed for 2 hours. When the reaction was completed, the M flow cooler stand and water outside of reactor a were replaced with device i, and the reaction mixture e (butanol was added thereto, followed by azeotropic dehydration).

After completion of dehydration, nopatanol was distilled off under pressure, and the remaining 11 was converted into crystals (7. Rokuki Target Compound 68"/(f) Shizuka 687 ru) Shiden [night temperature and (7tetoku/ζ. 11 prongs 4s y 6 9o
, l;'r1 point 1 5 5 ~ 1 4 7
℃.

Real b1! Ruth24-(2,4-dichlorobenzoyl)~
1-Me r Ru 5-hi 1' +6 formation of Roxibifusol (![→.

1-Methyl-5-1 nidrogisibiran°-9,81 (
01 mole)? r, monolium hydroxide 40v (1'1.
1 mol) of thorium that turns into water? IM30
mg by ra at room temperature and fc. 1 (] t) of this water td liquid
''(While maintaining Ic, 2.4-dichlorobenzylchloride 23. Doshi, Sonogi 2 [
The mixture was stirred for 2 hours at 1 Y', jJ, l.

Chloroporum, layer 3, from the reaction mixture, water.

Sequentially with 5% sodium bicarbonate aqueous fik, No. 11 saline solution, dry, and evaporate in a bathtub (2 steps).

1-1f-5-(2.4-zochlorpensoyl-oquine)-pyrazole 2 5. 5 jJ was obtained.

(Yield a b 9 g) This 1-methyl-5-(2,4-dichlorobenzoyl'xy)-pyrazole 2 Fl. 3 v (+
1. [] 7 5 Gil) and Su1 (!, Ice Charcoal (9 Potassium 2 [1.8 W (01” Gil) (r:
J'L <jjLself' 1. , (2i, Vc
) JI11hA.

Hard 14, Gako j #IJ1. l , , l+'J 1
'i II 1゛17 After solidifying (with ), further p
r, 1 3.11 ~ 1 5 II' [J(:
2 hours] 111 fever 1, ri.

1zo response γ [i. Table + I17I order - After releasing i, add Inglovir alcohol 5 [11 tiger, NΣ11, ((1
Time bending reflux (,ta.

After exhilaration, /k 1 II O mεtongue 11,
” Hydronic acid r-wave property, ri u o ; l ; j rem 2 0
[1 ml 4 ml ",") <+;
i1'l' L-i.

The solid was crystallized with 95% J ethanol +: r p + -0, and the 4-(2,4-dichlorobenzoyl)-1
14.4 ri of -nonal-5-hydroxypyrazole were obtained. (Yield 71%) Melting point +81. [1-181. st” (colorless old crystal) old, l+= (δ, ppm, (!])C4)
: 5.68 (3++, s), 7.58~
7.61 (40), 8.01 (IEl, s)'
J-b1MIl! lF5 Synthesis of 4-(2,4-dichlorobenzoyl)-1-methyl-5-(2-pyridylmethoxy)pyrazole (compound number 4) 4-(2,4-
dichlorobenzoyl)-1-methyl-5-hydroxypyrazole 1°56/(0005 mol)? 1. l Trienalami71. Ll I W (0.01 mol) Benzene 20. Releko bathing/? 1-o3-Σ et al., 2-picolyl chloride salt 1 pig 1 no B 2 y
(Il, +105 mol) and heat for 5 hours.
Ic 1. After the mixture was completely cooled, 7 tJ of 4 was produced and distilled off by reducing the pressure of the bath medium. N1
Runonoramuku stomatography (benzene in td output 6:
Ethyl acetate-4:1)11C-(nJpItIL,
LJ p41 1.42 W 147e, llK rate 7 a 516° Melting point 5(] ~ 55°C NbIR(δ+ rl 11111, (: l'
lfs): 5.65 (3H, s), 5.6[]
(2N, s), 7.30~7.72 (7E mouth,
8.57 ([1, (1) Implementation?! 14- 4- (2
,4-dichlorobenzoyl)-1-menalu-5-(2-
Nanonaruogishi) Bifun-) Shibi) Synthesis (・chemical)1
No. 6) 4- (2,4-dichlorobenzo・rr)
-1-methyl-5-hydroxyvirazole 1.56r(
0005 mol), ]・riage ethylmine [1,s 1y
([1,n [157/L-1, benzene 2 If l
to the /IA compound of 1le.

