CS248742B2 - Herbicide agent - Google Patents

Abstract

DELTA <2>-1,2,4-Triazolin-5-one derivatives represented by the general formula, <IMAGE> (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 the substituents; an unsubstituted cycloalkyl group; a substituted-cycloalkyl group having halogen atoms as the 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; and unsubstituted-benzyl group; a substituted-benzyl group having 1 to 2 substituents selected from the group consisting 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; alpha -methylbenzyl group or a phenethyl group). The DELTA <2>,1 ,2,4-triazolin-5-one derivatives are useful as herbicides.

Description

This invention relates to ³ A -l, 2,4-tria.zolin-5-onicóýc.h derivatives IA herbicidal compositions which comprise the active ingredient as-these and ² -l, 2,4-triazcilin-54mi! 3 all derivatives.

The present invention relates to a herbicidal composition, characterized in that it contains, as active ingredient, A ² -1,2,4-triazoliin-5-oine derivative of the general formula I 'i.

ROCCHO

AND

_CH3 () alkenyl having 2-6 carbon atoms, alkynyl having 2 to 6 carbon atoms, alkoxyalkyl -group having 1 to 6 carbon atoms in aJkioixylu 1 -to 6 carbon atoms in the alkyl group alkylthioaiikylovou s- 1 (C 1 -C 6) alkylsulfinylalkyl, (C 1 -C 6) -alkyl, (C 1 -C 6) alkyl-C 1-6 -alkyl, (C 1 -C 6) alkoxyalkoxyalkylalkyl; -alkynyl-6-carbon atoms -alkyl, alkothiocarbonylalkyl-C1-C6alkoxy and C1-C6alkylalkyl, hydroxy-carbonylalkylamino-C1-C6-alkyl, benzyl-optionally substituted-1 to -2-substituents selected from the group consisting of -halogen, -alkyl of 1 to 6 carbon atoms, -adkoxy-of 1 to 6 carbon atoms, nitro, alkoxy C 1-6 -alkynyl having from 1 to 6 carbon atoms in alkoxy, hydroxycanibonyloxy and phenoxy, furthermore, α-methylbenzyl or phenethyllivia, together with suitable carriers.

A ² -l, 2,4-ti ^ i ^ a ^ io ^; IIn --- one derivatives of the general formula I according to this invention are novel compounds not -Which - -knows in literature.

v -ěmž

R is a hydrogen atom, an alkali metal atom, a monovalent ammonium salt, an alkyl group having 1 to 6 carbon atoms, optionally substituted by halogen atoms, a cycloalkyl group having (3-6C) optionally substituted halogen;

Certain compounds which are similar to above mentioned A2-l, 2,4-triazolin _L-5-one intermediate derivatives of formula I are described as active 'ingredient of the herbicidal compositions according · · Japanese Patent Offenlegungsschrift Nos. Sho 57-108 079 '(1982) and Sho 57-181 069 (1982).

The present inventors have discovered that compounds of the general formula. I have herbicidal activity and are therefore useful as agricultural herbicides.

The present invention ¹ further discovered that compounds of formula I exhibit surprisingly excellent herbicidal effect at relatively low doses and low fytotoxiciitami compared with the effect that the compounds previously described in the literature.

The object of the present invention. is to obtain new A2-1,2,4-triazolin-5-one derivatives.

It is another object of the present invention to provide herbicidal compositions comprising as active ingredient the A ² -1,2,4-thiriazoliin-5-one derivatives.

It is a further object of the present invention to provide a process for the preparation of A2-1,2,4-triazolin-5-one Ch 1 derivatives.

The compounds of formula (I) can be prepared, for example, by the following processes: according to Method A, according to Method B or according to Method C.

Method A

F ⁰ rur -> 1 JI chcC?

( ¹¹¹ ) _>

and? / - base ROCCHO CH ₃ CH- Cu) F 0 3 Cl 0 ~ (^ - _снг г -> ROCCHO ² \ ₃ OCH ₃ (l)

(wherein R is as defined above and Z ¹ is chlorine, bromine or iodine). ...........

Method B

HO (fv)

F

o II ROCCH.Z

(!)

ROCCHO

CH ₃ ^CH 3

(wherein R is as above and Z ² is halogen).

Method C i

(Vil) '- • p.

aJ

Cl o roCcho I

CH ₃ (wherein R is as mentioned above and X is a halo or hydroxyl group).

A ² -l, 2,4-triazolin-5-one derivative of the formula I can thus be produced according to method A, so that · the compound of 'the formula II is reacted with a compound of the formula · · III according to method B as A process according to claim 1, wherein the compound of formula IV is reacted with a compound of formula V and, according to Method C, that the compound of formula VII is reacted with a compound of formula VI, optionally in an inert solvent in the presence of a base. Compounds without basic compounds.

Any inert solvent which has no adverse effect on the reaction can be used as the inert solvent in these reactions. For example, aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, cyclohexane or the like, alcohols such as methanol, ethanol, propanol, ethylene glycol or the like, ketones may be used. such as laicetone, methylethyl ketone, cyclohexanoin or the like, lower aliphatic acid esters such as ethyl acetate or the like, ethers such as tetrahydrofunane, dioxane or the like, lower fatty acid amides such as dimethylformamide, dimethylacetamide or the like, water, dimethylsulfoxide or the like. The above solvents. can be used individually as such or as mixtures.

Furthermore, if an alcohol is used as the solvent in process C, preferably an alcohol corresponding to the compound of formula VI can be used.

When used, for example, in the above reactions, the basic compounds include inorganic basic compounds, for example, alkali metal hybrids such as sodium hybrid or similar hydrides, alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide or the like. similar hydroxides, carbon, and alkali metal such as sodium carbonate, potassium carbonate or similar carbonates, alkali metal hydrogen carbonate such as sodium bicarbonate, potassium hydrogen carbonate or the like. alkali metal alcoholates such as sodium methylate or the like alcoholates, and organic basic compounds such as pyridine, trimethylamine, tri and 1,8-diol; The compound is ethylamine, diethylaniline - [5, -4,0] -7-undecene or ny.

The reaction according to the invention can be carried out, for example, in the invention at a temperature ranging from 0 ° C to 150 ° C to a predetermined temperature.

The reactions of all steps are equimolar reactions. In practice, a slight excess of one reactant relative to the other reactant may be used.

The reaction time is any time ranging from 0.5 to 48 hours.

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

The compound of formula II, which is used as the starting compound in process A, can be synthesized by the following reaction steps:

(Vlil) ¹¹ ~

ROCCHO

CH ₃

R ~ A-- NC00R ^p = ²

---- CHa. (ΐχλ »heating mo basícka'slouPem.ua

C 1 - <(γ - NHC = NC 00 R ------------- ► ^CH 3 or α

ЯОССНО

F

(X) O A

-w NH

CH ₃

(In which R as mentioned above, R 1 and R ² are both the lower alkyl group and A is an oxygen atom or a sulfur atom).

