DD236668A5 - HERBICIDAL COMPOSITION - Google Patents

Abstract

The invention relates to herbicidal compositions containing D-1,2,4-triazolin-5-one derivatives as an active ingredient. Described are D2-1,2,4-triazolin-5-one derivatives represented by the general formula I wherein R is a hydrogen atom; an alkali metal atom; a quaternary ammonium salt; an unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted alkyl group having halogen atoms as substituents; an unsubstituted cycloalkyl group; a substituted cycloalkyl group having halogen atoms as substituents; an alkenyl group; an alkynyl group; a lower alkoxyalkyl group; a lower alkylthioalkyl group; a lower alkylsulfinylalkyl group; a lower alkylsulfonylalkyl group; a lower alkoxyalkyl group; a lower alkoxycarbonylalkyl group; Hydroxycarbonylalkylgruppe; an unsubstituted benzyl group; a substituted benzyl group having 1 to 2 substituents selected from the group of a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a hydroxycarbonyl group and a phenoxy group; is an α-methylbenzyl group or a phenethyl group, as an active ingredient with suitable carriers in herbicides. Formula I

Description

CH ₃ "

wherein R is a hydrogen atom; an alkali metal atom; a quaternary ammonium salt; an unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted alkyl group having halogen atoms as substituents; an unsubstituted cycloalkyl group; a substituted cycloalkyl group having halogen atoms as substituents; an alkenyl group; an alkynyl group; a lower alkoxyalkyl group; a lower alkylthioalkyl group; a lower alkylsulfinylalkyl group; a lower alkylsulfonylalkyl group; a lower alkoxyalkoxyalkyl group; a lower alkoxycarbonylalkyl group; a hydroxycarbonylalkyl group; an unsubstituted benzyl group; a substituted benzyl group having 1 to 2 substituents selected from the group of a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a hydroxylcarbonyl group and a phenoxy group; an α- methylbenzyl group or a phenethyl group, as an active ingredient with suitable carriers. 2. The herbicidal composition according to item 1, wherein the active ingredient is A ² -1,2,4-triazolin-5-one derivatives.

Field of application of the invention

The invention relates to herbicidal compositions containing A ² -1,2,4-triazo-in-5-one derivatives as an active ingredient.

Characteristic of the known technical solutions

Some similar compounds which are related to the A ² -1,2,4-triazolin-5-one derivatives represented by the general formula (I) are described as active ingredient in herbicidal compositions disclosed in U.S. Pat Japanese Patent Publication Nos. Sho 57-108079 and Sho 57-181069.

Object of the invention

The aim of the invention is to find herbicidal compositions which require relatively low active substance concentrations and also have low phytotoxicities.

Explanation of the essence of the invention

The invention has for its object to provide novel herbicidal compositions containing as active ingredient new 1,2,4-triazolin-5-one derivatives.

According to the invention, it has been found that compounds represented by the general formula (I)

N ^N - ^CHF 2

(I) CH ₃

wherein is pure hydrogen atom; an alkali metal atom; a quaternary ammonium salt; an unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted alkyl group having halogen atoms as substituents; an unsubstituted cycloalkyl group; a substituted cycloalkyl group having halogen atoms as substituents; an alkenyl group; an alkynyl group; a lower alkoxyalkyl group; a lower alkylthioalkyl group; a lower alkylsulfinylalkyl group; a lower alkylsulfonylalkyl group; a lower alkoxyalkoxyalkyl group; a lower alkoxycarbonylalkyl group; a hydroxycarbonylalkyl group; an unsubstituted benzyl group; a substituted benzyl group having 1 to 2 substituents selected from the group of a halogen atom, a lower alkyl group, a

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a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a hydroxycarbonyl group and a phenoxy group; an α-methylbenzyl group or a phenethyl group, can be used as an active ingredient in herbicides.

Compounds represented by the general formula (I) can be produced, for example, by the following method A, method B and method C:

Method A

τ "r \ 1

CHF ₂ -Z

(III)

, Cl

base

(I'D

(wherein R is as defined above; Z ^{1 is} a chlorine atom, a bromine atom or an iodine atom). Method B

N-CHF.

Il

ROCCH-Z ^- CH,

Base (IV)

(wherein R is as defined above, Z ^{2 is} a halogen atom).

CH.

Method C

RAW (VI)

ΟΙΟ

II

ROCCHO CH,

F O

N-CHF

CH

(VII)

(D

(wherein R is as defined above; X is a halogen atom or a hydroxyl group).

Thus, the present Δ ² -1 →, A-triazolin-S-on derivatives represented by the general formula (I) can be prepared by the method A, by reaction of a compound represented by the general formula (II) with a compound represented by the general formula (III); according to the method B, by reaction of a compound represented by the general formula (IV) with a compound represented by the general formula (V); and by the method C, by reacting a compound represented by the general formula (VII) with a compound represented by the general formula (VI), each in an inert solvent, in the presence or absence of a basic compound.

As the inert solvent used in these reactions, any inert solvent which does not adversely affect the reaction can be used, for example, aromatic hydrocarbons such as benzene, toluene, xylene or the like; for example, aliphatic hydrocarbons such as n-hexane, cyclohexane or the like; for example, alcohols such as methanol, ethanol, propanol, ethylene glycol or the like; for example, ketones such as acetone, methyl ethyl ketone, cyclohexanone or the like; for example, lower aliphatic acid esters such as ethyl acetate or the like; for example, ethers such as tetrahydrofuran, dioxane or the like; for example, lower fatty acid amides such as dimethylformamide, dimethylacetamide or the like; and for example, water, dimethylsulfoxide or the like. The above-mentioned solvents may be used alone or in admixture thereof.

In addition, in the method C, when an alcohol is used as the solvent, it is preferable to use an alcohol corresponding to a compound represented by the general formula (VI).

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The basic compounds used in the above reactions are, for example, inorganic basic compounds, for example, alkali metal hydrides, such as sodium hydride or the like: alkali metal hydroxide, such as sodium hydroxide, potassium hydroxide or the like; Alkali metal carbonates such as sodium carbonate, potassium carbonate or the like; Alkali metal hydrogencarbonate such as sodium hydrogencarbonate, potassium hydrogencarbonate or the like; Alkali metal alcoholate, such as sodium methylate or the like; and organic basic compounds such as pyridine, trimethylamine, triethylamine, diethylaniline, 1, S-diazabicyclo-tBAOJ-T-undecene or the like.

For example, the reactions may be carried out at a temperature in the range of 0 to 150 ° C up to a predetermined temperature.