2-Prommenalnanomelene 1. + 1 y (o,
Add 5 mol of oυ and boil for 2 hours. After cooling.

Pass the salt through 3θ4, remove the preservative medium and leave it in.
[rat] kγ111-like gyu I no ni monoga r n --\
Purpose with seven Dan-benzene Jtt ++1 crystal l-! 1)
Obtained 1627 J.

Yield 64 Talo +1 IO Melting point 89 to 92 left old,! 1 cost δ, t) pm, fTIM! /, ):
5. bO(51+, s), 5.68(2H,
s), 7.21-7.9 II (11111th order V
C1 Actual method 113 and 4 according to the method 11
(Ij'<zu compound-1m was synthesized.
and 4. (1) The compounds of the present invention are also shown in Table 1.

formula.

Fall.

- (: Compounds to be coated No. 1 Table 1 - (:: [Coat at 11°) Compounds to be coated No. 2 Coating Compounds of the present invention are used as herbicides (l per w-it, generally) 3j1 Uniform solid phase (for example, clay, melk, bentonite, diatomaceous earth, etc.)4,
Fi-water, alcohol, etc.), aromatic hydrocarbons, ether carbon, gas, etc.)
Jl, Korsupuru Ji (river-l crest enal 卆 Th 1. LV ad ξ d kō (jimenal holm abad temple) nato's shin body carrier 1+ and l kun) + 1 1. F9 "3: emulsifier, n) i cut. yh++v Shu agent, penetration ha (
1. Apply laxatives, stabilize wounds, etc. on both sides. It is possible to administer IJti to Tenkawa in various dosage forms such as cutting, irrigation, first dose, and granules.

- Also if necessary - C-made spear &. l'tiYi11
Other yuzu herbicides, yuzu insecticidal hari, yu-hari, and synergist nato-a may also be used in combination.

Next, all the formulation examples of the elasticity in the case where the compound of the present invention is present will be shown. rfli &. Name the part. However, the formulation example r. l' is not limited to these horns.

Blend 11 grains 1 (1j or more) Uniform vC (IC, powder (i% L), add a small amount of water, (+7 41' mix, press No. 11, extrusion type ladle) Granulate and dry.

Formulation example 2 Water I II roll Contain the above - evenly mix W>j (+'? and add water A11 agent. 1 History 711 VC removed) 1 to I LI U When multiplied by 0, the culling component h1 is 0. per hectare (+ta) [ ] 25
Ferment it until it becomes 4f per 10kg. Note 1
The compound of the present invention is suitable for use in agricultural fields such as fields, water fields, rice gardens, etc., as well as vacant lots and roadsides.
Jl place ((Okeru Taniyu Mu 4)'t, /j taste V como i4 Jul-to do -C, its biIi river bridge t &-, i kome Kawaba kyo bi;i period, Is there a difference r1 depending on the application method, target grass 4! The proportion of

Next, as a defibration agent for the compound of the present invention, the following tests were carried out in the city of C. The dimensional VC is revealed in U.

i・iI,,J・V/1:1lIf'/J(M lees effect trial acclimation (1)'/111. OU 11"r-
After putting alluvial soil into the Neubauer Bonol shell, water was mixed with C to create a diving condition of 2 Qn water depth. Evening/f
Nujiko, Konagi, Azena, Gikashigusa, Hotarui's 1st yuzu, -d] 4 bot and mixed oil t=, history V
Ni Urikawa lump sumi i Zuno j Yasori lump sumi, ri IJ guri f lump (i (stand 1θ floorboard).