Thus, the compound of formula (II) can be prepared by preparing a compound of formula (II). the compound of formula VIII is reacted with the compound of formula IX in an inert solvent with heating. The bbecine compound of formula X thus obtained is then treated under a ring-closing reaction condition with a basic compound, whereby the product is either isolated or not isolated from the reaction mixture.

The compound of formula IV, which is used as the starting compound in process B, can be synthesized according to the following reaction step:

HBr · --->

FO ct ²

RO CH?

(XI)

(wherein R 1 is as defined above). In the above reaction, hydroiodic acid or alkyl thiolate may be used instead of hydrobromic acid.

• Typical examples. The A2-1,2,4-triazolin-5-one derivatives of formula I are shown in Table 1 below.

Civ)

Table 1

compound number R physical properties. 1 H— n _D 24.5 1.5192 2 On- mp 186.1 ° C 3 TO- mp 119.2 ° C 4 ¹ +, NH ₄ - m.p. 92.7 ° C 5 ^ Ο - ^^ + ’Ν ^ - mp 157.3 ° C 6 (C ₂ H ₅ ) <+ »NH- oil substance. 7 (C ₄ H ₉ ) ₂ ⁽ + ^, nh ₂ - mp 126.5 ° C 8 CH3- n _D 2> 1.5142 9 C ₂ H5- n _D ¹⁰ 1.5112 10 C3H7— «D ^23.0 1.5051 11 ЙООД— iKd ²³ · ⁰ 1.5051 12 c ₄ h ₉ - Hd ²⁹ - ⁰ 1.5031 13 ÍSO- ^ Hg— nD29 1.5011 14 itenc.CHg— n _D 26 1.5009. 15 Dec C ₆ H _M - Hd27-5 1.4894 16 iso-CsHn— Dd ²⁶ 1.5002 17 C (> ^H 1.3— Dd28-5 1,4992 18 and CH 2 H 2 O 2 Dd26 · ⁵ .1.5204 19 Dec BrCHaCHa— Dd1 ⁹ - ⁵ 1.5291 20 May OlaCCHa— mp 106.5 ° C 21 FaCC ^ - Dd19 · ⁵ 1.4826 122 Н1НHзCH ₂ НHз— mp 87.7 ° C 23 BгCH2НH ₃ CH2— temperature. melting 83.8 '24 Н1НH ₂ (CHз) CH— mp 68.7 ° C 25 ClCHiCH ^ 1JCHa— mp 95.0 ° C 20 May . (ClCHa ^ H— Dd14- ⁵ 1.5091

(BirCH ₂ ) ₂ CH— (ВД ₂ СНClCHACHACHACHa— melting point 104.2 ° C in _D ¹⁹ · ⁵ 1.4573 melting point 95.3 ° C

Но ²⁶ 1.5130 n _D 27.5 1.5140 η ₀ 17 · 5 1.5174

33 CH2 = ^ C ^ H ^ CH2— Did ² 8'5 · 1.5156 34 CH ^CCHa α D 28 -5.5192 35 CH = CCH ₂ CH ₂ - Dd17- ⁵ 1.5209 36 CH3O _(CH2) 2- m m 1.5088 37 Dd26 1,5022 38 isK ^ '- C CH7O (CH 2) 2 - no.2 ⁶ '1.4989 39 Н ₄ HgO (НH ₂ ) ₂ - n _n 2fi 1.4878 40 ^ 900 ^^) 04 ^ 2— Dd27-5 1,5009 41 CH3SCH2— n _n 18 1.5279 42 (CH ₂ ) 2 - n _D 26-5 1.5306 43 N2H5S (N2H5) ₂ - Dd19 · ⁵ 1.5274 44 ÍSO-C3H7SCH2CH2— η _υ 19 · ⁵ 1.5233 45 iso-C ₄ H ₉ SCH ₂ CH - n-T- 1.5222 46 sek.C ₄ HgSCH2CHa— Dd19 · ⁵ 1.521 ' 47 target. ^ HgSC H2CH2— 0Dd22-5 1.5179 ' 48 НЩSН¾CH ₂ НH2.— Dd19 · ⁵ 1.52'9 49 C2H _S SCH ₂ CHiCH ₂ - 1Dd19'5 '1.5203 50 i »o-C3H7S ('CH9J3') n ,. ¹⁹ - 1.5204 ' 51 C ₄ H ₉ S (CH ₂ ) 3 - Dd ^K5 1.5216 52 iso-Н ₄ H9SНH2CH2ιCH2 .— m _c i4-5 1.520 ' 53 tettC; .Н4¾SНH2НH2CH2— W ^6-5 1.5172. 54 CHaSOCHaCHa— mp 104.5 55 CHaSO3r-CH2CH2— melting point 99.8 56 CHaOCHaCHsOCHjCHa— 1 ^ 26 1.5052 57 CH3 — O — CO — CH (CH31) - mp 108.1

. ° C ° C ° C is isothiocene

physical properties pool temperature 82.4 ° C melting point 117.5 ° C melting point 72.6 ° C melting point 73.0 ° C melting point 115.7 ° C melting point 80.0 ° C melting point 102.8 ° C melting point 89.4 ° C melting point 126.5 ° C melting point 135.3 ° C. No. ²⁶ 1.5588 melting point 163.5 ° No melting point 114.7 ° c melting point 96.5 ° C oilwelcome cloths.

oi®other substance

Table 2 below shows the NMR data of compounds in which it was stated in Table 1 that they were. oleaginous compounds.

T abu 1 and 2 NMR compound (CCl ₄ , TMS, ppm) No NMR compound (CCl ₄ TMS, ppm) No

1.15 (liritplet, 9H),

1.64 (doublet, 3H),

2.41 (siingleite, 3H),

2.19 (quartzite, 6H),

4.53 (quamtet, 1H),

7.03 (itie, 1H),

7.04 (doublet, 1H),

7.22 (doublet, 1H)

1.32 to 1.77 (multiplet, 6H),

2.30 (isinglet, 3H);

4.60 (quartet, 1H),

5.76 (fartartet, 1H),

6.86 (triplet, 1 H),

6.76 to 7.31 (mulitiipleite, 7H)

1.56 (doublet, 3H),

2.35 (siingleit ;, 3Ή),

2.84 (ifcripleit, 2H),

4.28 (triplet, 2 H),

3.59 (quartet, 1H),

6.91 (triplet, 1HJ,

6.85 to 7.32 (multi-year, 7H).

The invention is further illustrated by the following examples, but is not limited thereto.

