JPS6118755A - Arylsulfonyl fatty acid amide derivative, its preparation, and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [R is H, lower alkyl, or Cl; m is 1, or 2; R<1> is lower alkyl, or lower alkenyl; R<2> is lower alkyl, lower alkenyl, group shown by the formula II (X is lower alkyl, halogen, etc.; n is 0- 3), etc; R<3> is H, or low alkyl; R<2> and R<3> form 4-6C saturated ring]. EXAMPLE:N-(2,4-Dimethylphenyl)-2-(2-methylphenylsulfonyl) propionic amide. USE:A herbicide. Showing improved action on annular weeds in paddy field, such as Echinochloa crus-galli Beauv. var. praticola Ohwi., umbrella plant, etc. and perennial weeds such as water nutgrass, arrow head, etc. PREPARATION:An arylsulfonyl fatty acid derivative shown by the formula III or its reactive derivative is reacted with an amine derivative shown by the formula IV optionally in the presence of a reaction auxiliary such as thionyl chloride, etc. in a solvent such as acetone, etc. at room temperature or under cooling or under heating for 1-5hr, to give a compound shown by the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (1) Object of the Invention Industrial Application Field The present invention relates to a novel arylsulfonyl fatty acid amide derivative, a method for producing the same, and a herbicide containing the derivative as an active ingredient. Therefore, it can be effectively used in the fields of organic chemical industry and agriculture and horticulture.

BACKGROUND OF THE INVENTION The following compounds are known as compounds similar to the arylsulfonyl fatty acid amide derivative of the present invention.

■ [Chem, Abstr, J Volume 72 71Z79
Page 026f and Japanese Patent Publication No. 46-7104
2. Bara oo phenoxy and n = 1~
It is 3.

These compounds are used as raw materials for isothiazoline derivatives that exhibit fungicidal properties, but their herbicidal activity has not been described.

■ [Chem, Abstr, J m Volume 88, No. 1
Page 20723 b It has been reported that there is a bactericidal effect (gθrmicidal), but there is no mention of a herbicidal effect.

■ [Ch, em, AbBtr, J Volume 92, No. 6
Page 76q7a It is described as an intermediate for producing raw materials for Kafuu Photographs, and its herbicidal activity is not described.

■ [chem, Abstr, J *: x s 6
Volume 159,577m It is described as a raw material for rice bran to obtain an addition reaction product by reacting with nitrostyrene, but there is no mention of its herbicidal action.

■ “CMm, Abstr, J Volume 32, No. 164
Page 380 In the formula, X is 4-C4, 4-OCH3,4-No
2 indicates 4-CH5. Although it is described as a raw material for reacting with each diazonium salt, there is no mention of its herbicidal activity.

■ [Chem, Abstr, J Volume 41, No. 39
Pages 02t-3913C It is described that it exhibits a plant growth regulating effect.

■ l Chem, AbStr, j Vol. 68 No. 34
53631-page X1jH, CH3, 'C1IIBr in the formula
, No2 (0-1m-1p-) or OCH3.

Although NMR data for hydrogen atoms on the ring are described, there is no description of herbicidal activity.

■ [Chem, Abstr, J Vol. 71 No. 1o1
On page 493j, there is a description that it exhibits herbicidal activity and plant growth regulating activity.

Problems to be Solved by the Invention Conventional arylsulfonyl fatty acid amide derivatives (the above C
, A) have almost no activity as herbicides. The present invention provides novel arylsulfonyl fatty acid amide derivatives that are highly practical as herbicides in place of these conventional derivatives, a method for producing the same, and a herbicide.

(2) Construction of the Invention The present inventors have synthesized a large number of novel arylsulfonyl fatty acid amide derivatives and have conducted extensive research on them.

As a result, it was discovered that a series of compounds represented by general formula (I) are useful as herbicides.

In the formula, R represents a hydrogen atom, a lower alkyl group or a chlorine atom, and 1m represents an integer of 1 or 2.

R1 represents a lower alkyl group or a lower alkenyl group
R2 represents a lower alkyl group, a lower alkenyl group, a rogen atom, a lower alkoxy group, or a trifluoromethyl group, and n is 0.1.2 or (in the hole, p is an integer of 0.1 or 2). ) group, α-methylbenzyl group, α, α
-dimethyl be/zyl group or tetralinyl group, and t represents a hydrogen atom or a lower alkyl group, or R2 and R3 form a saturated ring having 4 to 6 carbon atoms.

Action The compound of the general formula U+ does not cause any phytotoxicity to paddy rice, and is effective against annual weeds in paddy fields such as Japanese field weed, Japanese cypress, Japanese cypress, and Kikashigusa, as well as on perennial weeds that have become a problem in recent years, such as Japanese cypress, Japanese cypress, Japanese cypress, and Japanese black grass. It shows strong herbicidal action against. Also, crabgrass,
Chickweed.

It is also effective against vertical grass, dogfish, 21-year-old snails, purslane, black-and-white grass, whitewort, Japanese sedge, bindweed, Japanese cypress, Japanese cypress, sycamore, sycamore, shepherd's purse, foxtail, etc. Therefore, it is not only particularly effective as a herbicide for paddy rice, but also useful as a herbicide for field crops and other cultivated and non-crop lands, and these effects can be expressed by soil treatment or foliage treatment. Furthermore, the compound of general formula (I) is not toxic to humans, livestock or fish and shellfish, and can be safely used without any foul odor.