The next day, (-σ) water tf+i herv1>t (/>-3
``iVC,'' UVC, and the preparation were treated with Mesubivent.

Three weeks after the application of Rakuju, the herbicidal effect of x' 4 was confirmed, and the publication standard of the lower version was also adjusted.

The results are shown in Figure 5.

Publication-Bi Standard 5...Almost 0% or more (IJ almost completely withered)4...〃7 (1-911%6...
・ 17411~7 II N2... 〃 2[
j ~ 40 evening J 1... 〃 5 to 2 fl me to 0... 〃 59J and above] - (Hato place) jth 4
The ground 1411 grass wagon and jail, the ground ii and li grass wagons of treatment 14 were all measured and watered according to the formula 1.

Table 3: Structural formula of compound B in Table 8:
Thick and thin tyur was synthesized according to the formula 41 of 1 (compound with relative softness ratio of 11) and compound l) with 16 formulas: (A compound with a soft ratio of 1C and synthesized according to 11 VC) As is clear from Table 3, 1 The compound of the present invention has strong herbicidal activity against annual weeds as well as perennial weeds, whereas the herbicidal efficacy of the control compound rapidly decreases as the system layer decreases. are doing.

fA experiment example 2 herbicidal effect test under flooded conditions (2) 4,
. . Alluvial soil was placed in a 0 are Fuguol pot, and then water was added and mixed to create a water-filled condition with a water depth of 2 crn.

A lump of Japanese cypress collected from a perennial offshore Tako paddy field in the previous year, a lump of logwai, fi? R. Firefly seeds were sown in the soil of the Wagner pot under the above-mentioned flooded-F conditions. Immediately after the weeds germinated, the diluted chemical solution was poured onto the water surface using a graduated pipette so that the chemical concentration was constant.

Leaf Droplet 1. After a week, the total live weight of various miscellaneous items 1 was measured.
The weed killing rate (weed) was calculated as fc0.However, the whitened parts of weeds are considered as dead parts, and the results are shown in Table 4.

Table 4 Compound A Compound A Compound [C and Compound 1]
This is the same control compound as IIj Keisuke Mukai.

As is clear from Table 4, the 9 compounds of the present invention are Mizuguchi-y+
Ik 1s)j Weed control agents such as firefly, water cyperus, and cypress are able to overcome their weeding power even with a low amount of VC, but with the control agent, VC, which results in a lower amount of cypress.
Therefore, in Volume 5, the killing power is noticeably low.

Test Drive Reli 3 Water Juice V
Alluvial soil was filled in the Neubauerbono area of 1 o, o o uar, and water was poured into the area.
Cm tlb 71< condition and (7).

H: Sadano Kuwa td's Shiba agent retouching review: Subordinate 1 to the surface of the water.-C bale.

Soil surface layer 2 D11 was thoroughly mixed and stirred. After 21.1,
Grown in a *ω° box in advance-I! 41 at the 25 leaf stage
1 (variety: Nihon Naikai), the growth status of the upper S. neupawel bosoto p (2 plants each, 5 knr transfer 4111IL, . . . 1 lyc 11) was investigated for 1 month. tl, zo) 1 treatment rate is 5 kv per hectare,
The test was conducted in a 2.5 kg test plot.

7'1. The results of the Gs trial and Rico area are unprocessed 14
Compared to.

The growth conditions are almost the same for fertile and 11 < 43, and no chlorosis (whitening) was observed in contrast to persimmons (7).
I made sure that Saigo wasn't there.

5th Clothes V Here are the results.

Section B Sixth Criterion: 5...Crops are almost completely withered 4... 〃 Significant phytotoxicity 6, 〃 〃 No phytotoxicity observed 2... 〃
〃 Some drug damage is observed 1... 〃
Almost no drug damage is observed 0... l
One compound with no chemical toxicity Ci was the same control compound as in Test Example 1.