Example 1

Prepn-avia, l- [4-chloro-2-trifluoromethylhydroxymethylene 5- [l- (etlh) oxykarbcóyl) elthioK-yl] phenyl | ^{-4-difluoromethyl-3-A-2} metihyil -l, 2,4 -triazoliin-5-enu (compound number 9)

Cl-

^CH 3

CH ₃

C

BrCl '! COOC ₂ H ₅ -------------- H _r C ₂ CH ₃ 0tfH0

A mixture of 13.27 g (0.045 mol) of the compound of formula IV, 9.06 g of 0.0498 mode) of N-benzonipiroipionic acid ethyl ester and

13.27 g (0.0962 imphodiol) of potassium carbonate was refluxed in 200 ml of acetone for three hours under stirring. After the reaction mixture was cooled to room temperature, insoluble materials were removed by filtration. The filtrate is concentrated by evaporation, the oily substance is dissolved in diethyl ether, the ether layer is washed with cold water, the diethyl ether solution is dried and the solvent is removed by evaporation. The oily substance, which is already pure in itself, is purified on a dry silica gel column. Yield: 14.7 g (83.1%). The refractive index n _O ^J9 1.5112.

Example 2

Preparation of 1- {4-chloro-2-trifluoro-5- [1- (hydroxycarbonyl) ethloxy] phenyl] -4-difluoromethyl-3- / methyl-N, N, 4'-triazololin-S-one (compound, number 1)

1.4 g (0.00356 mol) of 1- {4-chloro-2-fluoro-5- [1- (ethoxyicaribionyl) jettithioxyl] phenynyl-4-difluoromethyl-N, N, 4-triaolinolin-S-one Dissolve in 50 ml of ethanol. An aqueous solution of 1.2 g of hydroxide is then added to this solution. potassium (as a 50% solution). The whole 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 the desired product was extracted with ethyl acetate. The extract was washed with water and dried with sodium hydroxide and anhydrous magnesium sulfate. The solvent is then distilled off. This gave 1.1 g of an oil-like product. Refractive index Ud ²⁴ · ⁵ 1.5192. Yield 84%.

Example 3

Preparation of 2- [2-chloro-5- (4-difluoromethyl-3-methyl-5-oxio- ^{2 2} -1,2,4-sulfuric) O-linyl) -4-fluorophenoxypropionic acid sodium salt .acids (compound number 2)

0.5 g (0.00136 mole) of l- (4-chilor-2-fluoro-5- [1- (1 hydroxykarboiny) eithoxy] phenyl 1) -4-difluoinmietihyl-3-methy.lA -l ^2, 2,4-triazol-5-one is dissolved in 20 ml of tetrahydrofuran. To this solution was added 0.05 g (0.00125 mol of sodium hydride) and the whole was stirred for ten minutes at room temperature. After completion of the reaction, tetnalhyidirofuran was evaporated under reduced pressure and the residue was washed with hexane to give 0.50 g. 37 g of product, m.p. 186.1 ° C, yield: 76.4%.

Example 4

Preparation of 2- [2-chloro-5- (4-difluoromethyl-3-methyl-5-oxio-A ² -1,2,4-triazolin-1-yl) -4-fluorophenyloxy] propionic acid, tert-ammonium salt (Compound # 7)

ci - // Хм '' fi-a-ic, Cf, Μ / ^{> = / 1} ' ¹ '', ⁽ -> оссно сн ₃ , ~ сн,

V. *

.....,

0.5 g (0.00136 mole) of l- | 4 ch.lor-2-fluoro-5- [1- (hydroixyikaiťbonyl) -ethoxy] -phenyl-4-enylj difluoiřmerthyl-A-3 ² 2,4 L _t triazolin-5-ol is dissolved in 20 ml of benzene. To this solution is added 1 g (0.0139 mol) of dibutylliamine. Then the reaction is allowed to proceed while cooling constantly ledeim ^first The crystals formed in the reaction mixture are filtered, washed with benzene and dried. Thus, 0.51 g of the title compound is obtained. Melting point 126.5 ° C. Yield 79.4%.

Example 5

Preparation of l- {4-chl'oir-second-trifluoromethylhydroxymethylene 5- [1- (ipro | p.aírgyl • oxykisirbonyljetbioixylfeiniyll ^{dlfluioinmethyl-C-3-a-2} meithyl -l, 2,4-toilazo! Lin- 5-one ('Compound Pure 34')

A stirred solution of 20 ml of thionyl chloride containing 2.7 g of l- [4 <2-htor fluioir-5- [l- (hyidiroixyikairbioiniyl Jethoixy] phenyl} -4-luormetihyl ^{difluoro-3-methyl-2} -l 2 The 4-triazoilin-5-one was refluxed for two hours.

After completion of the reaction, excess thiomylchloiride is removed by distillation. It is obtained

2.8 g of 1- {4-chloro-2-fluoro-5- [1- (chlorocarbonyl) ethoxy] phenyl} -4-difluoromethyl-3-methylmethyl-A ² -l, 2,4-tri) azioilin-5-one (quantitative yield).

0.5 g of this compound (0.0013 mol) was then dissolved in 20 .mu.l of tetriahydrofuran. To this solution were added 0.2 g (0.00357 mol) of propargyl alcohol and 0.2 g (0.00198 mol) of triethylaimine. The whole reaction mixture was allowed to react wildly for 1 hour at room temperature. After completion of the reaction, the reaction mixture was poured into ice water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of 10% potassium carbonate and water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation.

The residue thus obtained is purified by dry column chromatography. 0.35 g of product is obtained. Refractive index По ²⁸ · ⁵ 1.5192. Product yield: 66.6%.

Example 6

Preparation of 1- {5- [1- (tert-butyl / xylcarbonyl) ethoxy] -4-chloro-2-fluoro-phenyl] -4-difluoromethyl-3-imethyl-η ² -1,2,2,4- triazolin-5-one (Compound No. 14).

C í ~

O

Cl CCHO ₃ CH ₃

q (CF 3 → COCCHO

AND

CH ₂

0.58 g (0.00151 mole) of l- (4-chloro-2-pentyl amino-5- [1- (chlorikairbonyil) ethoxy] phenyl} ^{-4-difluiormethyl-3-methyl-2} -l, 2,4-triazolin-5-one is added to a stirred solution of 0.25 g (0.00338 mol) of tert-butylalkiool, 0.14 g (60% suspension in oil, 0.0035 mol) of sodium hydride and 20 ml of tetoalohydrofuran .

The entire mixture was refluxed for six hours. After completion of the reaction, the reaction mixture was worked up in a similar manner to that described in Example 5. Yield: 0.13 g of the desired product. Refractive index Πη ²⁶ 1.5009. Yield: 18.8%.