The reactions are equimolar reactions at each stage, and in carrying out these reactions, a slight excess of one reaction component relative to the other reaction component can be used.

The reaction time can be selected in the range of 0.5 to 48 hours.

After completion of the reaction, the respective product can be obtained by treating the reaction product in a conventional manner.

The compound represented by the general formula (II) used as the starting material in the method A can be prepared by the following reaction steps:

NHNH

R ¹ -AC = NCOOR ²

^CH

(IX)

heat

(VIII)

NHNHC = NC00R

basic compound

(II)

(wherein R is as defined above; R ¹ and R ^{2 are} each a lower alkyl group; A is an oxygen atom or a sulfur atom). ··

Thus, a compound represented by the general formula (II) can be prepared by reacting a compound,

represented by the general formula (VIII), with a compound represented by the general formula (IX) in an inert solvent with heating, whereupon the thus-obtained compound represented by the general formula (X) undergo ring-closing reaction is treated with a basic compound while being separated from the reaction product or not.

Moreover, a compound represented by the general formula (IV) used as the starting material in the method B can be prepared by the following reaction step:

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N-CHF-

HBr

(XI) (IV)

(wherein R ^{1 is} as defined above).

In the above-mentioned reaction, instead of using hydrobromic acid, hydriodic acid or

an alkyl thiolate can be used.

Typical examples of Δ ² -1- ^ -triazoline-B-on derivatives represented by the general formula (I) are shown in U.S.P.

Table 1 below.

table

Connection number.

1 2 3 4 5 6 7 8 9 10 11 12 13 14

H-

N / A-

K-

JSO-C ₃ H ₇ ^ NH ₃ - (C ₂ H ₅ ) ^ H-

CH ₃ -C ₂ H ₅ -HC ₃ H ₇ - JSO -C ₃ H ₇ -

iso -C.Hg tert -C ₄ Hg- physical properties

up ⁴ · ⁵ 1.5192 Melting point 186.1 ⁰ C S. Melting point ^: 119.2 ° C Melting point 92.7 ⁰ C Melting point 157.3 ⁰ C Oily substance Melting point

23

η ¹⁰

126.5 ⁰ C

1.5142 1.5112 1.5051

n * ³ ' ⁰ 1.5051 nl ⁹ - ⁰ 1.5031 η * ⁹ ' ⁰ 1.5011 n ^ ⁶ · ⁰ 1.5009

-Forts.

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Table 1 (cont.)

ClCH ₂ CH ₂ - 2 ' BrCH ₂ CH ₂ - CH ₂ CH ₂ Cl ₃ CCH ₂ - CH ₂ CH ₂ F ₃ CCH CH- ClCH ₂ CH ₃ BrCH ₂ CHCH ₉ - ClCHp ClCH ₂

π ' .4984 n_ * 1 .5002 n_. 1 · .4992 K | 26 «5 1.5204 N ¹⁹ * ⁵ 1.5291 Mp 106.5 ⁰ C.

19.5 D

1.4826

Melting point 87.7 C melting point 83.8 ⁰ C melting point 68.7 ° C

Melting point 95.0 C

Cl

ClCH, ClCH.

CH-nj ⁴ * ⁵ 1.5091

BrCH,

BrCH,

CH melting point 104.2 ° C

CH-nj ⁹ * ⁵ 1.4573

29 ClCH ₂ CH ₂ CH ₂ CH ₂ melting point 95.3 C

0-

CH ₂ = CHCH ₂ -26.0,

 n_ l.

P-7

1.5140 ny ⁷ · ⁵ 1.5174

28.5

l.

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Table 1 (cont.)

34 .CH = CCH ₂ 35 CH 1 CCH ₂ CH ₂ - 36. CH ₃ O (CH ₂ ) ₂ - 37 C ₂ H ^ (CH ₂ ) ₂ - 38 JSO-C ₃ H ₇ O (CH ₂ ) ₂ - 39 BC ₄ H ₉ O (CH ₂ ) ₂ - 40 CH.OCHCH-CH., - 3 ι 2 2 I CH ₃ 41 CH ₃ SCH ₂ - 42 CH ₃ S (CH ₂ J ₂ - 43 C ₂ H ₅ S (CH ₂ ) ₂ - 44 ISO-C ₃ H ₇ S _{(CH2) 2} ~ 45 ISO-C ₄ H ₉ S (CH ₂ ) ₂ - 46 Sec-C ₄ H ₉ S (CH _{2) 2} - 47 tert-CH ₀ S (CH ₀ ) - 48 CH ₃ S (CH ₂ J ₃ - 49 C ₂ H ₅ S (CH ₂ ) ₃ - 50 ISO-C ₃ H ₇ S (CH ₂ ) ₃ - 51 HC ₄ H ₉ S (CH ₂ ) ₃ - 52 ISO-C ₄ H ₉ S (CH ₂ ) ₃ - 53 tert-C ₄ H ₉ S (CH ₂ J ₃ 54 CH ₃ S (CH ₂ ) ₂ - O 55 CHS ^ (CH ₂ ), -

0 0

CH ₃ O (CH _{2) 2} O (CH ₂₎ n ^ ⁸ * ^{5 7} * nj 1.5192 ⁵ 1.5209 n ^ ^{6 '0} 1.5088 n ^ ⁶ · ⁰ · ⁰ 1.5022 1.4989 1.4878 · ⁰ · ⁵ 1.5009

ni ⁸ · ⁰ 1.5279

D 26.5

D -

19.5

1.5306 1.5274

19.5

19.5 '

19.5

22.5

19.5

19.5

19.5

14.5

14.5

16.5

Melting point 104.5 ° C

1.5233 1.5212 1.5219 1.5179 1.5299 1.5203 1.5204 1.5216 1.5209 1.5172

Melting point 99.8 ⁰ C

n £ ⁶ * ⁰ 1.5052

- Forts. -

Table 1 (cont.)

CH-, OC-CH- ³ I! I 0 CH _n melting point 108.1 ⁰ C

CH ₂ -

Cl CH "-

Cl

Melting point 82.4 ⁰ C 117.5 ⁰ C melting point melting point of 72.6 ⁰ C

Cl

CH - melting point 73.0 ⁰ C

Mp 115.7 ⁰ C.

-o-melting point 80.0 ⁰ C

H ₃ C

-O-

CH ₂ melting point 102.8 ⁰ C

H ₃ CO

-O-

CH ₂ melting point 89.4 ⁰ C

Melting point 126.5 ⁰ C

CH ₅ OC - ^ _ 7 ~ CH ₂ - melting point 135. 3 ⁰ C

CH ₂ -1.5588

Cl

Cl- V ^ -CH ₂ melting point 163.0 ⁰ C

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- Forts. -

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Table 1 (cont.)