Next, the method for producing the compound of general formula (I) of the present invention will be specifically illustrated by the reaction method of Reaction Scheme 1 and Examples. In the formula, R, m, R', R2, and R3 have the same meanings as above.

[Reaction formula] % formula % () To produce the compound of the present invention, the amine derivative represented by the general formula (2) is mixed with a suitable reaction solvent such as benzene,
It is dissolved in toluene, xylene, chlorobanzene, dioxane, tetrahydrofuran, methylene chloride, acetone, methyl alcohol, and the arylsulfonyl fatty acid represented by the general formula (TI) or its reactive derivative is added directly or Dissolve in the above organic solvent and add. Then, the reaction is carried out at room temperature or while cooling or heating as necessary. The reaction time is 1 to 5 hours. Reactive derivatives of arylsulfonyl fatty acids include acid anhydrides, acid chlorides, acid bromides, and carboxylic acid esters, which can be easily obtained from arylsulfonyl fatty acids by applying known methods.

Further, when reacting the amine derivative of general formula (2) with the arylsulfonyl fatty acid of general formula (rr) or its reactive derivative, a suitable reaction aid such as thionyl chloride, phosphorus trichloride, or phosphorus pentachloride is used.

Phosphorus oxychloride, dicyclohexylcarbodiimide, triethylamine, pyridine, N-methylmorpholine, N
, N-diethylaniline, sodium hydroxide, sodium methylate, sodium carbonate, potassium carbonate, etc. can all be used. These reaction aids are preferably selected and used depending on the type of arylsulfonyl fatty acid or its reactive derivative.

After the reaction, the reaction aid is removed by filtering or washing the anti-16 product with water, and the organic solvent used is distilled off to obtain the arylsulfonyl fatty acid amide derivative represented by general formula (I) with high purity. Moreover, it can be obtained in high yield. These compounds further include acetone, methyl alcohol, benzene, toluene, chloroform
% It can be further purified by crystallization.

Next, Examples will be described; however, the present invention is not limited to the methods disclosed in these Examples.

Example 1 2-phenylsulfonyl-propio/acid 2.147(1
Thionyl chloride 54 (42 mmol) was added to the flask, and refluxed for 1 hour using a reflux condenser equipped with a calcium chloride tube. After that, excess thionyl chloride is distilled off under reduced pressure, resulting in 2
-Phenylsulfonyl-furopionic acid chloride was obtained as a yellow oil.

Separately, 1.78 S' (10 mmol) of 5-chloro-0-toluyrine and 20 mmol of acetone were placed in a 50-capacity eggplant-shaped flask, and while stirring in an ice-water bath, 2.12 S' (20,8 mmol) of triethylamine was added. mmol) was added. 2-Phenylsulfonyl-propionite tarolide dissolved in 5me acetone was then added dropwise over 10 minutes at 5-10 DEG C. and the mixture was heated to reflux for 60 minutes.

After recovering 15 mL of acetone, the reaction mixture was returned to room temperature and poured into 150 mL of water.

The folded crystals were washed twice with water and re-crystallized from ethyl acetate to give 2.92% of white crystals.

Melting point 125.5-126.5° C1 Yield 86.1%.

Example 2 2.4-dimethylaniline 1.21f (10 mmol)
and 1.0 f (10 mmol) of calcium carbonate into a four-headed low-bottomed flask, and then 20 ml of acetone. While keeping the internal temperature at 5-10°C in an ice water bath and stirring, add 2.47f (10 mmol) of 2-(2-methylphenylsulfonyl)propionic acid chloride to 5% of acetone.
MI! After dropping a solution dissolved in
Heat to reflux for 0 minutes. Then, 15% of the acetone was distilled off, the temperature was returned to room temperature, and the mixture was poured into 150% water. Extract 3 times with 50% ethyl acetate, wash in sequence with 5% hydrochloric acid aqueous solution, 5% sodium carbonate aqueous solution, and water, add 57% sodium sulfate, stir, dry, filter, and distill off the P solution of ethyl acetate. N-(2,4-dimethylphenyl)-2-(2-methylphenylsulfonyl)fropion fp27 mi)'
White crystals of 3.18 ? (Yield: 96 cm) was obtained.

Melting point 126-124'C0 Example 3 2.5-dichloroaniline 1.62r (10 mmol)
1.22 f (10 mmol) of dimethylaniline and dimethylaniline are placed in a Mr. Yokukumaru flask, and 20 mm of benzene is added to the flask. Keep the internal temperature at 10°C in an ice water bath and add 2-(6-methylphenylsulfonyl)furopionic acid amide vv2. without stirring. ayi (10 mmol) to benzene 5d
A solution dissolved in was added dropwise over 10 minutes, and then heated under reflux for 1 hour. After that, return to room temperature, add 301 parts of benzene and 5 parts of water.
0m/l! Add and stir, then transfer to a separating container.