Example 7

Preparation of 1- (4-Chloro-2-fluoro-5 - [(1- (methoxymethoxycarbonyl) ethoxycarbonyl] ethoxy) phenyl] -4-difluoromethyl-3-methyl-- ² -1,2,4-triazolo-5- onu (compound number 57)

HOCCHO ch.očchoccho • ³ I i ^CH 3 ^CH 3 .874.2-:

ΓΖ

181

Methyl solution. 0-5- g (0.00136 mol.) -1-chloro-IL-ZF-fluoro-5- [(- ethoxy.] Feny1j-4iidif1U'Onmet ^ ly1-34me, Thy1-A- ^'- -1; 2,4-triazolo-5-Oine 0.28g (0.00136 paint,

N, N &apos; -dicyclohexylcyclohexyldimide, 0.02 g (0.000164 &quot; mol) &lt; 4 &gt; 10. ml. diethyl ether. .react six. hours. at room temperature. completion of the reaction. se. insoluble materials are removed by filtration. Filter · .se. evaporates; · · The residue was purified by C.Hi ^^ - ^^^^ tx ^ o ^ ⁱ · rafrí to, dry sřlrkageiíi. 0.41 g of the title product is obtained. 1081 ° C. Yields 64.3 proe.

Example k-Faíd 8

EMpiraMa. 1- [4-Chloro-2-fluoro-5- (1- (ethoxycarbonyl) ethoxy] - [eta] &lt; 3 &gt; -1,3-dihydro-1H-pyrrole] -4- (4-chloro-2-carboxylic acid) ^; Rf ⁽ 5-thi ⁾ (Compound No. 9);

F ^ OCCHO ·

0.046 g (0.00134 mol). Sodium halide is suspended in ten. milliliters. Anhydrous N, N (N, N-N -) solution is added dropwise to this suspension, which is prepared by dissolving 0.4 g (0.00122 mol). - (4-chloro-2-). -fluor- [1-. (ethlooylcarbonyl) ethoxy) phenyl} -3-methyl-1,4-dihydro-1,2,3,4-dihydro-5'-oxo-5-ol. at room temperature; Ro drip-whole. the mixture is stirred. thirty. minutes. Then DO 'introduces a mixture of ¹ · Mo-nochlordiflúormietttan (C1CHF ₂₎ as - Gas: at 130th ° C for five. hours. Mon. completion of the reaction ^; The reaction mixture was cooled to a temperature. The reaction mixture was poured. into water. The resulting oily ¹ · '·· substance with *. extracts. The ethyl acetate / extract is washed with water. and dried. The solvent was distilled off. Gets. a substance which is. se ^; It is purified by dry chromatography. Yield 0.15. g of product. Index. quarry. Ud ¹⁹ = ^ - 1.5112. Yield; 3 ^ _Ύ 6 ^> 0-)

example. tb

BřlpKiaivaA l ^£ ^ {^^ l ^^ c ^ or ^ i ^ Z ^^ t ^'lu S * (Γ- (mettHiy-ylthio ^ -. ^ Y ^^ l ^ ιethoxítikar NLI ^^ 1)) eJrt , M¢ ok¢ttttttif ^ ^ ^ ^ t t t t t Dr Dr Dr Dr Dr Dr Dr Dr. methyl-3 * - (4-methyl-1'-1,2-diol-5-oine) (Compound No. 41)

Siměts 0.5 g (0.00137 mole) of l- [4-chloro-2-fluoro-5- [(1-hydroxy oxyikairboinyl) ethoxy] 4-feiпуР _г Ьй1ио) гте1Ьу1-3 ^{те11Ьу1-2-Л} -1 2,4-methylzoliin-5-ol, 1.76 g (0.00128 mol) of tert-butyl brioimide, 1.15 g (0.00137 mol) of sodium hydrogen carbonate) and 10 ml of dry dimethylsulfoxide are omitted. react with stirring at room temperature for 32 hours. After completion of the reaction, the reaction product was treated in a similar manner to that described in Example 8. Yield 0.4 g of the title product. Refractive index n _D ¹⁸ 1.5'279. Yield

68.7%.

A ² -l, 2,4-5- TriaizOilin / sulfonic derivatives of this invention are capable of regulating both annual and perennial weeds which grow in paddy fields :, upland fields, orchards and swamps, such as barnyardgrass (Echiiniochloa crus galii Beauv., an annual pleve-l of the genus Grlamineae, which grows in paddy fields and is very harmful), Moinochoirii (.Monochoria v-aginalis Presl, very harmful annual weed from Pointedeiriaicea, which is worn on paddy fields), chechoir (Cyperus diffoirimis L., harmful annual weed of Cyperaceiae growing on paddy fields], Eleocharis acicullaris Rómeir et Schuilteis, a typical harmful perennial weed of the genus Cypeiraceiae, which you carry on paddy fields and in waterways , arrowhead (Sagittiaria pygimiaea Miq.), a harmful perennial weed of the genus Alismaltaceae, which grows in rice p-olives, marshes and in the trenches), the scarp (Scirpus juncoides Roixb., var. rice fields, marshes and moats), deaf oats (Avenue fatua L., annual gramineae weed growing on plains, eels and upland fields), Arteimisii, (Artemísia priuicepis Pamip., perennial weed of Coostpoisitae, which n in cultivated and uncultivated fields), the dew (Digitaria aibscenduis Henr., a one-year-old weed of the genus Gramiineae, which is a typical harmful weed in the uplands and in orchards), Japanese sorrel (Rumex japonicus Houttuyn, perennial weed) Polygonaceae, which grows in the upland fields and around the roads, šáchoir (Cyperus isia L., a year-old weed of Cyperaiceaie, which grows in the upland fields and around: silnic), laskaiveic (Amiairanthiuis varldis L., a year-old weed of the genus Am-aranithaceae, growing ma upland fields, along roads and upland empty areas ¹⁾ and general řeipeň (Xanthium strumarium L., an annual weed of the genus Compoisi tae, a very harmful weed of soybeans).

A ² -l, _{2,4-triazol-1} zoilín 5 oiniové derivatives of general formula I exhibit excellent controlling effects on weeds in both pireemeirgeintoím and in postemergenitiním stage. They are therefore useful as herbicides for soil tillage before and after sowing (before and after sowing), for soil tillage in the growing season, for tillage before sowing (before planting), for tillage in useful growing above-ground crops such as soybeans, cotton, corn and the like. Furthermore, these derivatives are useful as herbicides which are applied at the initial or intermediate stage of rice cultivation and in paddy fields. In addition, they are useful as herbicides in the control of common weeds that grow, for example, in grooves between, paddy fields, agricultural roads, waterways, pastures, cemeteries, parks, roads, playgrounds, open areas around buildings, cultivated countries, railways and in the woods. The herbicidal treatment of these areas is carried out most efficiently and economically at the time the weeds germinate, although it is not necessary to carry out the treatment before weed germination.

The derivatives according to the invention are usually formulated for application as herbicides according to conventional methods for preparing agricultural compositions in forms suitable for use. That is, the derivatives of this invention are mixed with suitable carriers. If necessary, they are further mixed with the adjuvants in an appropriate ratio. By dissolving, dispersing, suspending, mechanically agitating, impregnating, adsorbing or adhering, a mixture is prepared in a suitable form, for example, as suspensions, emulsifiable concentrates, solutions, wettable powders, β-opyrose, granules or tablets.