Mp 114.7 ⁰ C.

Melting point 96.5 ⁰ C oily substance

CH ₂ CH ₂ -

oily substance

Table 2 below gives the data of the NMR spectrum of compounds whose physical properties are referred to as "oily substance".

Table 2

Connection no.

. ' CCI ₄

NMR (ppm)

TMS

1.15 (t, 9H), 1.64 (d, 3H), 2.41 (s, 3H), 2.19 (q, 6H), 4.53 (q, 1H), 7.03 (t, 1H), 7.04 (d, 1H), 7.22 (d, 1H)

1.32-1.77 (m, 6H), 2.30 (s, 3H), 4.60 (q, 1H), 5.76 (q, 1H), 686 (t, 1H), 6.76-7.31 (m, 7H)

1.56 (d, 3H), 2.35 (s, 3H), 2.84 (t, 2H), 4.28 (t, 2H), 4.59 (q, 1H), 6.91 (t, 1H), 6.85-7.32 (m, 7H)

embodiment

The following examples serve to illustrate the preparation of the compounds used according to the invention as active ingredient in herbicides, without restricting them.

example 1

Preparation of 1- (4-Chloro-2-fluoro-5- [1- (ethoxycarbonyl) -ethoxy] -phenyl) -4-difluoromethyl-3-methyl-A ² -1,2,4-triazolin-5-one (Comp No.9).

Cl-HO

CH, - CHF ₂ BrCHCOOC ₂ H ₅

Cl

N-CHF,

CH,

(IV)

H ₅ C ₂ OCCHO CH,

13.27 g (0.045 mol) of the compound (IV) 9.06 g (0.0498 mol) of ethyl a-bromopropionate and 13.27 g (0.0962 mol) of potassium carbonate were refluxed in 200 ml of acetone with stirring for 3 hours. Subsequently, the reaction mixture was cooled to room temperature and the insoluble materials were removed by filtration. Then, the filtrate was concentrated, and the oily substance thus obtained was dissolved in diethyl ether and washed with cold water, whereupon the diethyl ether solution was dried, the solvent was removed by evaporation, and an oily substance was obtained. (This oily substance was purified as such by chromatography on a dry column using silica gel.) Yield 14.7 g (83.1%) Calculation index nj ⁹⁰ 1.5112.

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Example 2

Preparation of 1- (4-Chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl) -4-difluoromethyl-3-methyl-A ² -1,2,4-triazolin-5-one (Compound no. 1)

F O

CHOCCHO CH,

-CHF,

, -4 i

^f \\ _ H ^ N-CHF,

C ₂ H ₅ OCCHO CH,

CH.

1.4g (0.00356 mol) 1- (4-chloro-2-fluoro-5- [1- (ethoxycarbonyl) -ethoxy] -phenyl) -4-difluoromethyl-3-methyl-A ² -1,2 , 4-Triazolin-5-one were dissolved in 50 ml of ethanol and then 1.2 g of 20% aqueous potassium hydroxide solution was added to this solution, and the whole mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction mixture was poured into ice-water, acidified with hydrochloric acid, and then the desired product was extracted with ethyl acetate. The extract was washed with water and dried with anhydrous magnesium sulfate, whereupon the solvent was removed by evaporation and 1.1 g of an oily substance was obtained as the desired product. Calculation index n ² , ⁴ · ⁵ 1.5192. Yield 84%.

Example 3

Preparation of Sodium 2- [2-chloro-5- (4-difluoromethyl-3-methyl-5-oxo-A ² -1,2,4-triazolin-1-yl) -4-fluorophenoxy] -propionate (Compound No. 2).

N-CHF,

CH,

CH,

0.5g (0.00136 mol) 1- {4-Chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1,2,4 Triazolin-5-one was dissolved in 20 ml of tetrahydrofuran, and to this solution was added 0.05 g (0.00125 mol) of sodium hydride, and the whole mixture was stirred at room temperature for 10 minutes. After completion of the reaction, the tetrahydrofuran was removed by evaporation under reduced pressure, and the residue thus obtained was washed with η-hexane to give 0.37 g of the desired compound. Mp 186.1 ° C. Yield 76.4%.

Example 4

Preparation of dibutylammonium 2- [2-chloro-5- (4-difluoro-methyl-3-methyl-5-oxo-A ² -1,2,4-triazolin-1-yl) -4-fluoro-phenyloxy] Propionate (Compound No.7).

0.5 g (0.00136 mol) of 1- {4-chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-A ² -1,2,4-triazoline 5-on was dissolved in 20 ml of benzene, and 1.0 g (0.0139 mol) of dibutylamine was added to the solution, followed by carrying out the reaction under ice-cooling. The crystals formed in the reaction mixture were collected by filtration and washed with benzene to give 0.51 g of the desired compound. Mp 126.5 ⁰ C. Yield 79.4%.

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Example 5

Preparation of! - {^ Chloro-fluoro-B-ti-lpropargyloxycarbony O-ethoxyl-phenyl-1-yl-difluoromethyl-S-methyl-A ^ I ^ atriazolin-S-one (Compound No. 34).

N CHF

CH.

HC = CCH ₂ OCCHo CH,

A mixed solution of 20 ml of thionyl chloride containing 2.7 g of 1- {4-chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1, 2,4-triazolin-5-one was refluxed with heating for 2 hours. After completion of the reaction, the excess thionyl chloride was removed by evaporation, to give 2.8 g of 1- {4-chloro-2-fluoro-5- [1- (chlorocarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl -A ² -1,2,4-triazolin-5-one quantitatively. Subsequently, 0.5 g (0.0013 mol) of this compound was dissolved in 20 ml of tetrahydrofuran, and to this solution were added 0.2 g (0.00357 mol) of propargyl alcohol and 0.2 g (0.00198 mol) of triethylamine, and the whole mixture was allowed to stand for 2 hours reacted at room temperature. After completion of the reaction, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed by evaporation with an aqueous solution containing 10% of potassium carbonate. The resulting residue was purified by dry column chromatography to give 0.35 g of the desired compound. Refractive index n ² , ⁸ · ⁵ 1.5192. Yield 66.6%.

Example 6

Preparation of 1- {5- [1- (tert -butoxycarbonyl) -ethoxy] -4-chloro-2-fluorophenyl} -4-difluoromethyl-3-methyl-A ² -1,2,4-triazolin-5-one (Compound No. 14).