Separate the layers to remove the aqueous layer, and remove the benzene layer from a 5-functional aqueous hydrochloric acid solution.
Wash with a 5% aqueous sodium carbonate solution and then with water, add 2f of calcium chloride, dry, and sieve. When the benzene in the P solution was distilled off, 3.5ss+' (yield: 95cm) of white crystals of 1'-(2,5-:)chlorophenyl)-2-(6-methylphenylsulfonyl)propionic acid amide were obtained.

can get. Melting point 92.5-95.5°C0 Example 4 2-Methyl-5-fluoroaniline 1.25? (10 mmol) and triethylamine 1.1F (10,9
Put 20 mA of benzene into a round neck flask and add 20 mA of benzene. The internal temperature was maintained at 5 to 10°C in an ice water bath, and while stirring, a solution of 2.60f (10 mmol) of 2-(4-methylphenylsulfonyl)butyric acid chloride dissolved in benzene 5- was added dropwise over 10 minutes. After, 3
Heat to reflux for 0 minutes. The reaction mixture was then returned to room temperature and added with water 3
Add 0ml/30ml of benzene, stir and transfer to a separating container. The aqueous layer separated by standing was removed, washed in this order with a 5-chloride aqueous solution, a 5% aqueous sodium carbonate solution, and water, and 22 ml of Glauber's salt was added, stirred, and dried.
1A. If benzene in p-liquid is distilled off, lq -(2-
White crystals of methyl-5-fluorophenyl)-2-(4-methylphenylsulfonyl)butyric acid amide 3.41 ?
(yield 97.7%) is obtained. Melting point 128-129
．． 5°C0 Example 5 2-. 7'Tyl-5-chloroaniline 1.42F(1
0 mmol) and 1.01 (10 mmol) of calcium carbonate are placed in a neck round bottom flask and then 25 mff1 of acetone is charged. Keep the internal temperature at 5-10°C in an ice-water bath, stir, and stir for 10 minutes to dissolve a solution of 2.75 f (10 mmol) of 2-(4-methylphenylsulfonyl>valerin wyy loride) in acetone 511I! After adding dropwise, the mixture was heated under reflux for 1 hour. 20 kg of acetone was distilled off and the temperature was returned to room temperature. 801 rLt of benzene and 50 l of water were added, stirred, and placed in a separating vessel to separate and remove the aqueous layer. The mixture is washed with 5 parts of a 5% salt aqueous solution and 5 parts of a sodium carbonate aqueous solution, and then with water, 2 parts of sodium sulfate is added thereto, shaken, dried, and filtered.

To distill off benzene from the furnace solution, N-(2-methyl-5-
Chlorophenyl)-2-(4-methylphenylsulfonyl) Koto G-taamide white crystals 3.7! M' (yield 99
h) is obtained. Melting point 155-156"C0 Example 6 1.285' (10 mmol) of 2-chloroaniline and 1.06r (10 mmol) of 2-chloroaniline are placed in a neck round bottom flask and 2 or 111 of acetone is added. Bring to internal temperature in an ice water bath. A solution of 2-(4-ethylphenylsulfenyl)propion dichloride (2.619C, 10 mmol) dissolved in acetone (5d) was added dropwise over 10 minutes while stirring, and the mixture was refluxed for 1 hour. do.

Toluene 501 after distilling off 10 punishments of acetone! Add Ll and 50 g of water, stir and transfer to a separating container, separate the liquid and remove the aqueous layer. Next, the mixture is washed with a light blue solution of 5-thihydrochloric acid, an aqueous solution of 5φ reconstituted sodium acid, and water in this order, and 22 ml of sodium sulfate is added thereto, shaken, dried, and filtered. If toluene in liquid F is distilled off under reduced pressure, N-(2-chlorophenyl)-2-(4-
White crystals of ethylphenylsulfonyl) fropionic acid amide 3.45 f! (yield: 98 cm).

The melting point was 89.5-90.5°C.

Sou 7J+ii Example 7 2.5-dichloroaniline 1.62r (10 mmol)
and dimethylaniline 1.225' (10 mmol)
into a round neck flask and then add 25 ml of toluene.
Add r and J. Keep the internal temperature at 5-10°C in an ice water bath.
After stirring, a solution of 2-(2,4-dimethylphenylsulfonyl)propionic acid chloride 2.615' (10 mmol) dissolved in toluene 5- was added dropwise over 10 minutes, and then stirred at 80°C for 300 minutes. Next, this was returned to room temperature, 2017Le of toluene and 50 - of water were added and stirred, and then transferred to a separating furnace and separated to remove the aqueous layer. Wash in this order with a 5φ hydrochloric acid aqueous solution, a 5-diaphragm sodium carbonate aqueous solution, and water [7. Add 22 grams of Glauber's salt, mix, dry, and filter. If toluene in the furnace liquid is distilled off under reduced pressure, N(2+5 9chlorophenyl)-2-(2,4-')
White crystals of y'f ruphenylsulfonyl) propionic acid amide 3,79 (+4 fold ratio 96 yen) are obtained. Melting point 137-139'C8 Example 8 2-trifluoromethylaniline 1.61? (10 mmol) and triethylamine 1.1r (10,9' mmol) were placed in a round-necked round-bottom flask and benzene 25
Add d. 2-(6-chloro-4-methylphenylsulfonyl) fropion macrolide 2.817 (10 mmol) was dissolved in Begdan 5-5 while keeping the internal temperature at 5-10°C in an ice-water bath and stirring. The solution was added dropwise over 10 minutes, and then heated under reflux for 30 minutes. Thereafter, the temperature was returned to room temperature, 30 d of benzene and 50 d of water were added, the mixture was stirred, and the 7X noso was removed. The benzene solution was washed with 5 parts hydrochloric acid aqueous solution, 5 parts sodium carbonate water bath, and 11114 parts of water, 21 parts of sodium chloride was added, mixed, dried, and filtered.