As is clear from Table 5, the compound of the present invention has no phytotoxic effects on paddy rice even at commercial doses, but the comparative compound (■)
The manifestation of drug damage is remarkable.

Time W [Applicant: Nissan Chemical Industries, Ltd. 7, Tsuboi-cho, Funabashi City
22-1 Inside the Central Research Laboratory of Nissan Chemical Industries, Ltd. 0 Inventor Norio Tanaka 722-1 Tsuboi-cho, Funabashi-shi Inside the Central Research Laboratory of Nissan Chemical Industries, Ltd. (C Inventor Masashi Matsunaga 3-7 Kanda Nishiki-cho, Chiyoda-ku, Tokyo) 1 Within Nissan Chemical Industries, Ltd. Inventor Takashi Inokai 1470 Oaza Shiraoka, Shiraoka-machi, Minamisaitama-gun, Saitama Prefecture Inventor: Kin Nanamaki 1470 Oaza Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Prefecture Nissan Chemical Industries, Ltd. Nissan Chemical Industries, Ltd. Biochemistry Research Institute

Claims (1)

[Claims] In the formula, A (1 lower alkylene group =, +, ,
Z i + naophene, penzonaonoene, pyridine 2 quinoline, -(sooxazole, benzoxazole, uracil, pyrimidine, 1,5.4-thiadiazirone, 1.5.5-triazine, oxazole, 1,2.3
-benzotriazin-4-one, benzoxacilone,
Benzimidazole, benzofuran, hirazine, 0--
Piron. Kuhnlin, In1'-le, Hi'roll, Fran-maf
r,,Q-[choose from naphthalene]1- fC”1
7 units are removed.Je1゜However17. Konoshira aroma r, t, i
tk class alkyl group. Lower alkoxy group, rogen base, nitro group. 1 to 61 selected from Aζ group, phenyl group, futenogishi group' or rtl/linololomethyl group
The rr substituent may be used to convert the shofukurokzu 1u character. ) expressed as 1
1 pyrazole visits patients. ('11゜''(: Iwasa f+ru chemical specialty and quadratic formula (Ill) 'lh
J, / -A -z (Ill) (where ΔCr represents a lower arylene group 1.Z&-1 naonoene, benzothiophene, pyridine. quinoline, inoxazole, penzogisazole, uracil, pyrimidine, 1,6 .4-gamma diazirone, 1
, 6.5-1-tridin, oquinazole, 1,2.5-benzotridin-4-one, penzoogizazolone, benzimidazole, benzofuran, pyrazi/, σ-pyrin. Coumarin, -(ndole, virol, noran'matc
+-t)-Selected from the Monkey of Tsutareno 71-Shows Hosai-ho 4゜lI 17. This JL, aromatic ring Q, lower Al 4
・Le group. II-! ; 7 groups, halogen atoms, 21 days pattern. Amino group, phenyl group, phenyl group - The general formula (1) that can be fully reacted with the compound in which it is spread and its features: .) How to make one Pyrazole Furikichi. (3) General formula (■): (H4゜(In the formula, ΔeL1 represents a hollow algylene group, 2 is naophene, pensina A phen, pyridine. Quinoline, isoxazole, penzokylyzole, uracil, pyrimidine, 1, 5.4-nadiazolone, 1,6.5-) riazine, ogirisol, 1,2.
3-bencitriazine/-4-lambda, penzokylysolone, benzimidazole, penzonorane, hirazine, σ-pyrone. Indicates a lotus aromatic ring from coumarin, in-1-nod, virol, furan or naphthalene. However, these characteristics 1-狽i, 1. , 11 (Vl, argyl group. lower r-rukogyshi group, hagen DX child, 2l-0&. aba) group, phenyl group, fenogyshi X - * f? :,
may be fm-substituted with 1 to 6 substituents selected from trifluoromethyl groups. ) 14 special visits to the talented Bifsoru! II-More than 121 insects
A selective herbicide characterized by containing it as an active ingredient.