FO FO

N-CHF.

CH-

(CH ₃ ) ^ COCCHO CH-,

0.58 g (0.00151 mol) of 1- {4-chloro-2-fluoro-5- [1- (chlorocarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1,2, 4-triazolin-5-one was added to a mixed solution of 0.25 g (0.00338 mol) of tert-butyl alcohol, 0.14 g (60% in oil, 0.0035 mol) of sodium hydride and 20 ml of tetrahydrofuran. The entire mixture was refluxed for 6 hours. After complete reaction, the reaction mixture was treated under conditions similar to those described in Example 5 to give 0.13 g of the desired product. Refractive index n§ ⁶ · ⁰ 1,5009. Yield 18.8%.

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Example 7

Preparation of 1- {4-chloro-2-fluoro-5- [1 - [[1- (methoxycarbonyl) ethoxy] carbonyl] ethoxyphenyl} -4-difluoromethyl-3-methyl-A ² -1,2, 4-triazolin-5-one (Compound No. 57).

N-CHF.

CH.

CH-OCCHOCCHO

³ II

CH ₃ CH ₃

A mixed solution of 0.5 g (0.00136 mol) of 1- {4-chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1 , 2,4-Triazolin-5-one, 0.28 g (0.00136 mol) N, N'-dicyclohexylcarbodiimide, 0.02 g (0.000164 mol) of 4-dimethylaminopyridine and 10 ml of diethyl ether were reacted at room temperature for 6 hours. After completion of the reaction, the insoluble materials were removed by filtration, and the filtrate was evaporated, and the resulting residue was purified by dry column chromatography to give 0.41 g of the desired compound. Mp 108.1 ⁰ C. Yield 64.3%.

Example 8

Preparation of 1- {4-Chloro-2-fluoro-5- [1- (ethoxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1,2,4-triazolin-5-one (Compound No. 9).

FO FO

H/ jT

N NH S * Cl / yN

CH..OCCHO ^{2 5} I

CH,

C ₂ H ₅ OCCH

0.046 g (0.00134 mol) of sodium hydride were suspended in 10 ml of dried N, N-dimethylformamide and to the suspension was added a solution prepared by dissolving 0.4 g (0.00122 mol) of 1- {4-chloro-2-fluoro 5- [1- (ethoxycarbonyl) -ethoxy] -phenyl} -3-methyl-A ² -1,2,4-triazolin-5-one, added dropwise at room temperature. After the dropwise addition, the whole mixture was stirred for 30 min, and then monochloride fluoromethane gas (CICHF ₂₎ 5 h at 130 ⁰ C was passed into the mixture. After completion of the reaction, the reaction mixture was cooled to room temperature, and the reaction mixture was poured into ice-water. The formed oily substance was extracted with diethyl ether, and the extract was dried with anhydrous magnesium sulfate. The solvent was removed by evaporation to give an oily substance. This oily substance was purified by dry column chromatography to give 0.15 g of the desired compound. Refractive index nj ⁹ 1.5112. Yield 32.6%.

Example 9

Preparation of iW-chloro-fluoro-S-II-imidylthiomethoxycarbonyl-ethoxy-J-phenylM-difluoromethyl-S-methyl-A ² - (tri-zolin-5-one, Compound No. 41).

N-CHF,

Cl O

CH ₃ SCH ₂ OCCHO

N CHF. \ /

CH.

A mixture of 0.5 g (0.00137 mol) of 1- {4-chloro-2-fluoro-5- [1- (hydroxycarbonyl) -ethoxy] -phenyl} -4-difluoromethyl-3-methyl-A ² -1, 2,4-triazolin-5-one, 1.76 g (0.00128 mol) of tert-butyl bromide, 1.15 g (0.00137 mol) of sodium hydrogencarbonate and 10 ml of dried dimethyl sulfoxide were reacted with stirring at room temperature for 32 hours. After completion of the reaction, the reaction product was treated by a procedure similar to that of Example 8 to give 0.4 g of the desired compound. Calculation index no ⁸⁰ 1,5279. Yield 68.7%.

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The A ² -1,2,4-triazolin-5-one derivatives are suitable according to the invention for controlling annual and perennial weeds in paddy fields, higher fields, orchards and swamps, such as barnyardgrass (Echinochloa crusgalli Beauv., A one-year weed of the Family of Gramineae, which grows in rice fields and is very harmful), Monochoria (Monochoria vaginalis Presl, a highly harmful annual herb of the Pontederiaceae family that grows in rice fields), small-flowered umbrella plant (Cyperus difformis L, a harmful annual herb of the family the Cyperaceae that grows in rice fields), slender spikerush (Eleocharis acicularis Römer et Schultes, a typical harmful perennial weed of the family Cyperaceae that grows in rice fields, and also grows in swamps and waterways), arrowhead (Sagittaria pygmaea Mig., A harmful perennial weed of the family Alismataceae, d which grows in rice fields, swamps and ditches), Bulrush (Scirpus juncoides Roxb. var. Hotarui Ohwi, a year old Cyperaceae weed that grows in paddy fields, swamps and ditches), wild oats (Abena fatua L, a one-year weed of the Gramineae family that grows on plains, uncultivated land and higher fields), Mugwort (Artemisia princeps Pamp., A perennial weed of the Compositae family that grows in cultivated and uncultivated fields), large fingergrass (Digitaraia adscendcus Henr., A one year old weed of the family Gramineae, which is a typical highly harmful weed found in Gishi-gishi (Rumex japonicus Houttuyn, a perennial weed of the Pcriygonaceae family that grows in higher-altitude fields and along roadsides), umbrella reed grass (Cyperus iria L., a one-year weed of the Cyperaceae family Growing on higher fields and along roadsides) Red Roan Foxtail (Amaranthus varidis L., an egg annual weed of the Amaranthaceae family, which grows in higher-altitude fields, in fallow land and along roadsides), and Spitzklette (Xanthium strumarium L., a one-year weed of the Compositae family, which is severely harmful to soybeans). Since the Δ ² -1 ^^ - triazoline-B-on derivatives represented by the general formula (I) have excellent weed control activity, both at the pre-emergence and post-emergence stage, they are useful as herbicides for the treatment of soils before and after sowing (plants), for the treatment of soils in the growing season, for foliar treatment before sowing (plants), foliar treatment in the growing season of useful highland crops such as soybeans, cotton, cereals and maize like that. In addition, these derivatives are useful as herbicides used in rice fields in the initial stage as well as in the middle stage of rice growth and, moreover, are useful as herbicides for controlling general weeds, for example, on ridges between rice fields, agricultural roads, waterways, pastures , Cemeteries, parks, roads, playgrounds, unused land around buildings, reclaimed land, railway tracks and forests. The herbicidal treatment of such areas is most effectively and economically carried out when the weeds have not risen, but it is not necessarily carried out before the emergence of the weeds.