When the benzene in the P solution is distilled off, N-(2-toIJfluoromethylphenyl)-2-(3-chloro-4-methylphenylsulfonyl)furopionic acid amide 5.9? (yield: 96 cm). Melting point: 76.5-79.5°C0 Example 9 1.259 (10 mmol) of 2-methyl-5-fluoroaniline and 1.01 (10 mmol) of calcium carbonate were placed in a four-necked, nine-necked flask, and 20 minutes of acetone was added. Add. The internal temperature was maintained at 5 to 10°C in an ice water bath, and while stirring, a solution of 2-(4-chlorophenylsulfonyl)propionic acid chloride 2.67F (10 mmol) dissolved in 5 hours of acetone was added dropwise over 10 minutes. Afterwards, the mixture was heated at high speed for 1 hour. Acetone 151 is distilled off and the temperature is returned to room temperature. Add 50 ml of water and 50 ml of ethyl acetate, stir and transfer to a separating container, remove the aqueous layer, and add 50 ml of ethyl acetate.
The mixture is washed with an aqueous solution of dihydrochloric acid, an aqueous solution of dihydrocarbonate, and water in this order, and 37 g of sodium sulfate is added thereto, mixed, dried, and filtered. When ethyl acetate in P solution is distilled off, N-(2-methyl-
White crystals of 5-fluorophenyl)-2-(4-chlorophenylsulfonyl)furopionic acid amide s, 4 s
y (yield: 97 h) is obtained. Melting point 118.5-1
20.5°C0 Example 10 1.41 f (10 mmol) of 2-methyl-5-chloroaniline and 1.5 g' (109 mmol) of potassium carbonate are placed in a round bottom flask and 30 g of benzene is added. Keep the internal temperature at 5 to 10°C in an ice water bath, and add 10% of a solution of 3.01 f (10 mmol) of 2-(2,5-dichlorophenylsulfonyl) furoyl chloride dissolved in 5 d of benzene while stirring. Add dropwise over a minute and heat to reflux for 1 hour. Return this to room temperature, add 20 ml of benzene and 50 ml of water, and stir.
Transfer to a funnel and separate to remove the aqueous layer. The benzene layer was mixed with a 5φ salt-intoxicating aqueous solution, a 5% sodium carbonate aqueous solution, and +t of water.
After washing it thoroughly, add 3 ml of Glauber's salt, shake to dry, and pour over. When the benzene in the r liquid is distilled off, N-(2
-Methyl-5-chlorophenyl) -2-(2,5-dichlorophenylsulfonyl)-2-(2,5-dichlorophenylsulfonyl) white crystals of phlopionic amide (3.95') (yield: 96 yen) are obtained.

Melting point 120-122°C0 Compounds produced by the method of the invention are listed in Table 1.