Carriers used in agricultural compositions can be either solid or liquid. Examples of acceptable solid carriers may be wettable powders such as soybean meal, cereal meal, wood flour, bark flour, sawdust, powdered tobacco stems, powdered nut shells, bran, powdered cellulose and vegetable extract residues, fibrous materials such as are, for example, paper, paperboard and waste materials, synthetic polymers such as powdered synthetic resins, inorganic or mineral products such as clays (eg kaolin, bentionite and acid clays), tail products (eg talc and pyrophyll), silica products [e.g. diatomaceous earth, quartz sand, mica and charcoal (highly dispersed synthetic silica, sometimes called finely divided hydrated silica or hydrated silica; some of the commercially available products contain calcium silicate as the main constituent), activated carbon, spiked sulfur, pumice stone , calcined infused earth, ground bricks, fly ash, sand, calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloiride, and farmed manure. These solid carriers can be used either alone or in combination with each other. Acceptable liquid carriers can be solvents of the active ingredients or those which are non-solvent, but can disperse the active ingredients with adjuvants. Examples of such liquid carriers that can be used alone or in combination with one another are water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, and ethylene glycol), ketones [e.g. acetone, methyl ethyl ketoin, methyl isobuityl ketone, diisobutyl ketone, cyclohexanone and the like), ethers (eg diethyl ether, d-ioxain, whole-lions, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbons (eg gasoline and mineral oils), aromatic hydrocarbons (naphthalene); toluene, xylene, solvent naphtha and alkynyl naphthalene, halogenated hydrocarbons (eg dichloroethane, chlorinated benzenes, chloroform, and tetrachiormethlan), esters (eg ethyl acetate, dibutyl phthalate, diisopropyl phthalate and dioctyl phthalate), acid amides (eg dimeithytphorine) dieithylformaimide, dimethylacetamide), nitriles (eg aicetonitrile) and dimethylsulfoxide.

The adjuvants shown in the examples below are used according to individual needs. In some cases, combinations thereof are used. In other cases, the adjuvants are not used at all. Surfactants can be used to emulsify, disperse, dissolve, and / or wet the active ingredients, such as, for example, polyoxyethylene alkyl aryleithers, ipoilyl xoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resins, polyoxyethyleneworbitaine mioinooaurate, monooleate of hyalenesoirbitain, alkylarylsulphonates, condensation products ··lyphleylsulphonic acid, - ilgmm-ulphonates and sulphates of higher alcohols. Pro- stabilization dispergovatelniost, tackiness -and / or agglomeration of the active ingredients may be used například- následu.ící mlateriály: casein, gelatin ·, starch, alginic acid, methylicelulóza, kar ^l · bαxlmet'hll cellulose, gum arabic, -polyvinylalkoihol, -pine-pine-essential oil, rose bran essential oil, and bentonite; ligninsulfonates. To improve the liquid properties of the solid compositions, it is recommended to use waxes, stearates, ethoxyalkyl phosphates.

peptizing agent - for dispersible compositions it is recommended to use naphthalenesultonic acid condensation products - and - condensed phosphates. Antifoam agents such as silicone oil may also be added.

The content of active ingredients in the herbicidal composition depends on the method of application. Usually 0.5 to 20% by weight of the active ingredients are used for the preparation of powdered or granulated products. Usually 0.1 to 50% by weight of the active ingredients can be used for the preparation of emulsifiable concentrates or wettable solid powdered products.

For -ničení various weeds inhiibici or their _-ůstu: the »protection of crop plants against damage caused by these weeds ·, -se herbicidal compositions of this invention are used directly as such -v doses destroy weeds, in doses or- that inhibit weed -a growth. or, after appropriate dilution or suspension in water or in another suitable medium, are applied to the soil or. weed leaves in an area where weed germination or growth is undesirable. The amount of herbicidal composition to be used depends on factors such as, for example, the purpose of the crop, the type of weed, whether it is applied at the time of germination or at the time of vegetation of weeds and crops, weed germination, weather, conditions at the site of application, type of herbicidal composition, method of application, type of field to be treated, time of application, and other factors.

If the herbicidal composition according to the invention is a selective herbicide, then a dose of from 1 to 100 g per 1 hectare is suitable. However, when the herbicidal composition of the present invention is applied as a mixture of herbicides, the optimal dosage is usually lower. The herbicidal composition of the present invention may be used in lower amounts than the above, when used in combination with other types of herbicides. The herbicidal composition of the present invention is particularly valuable for pre-emergence processing for processing into. the onset of germination in the uplands or -for the control of the fields in the early or middle stages of vegetation in the paddy fields. In order to increase both the range of controllable weed species, as well as the time over which the application - an effective or - for dose reduction - the herbicidal composition of the invention can be used in combination with other herbicides. Such use of the herbicidal composition of the present invention is within the scope of this invention.

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

Herbicides - Phylloxyl-methanoic acid type:

for example 2,4-D:

e.g., (2,4-dichlorophenoxy) -acetic acid ethyl ester,

MCP: eg, ethyl (2-methyl-4-chlorophenoxy) acetic acid, sodium salt: (4-methyl-4-chlorophenoxy iodoic acid) and 2- (2-methyl-4-chlorophenoxy) iodoic acid allyl ester,

MCBP:

eg, (2- · methyl-4-chlorothenethoxy) butyric acid ethyl ester,

Die lofop-methyl:

for example, 2- [4- (2,4-dichloro-oxenoxy) -cyclohexyl] -propanoic acid dimethyl ester;

Diphenyl ether iherbicides:

for example nitrogen:

2,4-Dichlorophenyl-4-nitrile ^| rophenyl-e'ther,

СШ Cinnl triofein ;:

2; ^L Tric 4,6-hl-phenyl-4-niitroifenyl ELTHERM,

Gliloirmethoxynil:

2,4-di-chlorophenyl-3-n-thioxo-4-nitnophenyl ether,

Acifliiorfen:

5- (2-chloro-α, α-tert-trifluoro-β-talyllixyl) -2-nitrobeinizoleic acid; and its salts,

Filuazifóp-butyl:

(+) -2- (4 - [(57it: difluoromethyl / -2-pyridyl) oxy] phenoxyipropionic acid buitylester;

(Triaziin type herbicides:

for example, Simaizine: 2 ^ chliar-4'6-bis (eithy’iaimiino) -1,3,5-triia: zine, 2-chil (0ir-4; & -bis (eithhyHaniinio))

Promel tryne:

2-methylthio-4,6-bis (isopiriopyliamino) -1,3,5-triazine,

Stmetryne:

2-bitetyl-lithium * 4,6-bis (ethylamino) -1,3,5-triazine a

Méltribuziin:

4-amino-6-tert-butyl-3-methylthio-1,2,4,4-triazin-5 (H) -one;

type herbicides, KBnbamates:

for example, Moilinate:

5-methyl-hexyl-1H-azepine-1-carbothiothioic acid,

Swep:

N- (3,4-diichichirphirinyl) -quirinic acid methyl ester,

Chiliciroiproipha:

N- (3-Chloro-phthyl) -carbamic acid ispiropropyl ester a

Beintihllocairb:

S- (4-Chlorobenzyl) diethylthienylphosphoric acid;

toluidine-type herbicides:

for example, Tiriflurfaline: (α #, N-itirifluiar-2,6-dlinitrio-N, N-dlp) -propyl-p -toluide, and

Pendimethaline:

N - (1-ethyl-1-propyl) -2,6-dinitrile: 3,4-trifluoridine;

Acid amide-type herbicides: for example Pineplainil:

3.4- Dichlloirpiroipioinanilide

BúithehlOir:

N- (bulo: xy.methylthiyl) ШсНШ ^ 2; 6> Я1я * уу№с-tanilide;

AlacHlar · 2-chloro-lor-2,6-diethyl-N - '(ime®ax-ymetfayl) ^L aceteiniMd;

Metotechilbir-:

2-chloro-N- (2-ethyl-6-methylphenyl ·) -№- ^(2: * tbiOixy methyl-L-methyletHiyl Jee & tiaaniM 'and?

Preltilaicblioirh

2- ^{CHL-2,6-diethyl-l} · N- (2-pirqpioxyettiyl); aiceliainiiliid;

herbicides of other types:

for example Duirom :;

3- [3,4-diichlorophenyl) r / 1-diinethynylbiviina, Banti aaoia:

3- (5-piperidyl- (H) -2,1-, 3-benzothiiazin-4- (3H-10) -e-2,2-dioxido),

Pyrazolatě:

4- (2,4 ^x d .ichilioirbenizoyl.) '- LI3 dtoethy4pyra-on-l- &

- 5-γ-1-β-tolenenesulfine,

Pyinazexyfen: 1 ', 3'dllmeffiiyl-4- (2, -; 4 ^ |] | СИ.1йРНепи0у1.) - Promising ¹ cyloKypyraiZDlua

MY — 71:

4- (2,4-Difluoro-3-methylbenzoy-1) -radiylpyridine-S-yl-1β-toluenesulfonate.

The following examples illustrate Hwbielia's effects and hevbicidihi'pfrosfMedges'poiaie ^; this. invention. The present invention is not limited to the exemplary embodiment.

Example of the first hobbyist 'tests'

Regulatory account; : r.íosft na'lélélé to the »rice 'police · preemergouúní stage.

The crucibles (1 / 10,000) are completely supplemented to simulate rice-after. Db crucibles т & si eats the seeds of goat's corn; NBbnEWhertfe, šácihioiru and cvs ia> tubers arrowíffiiy · all are · harmful weeds'; that grow on: rice fields. The crucibles are retained in the preemerigenite network: In this stasis experiment, the compounds of the present invention (which are listed in Table 1) are formulated as liquids. concentration: Pb 21? The percent regulation of growth of the uterus of the elte in the untreated crucibles of the unloaded crucibles is compared with the Herbicide bill then determined according to the criteria shown in Table 2. '

Criteria, evaluation · ^; herbicidal activity degree herbicidal activity percentage weed growth control

Table 2

100 ALIGN!

Already 99 to 89 to 79 less than 70

The test results are summarized in Table 3.

Table 3

compound! number amount of active ingredient (g / 100 m ² ) effect in preelmergentmm processing hedgehog, corn leg, Monochoria šáchor skrpina arrow 1 30 5 5 5 5 5 3 5 5 5 5 5 2 30 5 5 5 5 5 3 5 5 5 5 5 8 30 5 5 5 5 5 3 5 5 5 5 5 9 30 5 5 5 5 5 3 5 5 5 5 5 11 30 5 5 5 5 5 3 5 5 5 5 5 13 30 5 5 5 5 5 3 5 5 5 5 5 18 30 5 5 5 5 5 3 5 5 5 5 5 17 30 5 5 5 5 5 3 5 5 5 5 5 19 Dec 30 5 5 5 5 5 3 5 5 5 5 5 21 30 5 5 5 5 5 3 5 5 5 5 5 - 22 30 5 5 5 5 5 3 5 5 5 5 5 26 30 5 5 5 5 5 3 5 5 5 5 5 31 30 5 5 5 5 5 3 5 5 5 5 5 32 30 5 5 5 5 5 3 5 5 5 5 5 33 30 5 5 5 5 5 3 5 5 5 '5 5 34 30 5 5 5 5 9 3 5 5 5 5 5 35 30 5 5 5 5 3 3 5 5 5 5 5 36 30 5 5 5 . 5 5 3 5 5 5 5 5 38 30 5 5 5 5 5 3 5 5 5 5 5 42 30 5 5 5 5 5 3 5 5 5 5 5 45 30 5 5 5 5 5 3 5 5 5 5 5 48 30 5 5 5 5 5 3 5 5 5 5 5 49 30 5 5 5 5 5 3 5 5 5 5 5

26

compound number amount of active ingredient (g / 100 m ² ) Effect in ipreimergent processing hedgehog corns the leg Monochoria šáchor skrpina arrow 53 30 5 5 5 5 5 3 5 5 5 5 5 54 30 5 5 5 5 5 3 5 5 5 5 5 55 30 5 5 5 5 5 3 5 5 5 5 5 56 30 5 5 5 5 5 3 5 5 5 5 5 58 30 5 5 5 5 5 3 5 5 5 5 5 61 30 5 5 5 5 5 3 5 5 5 5 5 641 30 5 5 5 5 5 3 5 5 5 5 5 -65 30 5 5 5 5 5 3 5 5 5 5 5 69 30 5 5 5 5 5 reference compound 3 5 5 5 5 5 AND 3 3 4 4 3 3 В 3 3 4 4 3 3

Reference compound A: compound no. 1 = 1- (2,4-dichloro-5-iiSopropoxyf einyl) -4-difl-fluoromethyl-3-and ^2-miefthyl -l, 2,4-trl.azoΙ, ϊΐη- 5-οιη, which is described in Japanese Patent Laid-open Publication No. 57-108,079 (1982).

Reference Compound B: Compound No. 7 = 1- {2,4-Dichloro-5 - [(1-ethoxycarbonyl) athoxyl] phenyl] -4-difluoromethyl-3-methyl- ^{2 2} -1,2,4-. triazoillin-5-one, which is described in Japanese Patent Laid-open Publication No. 57-181069 (1982).

Regulatory efficacy on weeds in rice fields in the positenae-genital stage.

The crucibles (1 / 10,000) will fill the soil, simulating rice fields. Harmful weeds are grown in pots with the number of leaves listed below. Next, young potatoe plants (cultivar: "Nihonbare") at a 2.5-leaf stage are transplanted into the pot in the pot one day prior to treatment with the respective herbicide, according to the invention. After 21 days, the efficacy and degree of crop damage are assessed by comparing the treated and untreated cups.