For applying the derivatives of the invention as herbicides, they are generally formulated by conventional methods for producing agricultural compositions to a form suitable for use. Thus, according to the invention, the derivatives are mixed with suitable inert carriers and, if necessary, further with additives in an appropriate ratio and prepared by dissolution, dispersing, suspending, mechanical mixing, impregnation, adsorption or adhesion to prepare a mixture for a suitable form of composition , z. As suspensions, emulsifiable concentrates, solutions, "wettable powders, dusts, granules or tablets.

The carriers used in the agricultural compositions can be either solid carriers or liquid carriers. Examples of useful solid carriers include vegetable powders such as soybean meal, cereal flour, wood flour, bark flour, sawdust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose and extraction residues of plants; fibrous materials such as paper, corrugated board and waste materials, synthetic polymers such as powdered synthetic resins; inorganic or mineral products such as clays (e.g., kaolin, bentonite, and acid clay), talc products (e.g., talc and pyrophyllite), silica products (e.g., diatomaceous earth, silica sand, mica, and white carbon) dispersed synthetic silicic acid, also referred to as finely powdered hydrated silica or hydrated silicic acid, and some commercial products contain calcium silicate as main ingredient]), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground bricks, fly ash, sand, calcium carbonate and calcium phosphates; chemical fertilizers, ammonium sulfate, ammonium phosphates, ammonium nitrate, urea, and ammonium chloride; and natural fertilizers. These solid carriers may be used alone or in combination with one another. Useful liquid carriers may be selected from those which are solvents for the active ingredients, and such which are not solvents, but can disperse the active ingredients by means of additives. Examples of these liquid carriers which can be used alone or in combination with each other are water, alcohols (eg, methanol, ethanol, isopropanol, butanol and ethylene glycol), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers (eg Diethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbons (e.g., gasoline and mineral oils), aromatic hydrocarbons (e.g., benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene), halogenated hydrocarbons (e.g. Dichloroethane, chlorinated benzenes, chloroform and carbon tetrachloride), esters (e.g., ethyl acetate, dibutyl phthalate, diisopropyl phthalate and dioctyl phthalate), acid amides (e.g., dimethylformamide, diethylformamide and dimethylacetamide) and nitriles (eg, acetonitrile) and dimethylsulfoxide.

The adjuvants, examples of which are given below, are used according to the individual purposes. In some cases, they are used in combination. In some cases, no adjuvant or additive is used at all.

Surfactants may be used to emulsify, disperse, solubilize and / or wet the active ingredients, for example, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resminates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate , Alkylarylsulfonates, naphthalenesulfonic acid condensation products, lignosulfonates and higher alcohol sulfate esters. For the stabilization of dispersion, tackification and / or agglomeration of the active ingredients, the following materials may be used, for example: casein, gelatin, starch, alginic acid, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohol, pine root oil, rice bran oil, bentonite and lignosulfonates.

-13- 755 19

To improve the flowability of the solid compositions, it is advisable to use waxes, stearates or alkyl phosphates.

As the peptizer for dispersible compositions, it is also recommended to use naphthalenesulfonic acid condensation products and condensed phosphates.

It is also possible to use anti-foaming agents, such as a silicone oil.

The content of active ingredients in the herbicidal composition may be adjusted depending on the purpose of use. In general, 0.5 to 20% by weight of the active ingredients can be used to prepare powdered or granulated products, and 0.1 to 50% by weight of the active ingredients can usually be used to prepare emulsifiable concentrates or wettable powder products ,

To destroy various weeds, to inhibit their growth or to protect crops from damage caused by these weeds, the herbicidal composition of the present invention is used in a weed killing or weed growth inhibiting dosage, as such or after appropriate dilution after suspending in water or other medium, on the soil or on the leaves of the weeds in the areas where the growth or growth of the weeds is undesirable.

The amount of the herbicidal composition according to the invention to be used depends on various factors such as the purpose of use, the respective weeds, the emergence or growth state of the weeds and crops, the weed tendency of the weeds, the weather Environmental conditions, the form of the herbicidal composition, the order mode, the type of the field to be treated and the time of use and other aspects.

In applying the herbicidal composition of the present invention alone as a selective herbicide, it is preferable to select the dosage of 1 to 500 g per 100 ares. On the other hand, when the herbicidal composition of the present invention is applied in combination with herbicides, its optimum dosage is often lower than that of a single use, and the present herbicidal composition can be used in an amount less than the above when used in combination with a herbicide other herbicide type is used.

The herbicidal composition according to the invention is particularly valuable for the pre-emergence and first-ever casserole treatment of higher altitude fields and for the early stage and middle stage weed control of weeds. In order to be able to expand both the range of the weed species which can be combated and the period of effective use, or to be able to reduce the dosage, the herbicidal composition according to the invention can be used in combination with other herbicides, and this use is within the scope of the present invention.

For example, the herbicidal composition of the present invention may be used in combination with one or more of the following herbicides.

Phenoxy fatty acid type herbicides: for example, 1,4-D: e.g. Ethyl (2,4-dichlorophenoxy) -acetate MCP: e.g. For example, ethyl (2-methyl-4-chlorophenoxy) acetate, sodium (2-methyl-4-chlorophenoxy) acetate and allyl 2- (2-methyl-4-chlorophenoxy) acetate

MCBP: e.g. Ethyl (2-methyl-4-chlorophenoxy) butyrate '"·

Diclofop-methyl: methyl 2- [4-2,4-dichlorophenoxy) -phenoxy] -propionate

Diphenyl ether type herbicides: for example, nitrogen: 2,4-dichlorophenyl-4-nitrophenyl ether Chloronitrofen: 2,4,6-trichlorophenyl 4-nitrophenyl ether

Chloromethoxynil: 2,4-dichlorophenyl-3-methoxy-4-nitrophenyl ether

Acifluorfen: 5- (2-chloro-a, a, a-trifluoro-p-tolyoxy) -2-nitrobenzoic acid and its salts Flu.azifop-butyl: Butyl - (+) - 2- [4 [5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] propionate Triazine type herbicides: for example, simazine: 2-chloro-4,6-bis (ethylamino) -s-triazine Prometryne: 2-methylthio-4,6-bis ( isopropylamino) -s-triazine