First element analysis value (upper row: calculated value, lower row: actual measured value)
0% H% C1% Nl 0%
8% F%49.05 3.34
9,05 3.58 12.25 8.1
8 14.55 & 9.06 3.33 9.
[183,5612,218,2014,5/)64.
33 6,034. ．． 41 15.12 10.
1064.30 6.06 4.3
9 j5.14 10.1165.23 6,
39 4.23 14.48
9.6765.24 6,40 4
．． 20 14.48 9.68+S5.23 6
．． 39 4.2314.48 9.
6765.25 6,36 4.2
2 14.49 9.6B56.88 4.7
7 10.50 4.15 14.21
9.4956, B6 4.79 10.51
4.17 14.22 9.4556.8B
4.77 10.50 4.15 14.
21 9.4956.89 4.75 10
．． 52 4.13 14.23 9.48a
H% ct person Nchi O person S
Section F compound 0% H% cL% N4 0chi 8% F%6j, 28 5,72
4.18 19.20 9.
6256, B9 4.79 10.48 4.1
3 14.23 9.4856, B5 4.7
8 10.54 4.14 14.19 9
．． 50 compounds 0% H% ct% N% oqb
s% 7%) D, :35 Q, Y U
So, 66 5.83 17.
42 8.69 Compound H% ct N-O S S F 4.34 3.77
12.92 8.63 15. ! 154.35
．． 3.74 12.94
8.65 15.335.65
4.62 15.82 10.575.68
4.60 15.80 1 [
1,594,7710,504,1514,219,4
94,7810,524,1314,239,484,
7710, 504, 1514, 219, 494, 781
0,514,1614,199,474,7710,5
04,1514,219,494,7910,504,
1314,259,484,0619,055,761
2,898,614,0319,073,7412,8
98,63 ct H5, ct% N% o% 8%
1i%/1.03 19.04 3.78
12.87 863.1. n4 19.03
3.77 12.90 8.613.44
26.163.42 11.84 7.8
6C9, H Hagi CT Section N Chi O Section
S No F 64.33 6,03
4.41 1512 1n, 1064.3
1 6,06 4.40 15.
11 10.1265.23 6.39
4.23 14.48 9.676525
6.3B 4.22 14.47
9-6865.21 639
4.76 14.48 9.6665.23
6,39 4.23 14.4
8 9.6765.26 6,37
4.22 14.4.9 9.66 Compound 6% H La cL Shi N Section O Section
S Section F Section - 11 --- Rip -----------
−−■−! -Ichiichi Shizuku□, Ko, -ichi□
■■閤---Ki---■■-65.22
6,37 4.2614.48
9.6758.05,”), 16 10.
08 Ro98 1 Ro, 6A 9.115
R,065,141o,o73.97 D66
9.1058.113 51A 10,08
3.98 1364 9.1158, n5
5.14 10.04 3.97 13
．． 699.1158.0. ! i5.1610.0
8 3.98 13.64 9.115B
,00 519 10.07 5.9B
13. /+3 9.13/+0.88 5,4
1 4.18 14ro 1 9.
565.6660, B6 5.44
4.1'7 14,30 9.55 5
68Oe) +3 C'I H ct4 N 4 0
qA S l+ F +54.98
4,34 3.77 12.
92 863 15.3554.96 4,3
7 3.75 12.94
F3.66 15.3250.31 3.7. '
, 8,74 3.7I5 11.83
7.9n 14.0550,,”13 3.
75 B, 70 3.43 11.83
7.93 14. n358, n3 5.16
10.08 3.98 13. /, 4 9.
1158-qro 5.14 1o, [163,99
13659,1066,066,71Δ,05 1
3.89 9.2866.05 6.73
4.04 13.87 9.
31 compounds 58.0 58.0 52.8 52.8 61.8 56.0 56.0 et al H% ct% N section Ochi S section ・F 13 5.16 1
0.08 3.98 13.64 9.1
116 5.14 10.07 3.99
13.64 9.103 5.1610.0
8 3.98 13. lS4 9.110
5.18 10.06 3.99 13
．． 62 9.156 444 18.36
363 12.43 8.308 4.
41 18.38 3-67 12.39
8.327 5.77 4.0
1 13.74 9,18 5.446
5.77 4.03 13.73
9,16 5.459 4.71
3.63 12.45 8.32
14.796 4.74 3.64
12.45 8.33 14.78 Compound 0% H% ct% N% o%
8% F4 compound IJ', -L Cφ H duff ct% N% 0%
S Section F Section 6n, 07 5.82 9
,36 3.68 12.65 8.426U
, 4[1b, 50 9.41 3.72
12.70 8.470% H C
7chi N person Ochi S person F person 57.42 4. ! 57 3.52
12.08 8.07 14.3457.
45 4. ! 54 3.50
12.09 8.10 14.3267.89
6.78 377 12.97
8.6367.8B 6. '/9
3.74 1294 86558, n
3 5.16 10.08 Bird 98 1
3,64 9.1158.05 5,13
TO, 093, 9713619, 135F1.03
5.16 1f1.08 3.98 13.64
9.1158.02 to 18 10.0
7 3. '/9 13,64 9.105
2.86 4.44 18.36 3. /13
12.43 8.3052.88 4.
41 18.37 3゜65 12.40
8.2952.8/) 4.44 18
．． 363.63 12.43 8.3052.
83 4.4.7 18,34 3.63 1
2.418.52C% H% ct N
Section 0% S ＼ F Section 59.09
5.51 9,70 3.83 13.12
8.7659.0B 5.54 96
8 3.81 13.14'8.75'i
6. ['l19 4.71 3.6
3 12.45 8.32 14.79s
6. o6 4.75 3.61
12.46 8.34 14.7851.49
4. [+8 8.44 '3.34 N,
43 7.64 13.5851.46 4.
09 B, 46 3.35 11.43
7.65 13.5665.2 Otsu 6.5
9 4.23 14.48 9.
6765.26 6,37 4.2
2 14.47 9.68 Compound C%, J (1% C1% N%
o% sqA F%)2. U/
b, b4 so, 6 so 6.82
15.10 8.78 Compound Compound H4C7% N% 0% 8%
F7%5.51 9,70 3.83
13. j2 8.765.53 9
,71 3.82 13.12 8.744
．． 78 17.71 3.50 11.9
9 8.014.75 17.73 W
, dB 12. no 8.004.71
'l 17.71 3.50 11.9
9 8.014.78 17.70 3.
52 11.99 R,007,013,9
013,358,92 7,043,113,378,91 5,849,333,6912638,445,829
, 353A8 12. /17 8.436.1
0 3.85 13.21
8.8> 5.236.08
3.88 15.22 8,81
5. 24H staff CA staff T dirt” 0 壬
S Section F Section 5.04 3.
50 11.99 8. []4 14.284
．． 40 8,163.24 11. n9
7.3R13154,438,183,2211,1
07,3713,155,1810,063,9913
,639,135,1610,083,9813,64
9,115,1410,073,9815,659,1
0 Compound C 8% C4% N'lA o
5qAFIIZ compound C%, ) (% Ct'ly N% 0
1 8% F%58.05 5.15
10.07 3.99 1362 9.1
75 so, 05 5.56 9,72
3.85 13.11 8.74
C, H, ct, N9S, O, S, F, 61. B6! 5.78
4,03 13.72 9.
17 5.4451.62 4.06 19.
05 3.76 12.89 B, lN5
1, /, 5 4.03 19.08 3.74
12.90 8.6051.62 4.06
' 19,05 3.76 12.89
8゜6151.1 /1.08 19. n4
3.71 12.90 8.6R47,25
N47 26.15 3.4a 11,8
0 7.8847.28, S, 46:
26.18 3.40 11.81 7.8
759.09! i, 51 9.70 3
．． 83 13.12 8.7659.07
! ,'i,53 9.71 3.85 13
．． 11 8.73C% H% ct section
N Sorry Ochi Schi FLl)5
0.33 3,74 8.7'> 3.42
N, 83 7.97 14.0450.2
7,”,,6519.82 3.93 1
3.39 8.9450,? 9 3.67
19.97 3.94 13.20 E!
,9345,B6 3.10 27.06 3
．． 59 12.20 8.1958.03
5.16 10.08 3.98 13.
64 9.1158.05 5.18 10
．． 04 3.97 13.639.131jitdejukuctu ezCqA
H% C14N1 04, S section
'F%51, /)0 4. C1819,023
,7512,928,6342,142,6333,2
23,271+, 22 7.52 compound cty, H% Ct% N%
O'% 8%, y%-47
,283,4526,183,4111,Etrl
7.880% H ct Chi N9'
, M Sv F 65.23
6.59 4.2ro 14.48
9.6765.26. 6.5B
4.20 14.50 9.6659.76
6.814.9B 17.06 11.40
59.78 6,80 4.95
17.0611.41C% H4-ct%
NLI) 04 s*
F Chiro 0.99 7,17 4.7
4 16.25 10.8560.97 7.1
8. 4.76 16.26 1
0.8362.11 7.49 4
．． 53 15.51 10ro 6/12.15
7,47 4.50 15.51
105752.86 4.44 18.3
1S 3.63 12.43 83652
．． 87 4.42 18.35 Ro, 64
12.40 Fl, 3267.20 6,4
9 3.92 13.43 8.
9767.23 6.47 3.9
3 13.39 8.98 Unless the compound of the present invention is actually used as a herbicide, the compound of the present invention may be applied directly to the soil or foliage of crop cultivation areas in sweet form. However, in order to fully exhibit the herbicidal action of the compound of this defense, it must be mixed with suitable carriers and adjuvants, such as surfactants, binders, stabilizers, etc., and prepared into water concentrators, emulsions, and aqueous solutions using conventional methods. It is preferable to use it in the form of a preparation such as a powder, an oil suspension, a powder, a fine granule, or a coarse powder.