Example of a second herbicide test

A kind of weed hedgehog weed roots monochoria lichen crunch rosehip paspailcount, weed leaves.

to 3

- 2 to 3 3 to 2

The letters indicating the degree of crop damage shall have the following meaning:

H - major damage (including fading)

M - medium damage

L - slight damage

N - No damage

The criteria for evaluating herbicidal efficacy are the same as those used in the example of the first herhicidin test. The results are summarized in Table 4.

Table 4 shows the amount of efficacy in post-emergence treatment

n »and c. active ingredients (g / 100 m ² ) hedgehog corns the leg Мюпоchioria šáchotr skrpina. arrow paspal «Rice crop damage 1 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 2 30 5 5 5 5 5 5 L 3 5 5 5 5 5 4 L 8 30 5 5 5 5 5 5 L 3 4 5 5 5 5 4 L 9 30 5 5 5 5 5 5 L 3 4 5 5 5 5 5 L 11 30 5 5 5 5 5 5 L 3 4 5 5 5 5 4 L 13 30 5 5 5 5 5 5 L 5 5 5 5 5 5 5 L 17 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 18 30 5 5 5 5 5 5 L 3 5 5 5 5 4 5 L 19 Dec 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 21 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 22nd 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 26 30 5 5 5 5 5 5 L 3 4 5 5 5 5 5 L 31 30 5 5 5 5 5 5 L 3 5 5 5 5 4 5 L 32 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 33 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 34 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 35 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 36 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 38 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 42 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 45 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 48 30 5 5 5 5 5 5 L 3 5 5 5 4 5 5 L 49 30 5 5 5 5 5 5 L 3 5 5 5 4 4 4 L 53 30 5 5 5 5 5 5 L 3 with 5 5 5 4 5 L 54 30 5 5 5 5 5 5 L 3 5 5 5 4 4 4 L 55 30 5 5 5 5 5 5 L 3 5 5 5 4 4 5 L 56 30 5 5 5 5 5 5 L 3 5 5 5 5 4 4 L 58 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L

combined efficacy in post-emergence processing nina No effective hedgehog Monoshachoir hippopotamus paspal poecocomponent (g / corn chorion; pinning crop / 100 m ² ) rice

61 30 5 5 5 5 5 5 L 3 5 5 5 5 5  5 , L 64 30 5 5 5 5 5 : 5 L 3 5 5 5 5 5 : 4 . L 65 30 5 5 5 5 5 5 L 3 5 5 5 5 5 5 L 69 30 5 5 5 5 5 '5 L 3 5 5 5 4 4 í 4 L referenč- merging nina AND 3 2 4 4 2 3 2 L В : з 2 4 4 2 3 2 L

Reference compounds are the same as above; Table 3.

Example of a third herbicidin test

Regulatory efficacy on: weeds in pre-emergence stage in upland fields.

Polyethylene tubs with dimensions of 10 x 20 x 5 cm (depth) are filled with soil in which seeds of oats, hedgehogs of corn, bloody dew, amaranth, Artemisia, sorrel, cyperus iriia L. and beetroot are planted. . The seeds are covered with earth. The earth is treated by spraying with the herbicide liquid according to the invention at a given concentration. After 21 days, the herbicidin activity is evaluated by comparing the treated and unprocessed plants; The herbicidal activity criteria are identical to the criteria; which was used in the example of the first herbicide test. The results are summarized in Table 5.

Table 5

Compound Й. amount of active ingredient (g / 100 ta: ² ) otves 1 30 5 3 4 2 30 5 3 4 8 30 5 3 4 9 30 5 3 4 11 30 5 3 4 13 30 5 3 4 17 30 5 3 4 18 30 5 3 4 19 Dec 30 5 3 4 21 30 5 3 4 22nd 30 5 3 4 26 30 5 3 4 31 30 5 3 4 32 30 5 3 4

efficiency in pre-emergence processing

corns foot roisič- lais- Artemlsla sorrel · jap. šá. chorus re. stump ka t : avec 5 5 5 5 5 5 '· 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 ' 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 > 5 4 5 5 5 5 5 5 5 5 5 5 5 5 :> 5 4 5 5 5 5 5 5 5 5 5 5 5 5 '· 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 :: 5 5 5 5 5 5 5 5 5 5 5 5 5 5 . 5 5 5 5 5 5 ’ 5 5 5 5 5 5 5 5 : i 5 5 5 • 5 5 5 5 5 5 5 5 • 5 5 5 H 5 5 5 5 5 5 5 5 5 5 • 5 5 5 5 5 5 5 5 : 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

Compound No · amount of active ingredient (g / 100 m2) efficiency in pre-emergence processing •Oat corns foot rosička l-askaivec Artemisla Sorrel jap. šáchor re- stump 33 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 34 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 35 30 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 36 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 38 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 42 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 45 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 48 30 5 5 5 5 5 5 5 5 3 3 4 5 5 5 5 5 5 49 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 53 30 5 5 5 5 5 5 5 5 3 4 4 5 5 5 5 5 5 54 30 ' 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 5 5 55 30 5 5 5 5 5 5 5 5 3 3 4 5 5 5 5 5 5 56 30 5 5 5 5 5 5 5 5 3 3 4 5 5 5 5 5 5 58 30 5 5 5 5 5 5 ' 5 5 3 5 5 5 5 5 5 5 5 61 30 5 5 5 5 5 5 ' '5 51 3 4 5 5 5 5 5 ' 5 5 64 30 5 5 5 5 5 5 5 5 3 4 5 5 5 5 5 (5 5 65 30 5 5 5 5 5 5 ' 5 5 ' 3 4 4 5 5 5 5 5 5 * 69 30 5 5 5 5 5 5 5 5 ' 3 4 5 5 5 5 5 5 5 ' reference compound AND 3 2 3 3 5 4 3 4 1 (B) 3 1 2 3 5 4 3 4 2

Example - Fourth - Herbicide - Test species of plant number of leaves

Regulatory efficacy -on weeds in -postemeirento-stadium in the upland fields.

Polyethylene tubs 10 xx 20 x 5 cm. (depth ¹ ) is filled with soil into which the following seeds are planted together with soybean seeds. The seeds are covered with soil. The weeds and soybeans are cultured into the foliage number below. They are then treated with the active compounds according to the invention in given doses. After 21 days, the herbicidal activity on weeds and the degree of soybean damage was evaluated by comparing the treated and unprocessed plants:

oat Woolly Antemiisia sorrel Japanese sauerkraut beetroot bloody soy bldb 'first triplet

The criteria for evaluating herbicidal efficacy and crop damage are in accordance with the criteria used in the first and second herbicidal test examples. The results are summarized in Table 6.