Simetryn: 2-methylthio-4,6-bis- (ethylamino) -s-triazine and

Metribuzin: 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5 (H) -one

Carbamate-type herbicides: for example, molinate: s-ethyl-hexahydro-IH-azepine-1-carbothioate Swep: methyl. N- (3,4-dichlorophenyl) carbamate

Chloropropham: isopropyl N- (3-chlorophenyl) carbamate and

Benthiocab: s- (4-chlorobenzyl) -diethyl-triocarbamate

Toluidine-type herbicides: for example, trifluralin: (a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine) and · pendimethalin: N- (1-ethylpropyl) -2,6-dinitro- 3,4-xylidine

Acid amide type herbicides: for example propanil: 3,4-dichloropropionanilide butachlor: N- (butoxymethyl) -2-chloro-2,6-diethyl-acetanilide

Alachlor: 2-Chloro-2,6-diethyl-N- (methoxymethyl) -acetanilide

Metolachlor: 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (2-methoxy-1-methylethyl) -acetamide and pretilachlor: 2-chloro-2,6-diethyl-N- (2-propoxyethyl ) -A'-entamlid

Other herbicide types: for example

Duron: 3- (3,4-dichlorophenyl) -1,1-dimethy! Urea

Bentazone: 3-isopropyl (H) -2,1,3-benzothiazine-4- (3H) -one-2,2-dioxide

Pyrazolate: 4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yl p-toluenesulfonate

Pyrazoxyfen: 1,3-dimethyl-4- (2,4-dichlorobenzoyl) -5-phenacyloxypyrazole and

MY-71: 4- (2,4-bichloro-3-methylbenzoyl) -1,3-dimethyl-pyrazol-5-yl-p-toluenesulfonate The following examples illustrate the herbicidal and herbicidal compositions of the invention. However, these examples are not intended to be limiting.

-14- / OO 13

Herbicidal Test Example 1.

Control action of weeds in pre-emergence stage in paddy fields:

Pots (V10000Ar) were filled with soil to simulate a paddy field and planted with weeds of millet, monochoria, umbrella plant and bulrushes, all of which are weedy weeds in paddy fields, and conditioned so that Pre-emergence state was achieved.

The soil in the pot was treated by spraying with each of the present compounds (listed in Table 1) formulated to give a given liquid concentration. After 21 days, the percentage control of weed growth was compared with that of an untreated pot, and the herbicidal activity was determined according to the criterion shown in Table 2 below.

Table 2

Criterion for the determination of herbicidal activity

Extent of

herbicidal

effect

percent control of weed growth

100

90-99

80-89

70-79

wenigerals70

The test results are listed in Table 3.

Table 3 Amount of Effect of treatment before emergence mono- umbrella bulrush arrowhead active Be Choria plant 5 5 was partly Chicken 5 5 5 5 connection (at all) millet 5 5 5 5 No. 30 5 , 5 5 , 5 5 1 3 5 5 CJL " 5 5 30 5 5 5 5 5 - 2. % 3 ' 5 5 5 5 5 30   5 5 5 5 5 8th 3 5 5 5 5 5 30 5 5 5 5 5 9 3 CJL 5 5 5 5 30 5 5 5 5 5 11 3 5 5 5 5 5 30 5 5 5 5 5 13 3 5 5 5 5 5 30 5 5 5 5 5 17 3 Oil 5 5 5 5 30 5 5 5 5 5 18 3 5 5 5 5 5 30 5 5 5 5 5 19 3 5 5 5 5 5 30 5 5 5 5 5 21 3 5 5 5 5 5 30 5 5 5 5 5 22 3 5 5 5 5 5 30 5 5 5 5 5 26 3 5 5 5 5 5 30 5 5 5 5 5 31 3 5 5 5 5 5 30   5 5 5 5 5 32 3 5 5 5 5 5 30 5 5 5 5 5 33 3 5 5 5 5 5 30 5 5 5 5 5 34 3 5 5 5 5 5 30 5 5 cn 5 5 35 3 5 5 5 5 5 30 5 5 5 5 5 36 3 5 5 5 30 5 38 3 5

Amount of 3 Effect of treatment before emergence mono- umbrella bulrush -15-755 19 active Be Choria plant 5 was partly Chicken ul 5 5 connection (at all) millet ul 5 5 No. 30 5 ul 5 5 arrowhead 42 3 ul ul 5 ul 5 30 5 ul ul 5 ul 45 3 cn 5 5 5 ul 30 5 5 5 5 5 48 3 5 5 5 5 5 30 5 5 5 5 5 49 3 5 5 5 5 5 30 5 5 5 ul 5 53 3 5 5 5 5 5 30 ul 5 5 5 5 54 3 5 5 5 ul 5 30 5 5 5 5 5 55 3 5 ul 5 5 5 30 5 5 5 5 ul 56 3 5 5 5 ul 5 30 5 5 5 5 5 58 3 5 5 5 5 5 30 cn 5 5 5 5 61 3 5 5 5 5 5 30 5 ul 5 5 5 64 3 cn 5 5 5 5 30 5 ul 5 5 5 65 3 5 5 5 5 30 5 5 69 3 5 3 ul 4 4 3 5 Bezugsver 4 4 binding 3 3 A 3 3 B · 3

Reference compound A: Compound No. 1 = 1- (2,4-dichloro-5-isopropoxyphenyl) -4-difluoromethyl-3-methyl-A ² -1,2,4-triazolin-5-one as described in Japanese Patent Laid-Open Publication No. 57 No. 108079 (1982)

Reference compound B: Compound No. 7 = 1- (2,4-dichloro-5 - [[1-ethoxycarbonyl] -ethoxy] -phenyl-4-difluoromethyl-3-methyl-A ² -1,2,4-triazoline 5-one as described in Japanese Patent Laid-Open No. 57-181069 (1982)

Herbicidal Test Example 2

Control action for weeds in rice fields in the post-emergence stage:

Pots (ViooooAr) were filled with soil to simulate a paddy field and any of the harmful weeds were grown with the following leaf age. In addition, young seedlings of rice plants (culture: "Nihonbare") of the 2.5-leaf age were transplanted into the soil the day before treatment with each of the present herbicides After 21 days, the herbicidal activity and the degree of damage of the crops were compared by comparison Results with those of an untreated pot rated.

tested weed species

Leaf age of the weed

Millet Monochoria umbrella plant ^

Arrowhead water nut

2-3

1-2

2-3

1-2

The criterion for assessing the extent of damage to the culture of use is listed below:

H: strong (including dehydration)

M: medium

L: low

N: none

The criterion for evaluating the herbicidal effect corresponds to that of Test Example 1. The results are listed in the table.