In the above, the carrier is not limited to a specific carrier, and may be any solid or liquid carrier as long as it is commonly used for pharmaceuticals. For example, solid carriers include mineral powders (kaolin, bentonite, clay, montmorillonite, Merck, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, apatite, white carbon, limescale, silica sand, ammonium sulfate, urea, etc.), vegetable powders, etc. (soybean flour, wheat flour, wood flour, grain flour, starch,
(crystalline cellulose, etc.), polymer compounds (petroleum resin, PoI
J iM chemically engineered nil ketone resin, dammar gum, etc.),
Examples include alumina, silicates, sugar polymers, monodispersible silicic acid, and waxes. As a liquid carrier, water, alcohols (methyl alcohol, ethyl alcohol, n
-f propyl alcohol, isoflobil alcohol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons 2M (benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrogen compounds (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, trichlorofluoromethane, dichlorodifluoromethane, etc.), ethers (ethyl ether, ethylene oxide,
dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl in butyl ketone, etc.), esters (ethyl acetate,
butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (:) methylformamide, dimethylacetamide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (:) methyl sulfoxide, etc.), alcohol Enitels (ethylene glycol monomethyl ether,
ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), industrial gasolin (petroleum ether, solvent naphtha, etc.), and petroleum lees (e-roughin, etc.) Examples include kerosene and war oil.

In addition, when preparing formulations such as emulsions, irrigation agents, and flowable agents,
Surfactants (still emulsifiers) are used for purposes such as emulsification, dispersion, solubilization, infiltration, foaming, lubrication, and spreading. Such surfactants include nonionic types (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, sorbitan alkyl esters, etc.), anionic types (alkylbenzene sulfonates, alkyl sulfosuccinates, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic type [alkylamines (laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.)], polyoxyethylene alkylamines], both a & 1 ．． C carvone powder (betaine type), sulfuric acid ester salt, etc.], but of course the present invention is not limited to these examples. In addition to these, various adjuvants such as polyvinyl alcohol, carboxymethylcellulose, gum arabic, polyvinyl acetate, gelatin, casein, sodium alginate, gum tragacanth, and the like can be used.