2- 4 8 7.4 2

T and b are 1 k and 6 compound. Effective amount of paste processing

& active-ingredients oats ro-las-art-sash-poo. - (g / 100 m2) sachet casserole mix lid lids nursery jap · crops soybean

1 30 5 5 i5 5 '5 5 5 L 3 4 4 5 5 5 5 5 L 2 30 5 5 5 5 5 5 5 L 3 4 4 5 5 5 5 5 L 8 30 5 5 5 5 · 5 5 5 L 3 4 4 5 5 5 5 5 L 9 30 5 5 5 5 5 5. 5 L 3 4 4 5 5 5 5 5 L 11 30 5 5 5 5 ’ 5 5 5 L 3 4 4 5 5 5 5 5 L 13 30 5 5 5 5 5 5 5 L 3 4 5 5 : 5! 5 5 5 L 17 30 5 5 5 5 5 5 5 L 3 3 4 5  5: 5 5 5 L 18 30 5 5 5 5. 5 5 5 L 3 4 5 5 5 5 5 5 L 19 Dec 30 5 5 '5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 21 30 5 5 ' 5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 22nd 30 / 5 5 5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 26 30 5 5 5 5 5 5 5 L 3 4 5 5 5. 5 5 5 L 31 30 5 5 5 5 5 5 5 L 3 4 5 5 . 5 5 5 5 L 32 30 5 5 '5 5. '5 5. 5 L 3 4 5 5 5 5 5 5 L 33 30 5 5 5 5 5 5 5 L 3 4 4 5 · 5 5 5 5 L 34 30 5 5 5 5 5 5. 5 L 3 4 4 . 5 5 5 5 5 L 35 30 -5 5 5 5 5 5 ? - 5 i. L 3 4 5 5 5 5 5 ·. 5 . . L 36 30 5 5 5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 38 30 '5 5 5 5 5 5 5 L 3 4 5 5 5 5 5 5 L 42 '- 30 '5 5 5 5 > · 5 5 5  L 3 4 5 5 5 5 5 5 L 45 30 5 : 5 5 5 5 5 .5 L 3 4 5 5 • - 5 Ί 5  5 5 i - L 48 30 '5 - 5 5 5 '5 5 5 L 3 4 5 5 5 '5 5 5 L 49 30 6 : - 5 5 χ 5 5  5 . 5 L 3 4 4 5 5 5 • 5 5 .. L 53 30 5 5 5  5 5 5 5 L 3 i 4 4 5 5 5 5 5 L 54 30 5 5 5 5 5  5 > 5 L 3 4 5 · 5 5  5 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 5 5 5  · 5  5 . 5 L 58 30 5 5 5 5 5 5 5 L 3 4 5 5 5 5 5 5 AND·

compound. The amount of efficiency of post processing:

C. active ingredients (g / 100 '.on ² ) avos rosička kindness Artemisia Sorrel jap. šáchoir beet damage to the soybean crop; 61 30 5 5 15 Dec 5 5 5 5 L 3 4 5 5 5 5 5 5 L 64 30 5 5 5 5 5 5 5 L 3 4 4 5 5 5 5 5 L 65 30 5 5 5 5 5 5 5 L 3 3 4 5 5 5 5 5 L 69 30 5 & 5 5 5 5 5 L reference compound 3 3 4 5 5 5 5 5 L AND 3 2 3 4 3 2 3 2 L (B) 3 2 3 4 3 3 3 2 L

An example of a first pharmaceutical composition

The wettable powder composition is prepared by uniformly mixing and grinding the following ingredients:

compound number 3 50 parts clay-white clay mixture in which clay is the main component 45 parts noinylphenyleither ipolyoxyethylline 5 parts

Example of a second herbicidal composition

The granular composition is prepared by uniform mixing, grinding, wetting with an appropriate amount of water and granulating the mixture obtained from the following ingredients:

compound number '25 mixture of bontonite with clay calcium ligninsulfonate parts parts parts.

An example of a third herbicidal composition

An emulsifiable concentrate is prepared by uniformly mixing the following ingredients:

compound pure 50 50 parts xylene 40 parts mixture of nonylphonylothier, polyoxyethylene with calcium alkylbenzisulphioinate 10 parts.

Claims (3)

OBJECT OF THE INVENTION 1. A herbicidal composition characterized in that it contains as active ingredient Δ ² + ^ -l ^ triazolln -ionavý compound 'of general formula I ^CH 3 (optionally substituted D' atoms. 'Halogen, an alkenyl "having 2 to 6 carbon atoms, (2-6C) alkyl, (1-6C) alkoxyalkyl, (1-6C) alkoxyalkyl (1-6C) alkyl, (1-6C) alkylthioalkyl; alkyl carbon atoms, C1-6 alkylthioalkynyl alkyl, C1-6 alkylsuffianylalkyl, alkoxyalkoxyalkyl, C1-6 alkoxy and 1-6 carbon atoms in alkyl, alkoxycarbonylalkyl having 1 to 6 carbon atoms in the alkoxy and 1 to 6 carbon atoms in the alkyl, a hydroxycarbonylalkyl having 1 to 6 carbon atoms in the alkyl, a bonzyl group optionally substituted with 1 to 2 substituents which they are selected from the group consisting of halogen, alkyl of 1 to 6 carbon atoms, alkoxy groups of 1 to 6 carbon atoms, nitro, alkoxycarbonyl of 1 to 6 carbon atoms in alkoxy, hydroxycarbonyl and phanoxy groups, furthermore o-methylbenzyl; or fono in which R is hydrogen, alkali, quaternary ammonium, alkyl. C 1 -C 6 optionally substituted by halo, C 3 -C 6 cycloalkyl, TiH 2. together with suitable carriers. 2. A herbicidal composition as claimed in claim 1, characterized in that it contains as active ingredient A ² -1,2,4-triazole. A volatile derivative of the formula I wherein R represents an alkyl group having 1 to 3 carbon atoms. 3. A herbicidal composition as claimed in claim 1, wherein the active ingredient is an A2-1,2,4.-traaisyl-5-one deiriiivat of the general formula I, in which R represents a hydrogen atom, an alkali metal atom, or quaternary. ammonium salt, (C 1 -C 6) alkyl, (C 1 -C 6) alkyl, optionally substituted with halogen atoms, (C 3 -C 6) cycloalkyl, optionally substituted with ¹ halogen atoms, (C 2 -C 6) alkenyl C 2 -C 6 alkynyl, C 1 -C 6 alkoxy alkyl in alkoxy. and (C 1 -C 6) alkyl, (C 1 -C 6) alkyl, (C 1 -C 6) alkyl, (C 1 -C 6) alkyl, (C 1 -C 6) alkyl (C 1 -C 6) alkyl and _L lkoxyaUOюxaaUkylQvou group having 1 to 6 ato | we atoms in the alkoxy and. (1-6C) alkyl, (1-6C) alkoxy, (1-6C) alkoxy and (1-6C) alkyl, (1-6C) hydroxycarbonylalkyl, benzyl, optionally substituted with 1-2) substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, C 1 -C 6 alkoxycarbonyl, hydroxycarbonyl, and Tenoxy , furthermore, represents an α-methylbenzyl group and a phenethyl group.