Table 4

-16- 755 19

Amount of Effect of treatment after emergence mono- umbrella bulrush arrow water damage active Be Choria plant B herb nut the utility was partly Chicken 5 B S B B plants (at all) millet 5 B B 4 B connection 30 B 5 B B B B No. 3 B 5 B 5 B 4 rice 1 30 5 B B 5 B B L 3 5 B 5 B CJL 4 L 2 30 B B B B B s' L 3 4 B B B B B L 8th 30 B B B B 5 B L 3 4 5 B 5 5 4 L 9 30 B 5 B 5 5 B L 3 Ji. cn B cn 5 B L 11 30 5 B 5 B B CJL L 3 B B B B 4 4 L 13 30 B B B B B B L 3 B B B B 4 B L 17 30 B B 5 B 5 B L 3 B 5 5 B B 5 L 18 30 B B B 5 B 5 L 3 5 B B 5 B B L 19 30 5 B B B 5 6 L 3 5 B B B 5 5 L 21 30 B B cn B 5 B L 3 cn 5 B B B B L 22 30, B cn B B B CJL L 3 4 5 5 B 4 B L 26 30 5 5 5 B B 5 L 3 5 5 cn B B 5   L 31 30 5 5 5 B B 5 L 3 B B 5 B Ji. 4 L 32 30 ,in B B 5 B 5 L 3 cn B B 5 4 4 L 33 30 5 B 5 5 5 5 L 3 .5 B B B 5 5 , L 34 30 5 5 B B 5 5 L 3 5 5 5 B 4 4 L 35 30 B B 5 B cn 5 L 3 5 B 5 B 4 4 L 36 30 5 B 5 B B 5 L 3 5 B B 5 5 5 L 38 30 B B 5 5 B B L 3 B B B '5 B B L 42 30 B 5 B 4 B 5 L 3 5 B B 5 B 5 L 45 30 B B B 4 5 5 L 3 B B B 5 4 4 L 48 30 5 6 B B 5 B L 3 5 B B 5 4 B L 49 30 B B cn 4 B 5 L 3 B B B B 4 4 L 53 30 CJL 5 B 4 B B L 3 B B B 5 4 B L 54 , 30 B • B 5 5 B B L 3 B 5 B B 4 4 L 55 30 5 5 B B B B L 3 B B B 5 B B L 56 30 B B 5 5 B B L 3 B B 5 B B 5 L 58 30 B B B B B B L 3 5 · B B B 4 L 61 30 B L 3 B L 64 L L

Amount of Effect of treatment before emergence mono- umbrella bulrush arrow water  17-755 19 active Be Choria plant 5 herb nut damage was partly Chicken ul Oil Oil Oil ul the utility (at all) millet 5 ul Oil Oil Oil plants 30 5 ul ul 4 Oil OI connection 3 CJL Oil ul 4 4 No. 30 OI rice 65 3 ul 2 L 4 4 , 2 3 2 L 69 4 4 3 2 L 3 2 L Bezugsver 3 2 binding A L B L

The reference compounds A and B are the same as listed in Table 3.

Herbicidal Test Example 3

Control of weeds in higher fields at the pre-emergence stage:

10 χ 20 χ 5 cm (depth) polyethylene containers were filled with soil and sown with oats, barnyardgrass, large fingergrass, redroot foxtail, mugwort, gishi-gishi, umbrella sedgegrass, and seedlings Covered soil.

The soil was sprayed with each of the present herbicides formulated to form a given concentration of liquid. After 21 days, the herbicidal activity was evaluated by comparing the results with those of an untreated pot. The criterion for evaluating herbicidal activity is the same as in Test Example 1. The results are shown in Table 5.

Table 5 Amount of Effect of treatment before emergence Chicken great Rotwurzel- mugwort Gishi- Umbrella- cocklebur active Be millet crabgrass foxtail Oil gishi sedge Oil was partly ul 5 Oil Oil ul 5 Oil connection (at all) oats 4 5 Oil 5 5 Oil 5 No. 30 5 ul Oil Oil 5 5 Oil Oil 1 3 4 4 Oil 5 5 ul Oil Oil 30 Oil ul 5 Oil ul Oil 5 Oil 2 3 4 4 5 Oil 5 5 5 Oil 30 5 Oil Oil 5 Oil 5 5 5 8th 3 4 4 Oil Oil Oil 5 ul 5 30 ul 5 5 ul Oil Oil ul ul 9 3 4 4 ul ul 5 Oil Oil 5 30 5 Oil ul 5 Oil 5 5 Oil 11 3 4 4 ul 5 Oil Oil ul Oil 30 5 Oil 5 Oil Oil Oil Oil 5 13 3 4 · 4 Oil 5 Oil ul Oil 5 30 ul ul Oil Oil 5 ul 5 5 17 3 4 5 5 Oil Oil Oil Oil Oil 30 5 Oil Oil ul Oil Oil Oil Oil 18 3 4 Oil Oil 5 Oil Oil Oil Oil 30 ul ul Oil Oil Oil Oil Oil 5 19 3 4 ul 5 Oil ul Oil ul 5 30 5 Oil Oil Oil 5 ul ul 5 21 3 4 Oil Oil 5 Oil ul 5 ul 30 ul ul Oil ul ul 5 Oil Oil 22 3 4 Oil ul Oil ul 5 Oil 5 30 Oil Oil ul Oil Oil 5 5 ul 26 3 4 4 Oil 5 Oil ul Oil Oil 30 Oil ul ul 5 Oil • 5 Oil Oil 31 3 4 Oil ul ul Oil 5 Oil 5 30 Oil Oil 5 ul Oil Oil Oil 5 32 3 4 Oil ul Oil 5 5 Oil Oil 30 5 5 ul 5 Oil Oil Oil ul 33 3 4 5 ul 5 Oil 5 30 ul 34 3 4