Furthermore, the compound of the present invention can be used selectively with other herbicides in order to improve herbicidal efficacy (2) or to expect a synergistic herbicidal effect. Examples of this include phenoxy thread herbicides (2,4-9 chlorophenoxyacetic acid, 2-methyl-4-chlorophenoxybutyric acid and their esters, thioesters and salts, 2-[4
-(5-trifluoromethyl-2-pyridyloxy)phenoxypropionate n-butyl]), liphenyl ether thread herbicide (2,4-dichlorophenyl-47-nitrophenyl ether, 2,4゜6- ) IJ chlorophenyl-4'-nitrophenyl ether, 2-chloro-4-) 'J fluoromethyl-6fuethoxy4
'-nitrophenyl ether, 2,4-dichlorophenyl-4'-nitro-37-medoxyphenyl ether,
2.4-') chlorophenyl-6-fumethoxycarbonyl-4'-nitrophenyl ether, etc.), triazine herbicides (2-chloro-4,6-bisethylamino-1
゜3.5-triazine, 2-chloro-4-ethylamino-6-inpropylamino-1,3,5-triazine, 2-methylthio-4,6-pisethylamino-1,3
．． 5-triazine, 2-methylthio-4,6-pisisopropylamino-1.3.5-)riazine, etc.), urea herbicides (3-(3,4-dichlorophenyl) 1
+ 197' f Luurea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea, 1- (
2,2-dimethylbenzyl) -3-p -)
3-chlorophenyl)carbamate, methyl-N-(
3,4-dichlorophenyl)-carbamate), thiol carbamate thread herbicide + 8-(4-chlorobenzyl)
N,N-diethylthiol carnocemate, S-ethyl-N,N-hexamethylenethiol carbamate), anilide thread herbicide (3,4-dichloropropionanilide, N-methoxymethyl-2,6-diethyl-α) -chloroacetanilide, 2-chloro-2',6'-diethyl-N-butoxymethyl)-acetanilide, 2-chloro-2,6-ethyl-N-(n-propoxyethyl)-
Acetanilide, N-chloroacetyl-N-(2,6-
ethyl phenyl) chrysin ethyl ester, uracil thread release agent (5-bromo-6-secondary butyl-6-methyluracil, 3-cyclohexyl-5,6-drimethyleneuracil, etc.), pyridinium chlorine herbicide (1, 1'
-dimethyl-4,4'-bispyridinium chloride, etc.), phosphorus herbicides (N-(phosphonomethyl)glycine, 0
-ethyl-〇-(2-nitro-5-methylphenyl-N
-Second-butyl phosphoramidothioate, 5-(2-
Methyl-1-piperidylcarbonylmethyl) -0,0
-di-n-propyldithiophosphate, 5-(2-methyl-1-piperidylcarbonylmethyl) 't”-
Diphenyldithiophosphate, ammonium-(3-
Amino-carboxyprobyl)-methylphosphinate, 2-amino-4-methylphosphinobutylalanylalanine, toluidine herbicide (α,α,α-trifluoro2.6-:)nitro-N.

N-dipropyl-p-nitruidine, etc.), others (5-
tertiary butyl-3-(2,4-dichloro=5-impropoxyphenyl) -1,3,4-, :, l-xadiazolin-2-one, 5-isopropyl-I H-2,1
,3-Benzothiadiazin-(4)-3H-one-2,
2-dioxide, α-(β-naphthoxy)-propionanilide, j-(2,4-dichlorobenzoyl)-1,
3-dimethylpyrazole-5-4-)luenesulfonate, 2C(4,6-:)methoxypyrimidine-2
-yl)aminecarbonylaminosulfonylmethyl]benzoic acid methyl ester), but are not limited to these.

In addition, the compound of the present invention may be used as an insecticide, nematocide, or
It can also be used in combination with fungicides, water-applied insecticides, soil-applied fungicidal insecticides, plant growth control agents, fertilizers, and the like.

The application value of the compound of the present invention represented by general formula (I) varies depending on the type of specific compound to be used, the type of cereals to be weeded, etc., but is generally 0.02 to 10 per 10 are. 2k
It is better to be in the g range.

Next, examples of the formulation of the herbicide of the present invention will be shown, but the proportions of active ingredients, carriers, and adjuvants, as well as their types, are not limited to the following examples. In addition, in the formulation examples, all parts are A1. Indicates the location.

Example 11 60 parts of hydrating compound No. 28, 281 of lignin sulfonic acid calcium salt! , 31flX of dodecylbenzenesulfonic acid sodium salt, and 65 parts of diatomaceous earth are thoroughly ground and mixed to obtain an irrigation agent.

Example 12 Granules 7 parts of compound Nn71, 2 parts of white carbon, 5 parts of lignin sulfonic acid calcium salt and 88 parts of clay
The mixture is thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, then granulated and dried to obtain granules.

Example 13 60 parts of granular clay, 35 parts of bentonite and 5 parts of lignin sulfonic acid calcium salt are ground and mixed, water is added, kneaded and then granulated and dried to produce granules containing no active ingredient. Granules are obtained by impregnating 95 parts of this granule with 5 parts of compound N[1106.

Example 14 Particles: 96 pieces of bentonite separated into particles of 300 to 850 microns
4 parts of Compound 1-83 were added to 1 part to obtain granules.

Example 15 6 parts of powder compound NQ115, 36 parts of clay, 6 parts of Merck
0 parts and 1 part of isopropyl phosphate,
A powder is obtained by pulverizing and mixing with an atomizer of q=N12.00 Orpm.

Example 16 30 parts of the emulsion compound tJn 146, 60 parts of xylene and Solbol'-5M100 (a surfactant from Toho Chemical Co., Ltd. containing a mixture of a nonionic surfactant and an anionic surfactant) An emulsion was obtained by dissolving 10 parts of the product (trade name).