Amount of effect in the treatment before emergence great Rotwurzel- mugwort Gishi- -18 _T 755 19 active Be crabgrass foxtail 5 gishi was partly Chicken 5 5 5 5 connection (at all) oats millet 5 5 5 5 Umbrella- No. 30 5 5 5 5 5 5 sedge cocklebur 35 3 5 5 5 5 5 5 5 5 30 5 5 CJT 5 Oil Oil 5 5 36 3 4 5 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 38 3 4 5 5 5 5 5 5 5 30 • 5 5 5 5 5 5 5 5 42 3 4 5 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 45 3 4 5 5 5 5 Oil 5 5 30 5 5 5 5 5 5 5 5 48 3 3 4 5 5 (Jl 5 5 5 30 5 5 5 5 5 5 5 5 49 3 4 5 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 53 3 4 4 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 54 3 4 5 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 55 3 3 4 5 5 5 5 5 5 30 5 5 5 5 5 5 OI 5 56 3 3 4 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 58 3 5 5 5 5 5 5 5 5 30 5 5 5 5 5 5 5 5 61 3 4 5 5 5 5 5 5 5 30 5 5th 5 5 5 * 5 5 5 64 3 4 5 5 5.- 5 5 5 5 30 5 5 5 5 5 5 5 5 65 - 3 4 4 5 5 5 5 5 30 5 5   5 5 69 3 4 5 4 5 5 3 5 4 3 5 5 Bezugsver 3 5 3 binding 3 2 3 A 3 1 2 4 1 B 4 2

Herbicidal Test Example 4

Control action of weeds in higher fields in the post-emergence stage: Polyethylene containers measuring 10χ20χ5 cm (depth) were filled with soil and the following weeds were sown and the seedlings were covered with soil. The weeds and soybeans were cultured until the following leaf stages and then treated with each of the present compounds at a predetermined dosage.

After 21 days, the herbicidal activity on the weeds and the extent of crop damage, soybeans, were evaluated by comparing the results with those of a non-treated pot.

Species of the test plant leaf stage oats 2 big fingergrass 2 Rotwurzel foxtail 1 mugwort 1 Gishi-gishi 2 Screen sedge 1 cocklebur 1 soybeans first Trifoliatstadium

The criteria for evaluating the herbicidal activity and the damage to the culture useful match those of the herbicidal Test Examples 1 and 2, respectively. The results are shown in Table 6.

-19- 755 19

Table 6 Amount of Effect of treatment after emergence great Rotwurzel- mugwort Gishi- Umbrella- cocklebur damage active Be crabgrass foxtail 5 gishi sedge 5 the crop was partly 5 5 5 5 5 5 (at all) oats 4 B B 5 5 5 connection 30 B 5 B B 5 5 5 Soybean No. 3 4 4 5 5 5 5 B L 1 30 B 5 5 5 B 5 5 L 3 4 4 5 5 5 5 5 L 2 30 5 5 5 B 5 5 5 L 3 4 4 5 B 5 5 5 L 8th 30 5 5 5 5 5 5 5   L 3 4 4 5 5 5 5 B L 9 30 5 B 5 5 B 5 5 L 3 4 B 5 5 B 5 5 L 11 30 5 5 5 5 B 5 B L 3 4 4 5 5 5 5 5 L 13 30 5 5 B B 5 5 5 L 3 3 5 5 5 5 · 5 5 L 17 30 5 5 5 5 5 5 5 L 3 4 B 5 5 5 5 5 L 18 30 5 B 5 5 5 5 5 L 3 4 B 5 5 5 5 5 L 19 30 5 5 5 5 5 5 5 L 3 4 B 5 5 5 cn 5 L 21 30 5 5 5 5 5 5 5 L 3 4 5 5 B 5 5 B L 22 30 5 5 5 B 5 5 B L 3 4 5 5 B 5 5 B L 26 30 5 5 5 B 5 5 B L 3 4 5 B B 5 5 B L 31 30 5 5 B · 5 5 B 5 L 3 4 4 5 5 B 5 5 L 32 30 5 5 5 5 B 5 5 L 3 4 4 5 5 B 5 5 L 33 30 5 5 5 5 B B 5 L 3 4 5 5 5 5 B 5 L 34 30 5 5 B φ 5 B 5 L "3 4 B 5 5 5 B 5 L 35 30 5 B 5 5 5 B 5 L 3 4 5 5 5 5 5 5 L 36 30 5 5 5 5 B B 5 L 3 4 5 5 5 B 5 5 L 38 30 5 B 5 B 5 B B L 3 4 B B B 5 B 5 L 42 .30 5 B B B 5 5 5 L 3 4 5 B B 5 5 5 L 45 30 5 5 B B 5 5 5 L 3 4 4 5 B 5 5 5 L 48 30 5 5 B B 5 B B L 3 4 4 5 B 5 B B L 49 30 B 5 5 B 5 B B L 3 4 5 5 B 5 δ 5 L 53 30 B 5 5 B 5 B 5 , L 3 4 5 5 B 5 5 5 L 54 30 5 B B B B 5 5 L 3 4 5 B B B 5 5 L 55 30 5 5 5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 56 30 5 5 5 5 5 5 5 L 3 4 B B B 5 B 5 L 58 30 5 5 B 5 5 5 5 L 3 4 4 5 5 5 L 61 30 5 L 3 4 L 64 L

Amount of Effect of treatment after emergence great Redroot. cn Gishi- Umbrella- cocklebur damage active Be crabgrass Foxtail mugwort CJL gishi sedge cn the crop was partly CJL 5 cn cn cn CJL connection (at all) oats 4 5 CJL cn 5 5 No. 30 5 cn 5 cn 5 cn Soybean 65 3 3 4 5 5 CJL L 30 5 3 L 69 3 3 3 2 L 3 4 2 3 2 L Bezugsver 3 4 3 3 binding 3 2 A 3 2 L B L

Example of a herbicidal composition - 1

A wettable powder composition was prepared by uniformly mixing and grinding the following

ingredients:

Compound No. 3 50 parts

Mixture of clay with "white carbon" (in which clay is the main constituent) 45 parts

Polyoxyethylene nonylphenyl ether 5 parts

Example of a herbicidal composition - 2

A granular composition was prepared by uniformly mixing and grinding the following ingredients, kneading the mixture with an appropriate amount of water, and granulating the kneaded mixture: Compound No. 25 5 parts

Mixture of bentonite with clay. 90 parts

Calcium lignosulfonate 5 parts

Example of a herbicidal composition - 3

An emulsifiable concentrate was prepared by uniformly mixing the following ingredients: Compound No. 50 50 parts

Xylene 40 parts

Mixture of polyoxyethylene nonylphenyl ether with calcium alkyl benzene sulphonate 10%

Claims (1)

-1- 755 19 Invention claim: 1. A herbicidal composition containing A ² -1,2,4-triazolin-5-one derivatives of the general formula (I) F O Cl -J / \\ - N O
ROCCHO