(3) Effects of the invention Next, the herbicidal effects of the compounds of the present invention will be shown in test examples.

Test Section IJ 1 Flooded soil treatment herbicidal test 1/15,
Paddy soil is crystallized in a 500 are porcelain pot, and the surface is... Seeds of Japanese wildflower, firefly, cyperus japonica, Japanese cypress, and Kikashigusa were uniformly sown in the j part, and after flooding to a depth of 2 cm, two paddy rice seedlings at the two-leaf stage (product quantity: Hifuji) were transplanted.

One day later, a sufficient amount of the diluted solution of the irrigation agent obtained according to Example 111 was dropped onto the water surface for treatment. Thereafter, the pots were kept in a greenhouse and watered for 1 hour.

20 days after the chemical solution treatment, the herbicidal effect and the degree of phytotoxicity of paddy rice were examined using the following criteria. This test example was conducted using a 1-dose, 6-bottle system, and the average value was determined. The results are shown in Table 2.

Weeding effect.

5: Killing rate of 95% or more F ~ Complete withering 4: Killing rate of M * 80 or more l-, ~ less than 95 3: Weed killing rate 50
2: Weed killing rate of 30% or more - less than 50 inches Course 1: Weed killing rate of 10 inches or more - less than 60 inches ) +: Moderate damage (leaf blight) + - Severe damage (growth suppression) ++: Jinkutsu (withering) Table 2 zb 2 5 2
2 3tz 4 b
2 5 5104 50
−5 5 j 4
4j07 50-4 5
3 5 5109 50
- 4 5 4 5'
425 ゛ 34342 115 50 '-55355255,52
55 12250-543” 4 4L51
50-3 5 3
5 52b2 4 1 3
2160 50'-34354L, 25
The 01LJ11 comparative drug has the following chemical structure, and was formulated and tested in the same manner as the compound of the present invention.

([Ch, em, Abstr, J Vol. 82 No. 1643
(Compound described in 8000) (Chem, Abstr, J LOL Vol. 71, No. 79026
Compounds described on page f) ○ (“chom, Abstr, J Volume 88 i'1207
Compound described on page 23b) ([Chem, Abet, r, J Chiku 68, 3453
'6 Compounds of 1) ([Chem, Abstr, J Vol. 41, No. 3902-3
9j3C Page Bandit's Compound) (JChem, Abstr, j Vol. 71 No. 101493
Compounds on page j)

Claims (1)

[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ {In the formula, R represents a hydrogen atom, a lower alkyl group, or a chlorine atom, m represents an integer of 1 or 2, and R^ 1 represents a lower alkyl group or lower alkenyl group, R^2 represents a lower alkyl group, lower alkenyl group, formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X is a lower alkyl group, a halogen atom, a lower alkoxy group or trifluoromethyl group, and n is an integer of 0, 1, 2, or 3). ) group, α-methylbenzyl group, α,
α-dimethylbenzyl group or tetralinyl group,
and R^3 represents a hydrogen atom or a lower alkyl group,
Alternatively, R^2 and R^3 have 4 to 6 carbon atoms and can form a saturated ring.] An arylsulfonyl fatty acid amide derivative. 2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R, m and R^1 have the meanings described below) and the arylsulfonyl fatty acid derivative or its reactive derivative and the general formula ▲ Numerical formula, There are chemical formulas, tables, etc. ▼ A general formula characterized by reacting with an amine derivative represented by (in the formula, R^2 and R^3 have the meanings described below) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ {In the formula, R represents a hydrogen atom, a lower alkyl group, or a chlorine atom, m represents an integer of or 2, R^1 represents a lower alkyl group or a lower alkenyl group, and R^2 represents a lower alkyl group , lower alkenyl group, formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein, (represents an integer), formula ▲ Numerical formula, chemical formula, table, etc. ▼ (in the formula, p represents an integer of 0, 1 or 2) group, α-methylbenzyl group, α,
α-dimethylbenzyl group or tetralinyl group,
and R^3 represents a hydrogen atom or a lower alkyl group,
Alternatively, R^2 and R^3 have 4 to 6 carbon atoms and can form a saturated ring.] A method for producing an arylsulfonyl fatty acid amide derivative. 3) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ {In the formula, R represents a hydrogen atom, a lower alkyl group, or a chlorine atom, m represents an integer of 1 or 2, and R^1 represents a lower alkyl group or Indicates a lower alkenyl group, R^2 is a lower alkyl group, lower alkenyl group, formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein, X is a lower alkyl group, halogen atom, lower alkoxy group, or trifluoromethyl group) and n represents an integer of 0, 1, 2, or 3), a group of the formula ▲ has a mathematical formula, a chemical formula, a table, etc. ▼ (in the formula, p represents an integer of 0, 1, or 2), α-methylbenzyl group, α,
α-dimethylbenzyl group or tetralinyl group,
and R^3 represents a hydrogen atom or a lower alkyl group,
Alternatively, R^2 and R^3 have 4 to 6 carbon atoms and can form a saturated ring.] A herbicide characterized by comprising an arylsulfonyl fatty acid amide derivative as an active ingredient.