CS219947B2 - Herbicide means - Google Patents

Abstract

A herbicidal composition is provided which is characterized by the combination use as active ingredients of a thiocarbamate derivative of formula I: <IMAGE> wherein one of X and Y is a hydrogen and the other is a chlorine and 4- amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one of the formula: <IMAGE> Also provided is a process of inhibiting the growth of unwanted plants by applying the herbicidal composition to the plants or to the soil where the plants are grown.

Description

The invention relates to a herbicidal composition, in particular a herbicidal composition comprising: in combination a thiocarbamate derivative and a triazine derivative as an active ingredient, as well as a method of administering the composition.

In recent years, was developed and applied in practice, many herbicidal compositions what ^made 'm about ^El for us ^to ede ^l s ^{p p p} oru ručrn Race in agricultural work. However, since there have been various problems with the efficacy and safety of herbicidal chemicals in their practical use, there is still a need for new improved herbicides, in particular high-safety herbicides which do not have harmful effects on crop plants, have a significant effect on harmful weeds at low application rates and do not cause eye ^{in the} environment.

Gčetom in ^y n and ^l is the cut-poskyrno herbicidal composition and a method by which ^"would · ^s at ^YH ovoval above requirements AVK ^{d of} m.

The invention firstly provides a herbicidal composition Ahuja · o ^ v · ^d tombinad Eriva ^sulfate thtokarbam CS ^ ^b ecného formula I

one of symbols X and Y represents hydrogen and the other is a chlorine atom, in combination with 4-amino-3-meth ^{yl-6-phen y} l, 2,4-triazin-5 (4H) -one of the formula II

· as an active ingredient in a weight ratio of 1 ·: 0.05 to 1: 10, wherein the active ingredients are contained in a weight · koncentoarn ranging ⁱ °, 5-8 ° ° / o.

^{'Lou OF} <n ^{y in} general formula ^I, ktorýc ^H is used in the composition according vyjsou Zn ^and m ^y j and ^k of úmnné ^h er ^b ICID ^y for controlling a series of annual grass weeds such as barnyard grass (Echinochloa spp. j, Rosi and ^RC (Digrtaria sppj RER · (Setaria sp ^p .ja annual bluegrass (Poa annua spp.ja nutsedge ^(Cyp crus spp.j ^P ro ^ Employment of ^{kh b} u ern ^p leve ^l ev crops, such as roses, Uric ^{к to,} soybean ^b of ^b, and ^R e ^and Cu and ^{to the} ROV.

^{Lou No. 11} The compounds of formulas TCD is known as a herbicide for killing. of various annual broadleaf weeds such as cotton (Polygons spp.j, white goosefoot (Chenopodium album), white amaranth (Amaranthus albus) and chickweed (Stellaria media), when applied during their growing season with such high safety that it practically does not harm some crop plants, especially sugar beet.

However, none of the compounds of formula I · II and is not always effective as perfectly seteMvrn erbicidat ^h, is used - i · v If the quantity or amount ^ at low concentration for controlling chaff rostoumch to Tenec ^h SOLUTIONS ^py diabetes. Thus, the compounds of formula (I) have excellent herbicidal activity against grass weeds in pre-emergence application without having a detrimental effect on sugar beet but are not sufficient in low amounts or at low concentration to completely destroy broadleaf weeds and grass weeds in post-emergence application . By contrast, the compound of formula II · excellent herbicidal activity against weeds by širokollstým posteemergentní application selekUvnou high, i.e. not with ^{the Pooh is running} practitioners · ^ on sugar beet, but is ineffective towards širokollstým weeds and grass weeds · Pre-emergent.

The compound of formula (II) also has insufficient fungicidal abundance in the patches where it is raining soon after application, or against old broadleaf weeds.

A combination of both · mentioned compounds · formula ^{U I} and ^II according to ^y n and ^l of cut allows destroy pre-emergence broadleaf weeds postemergence ^g-covalent toavní ^p Tevel ^y and old siro ^to ohsto ^pl evel ^y, which can not possible ^from non use · ka ^Here z · of said compounds individually.

· The composition of the invention has significant tedy- · _ herbicidal activity against a wide variety of unwanted weeds including annual toavrnch Ievel ^{of p} and broadleaf ^ ^pl eve ^profiles throughout the growth period by pre- and post-emergence application in a small amount or · at low concentration. Composition according to v ^ átezu after aplikam straight ^from rainproof thus provides stable long herMmdm · U ^or not ^{to. You} Soka stabihta for cutting, the terms high efficiency · especially against old broad-leaved weeds and immediate artfully ^ sm ^ ^p ccording to ^y n and ^l cut are probably due to the ease with which component = U ^No. Enma formula П is ateoréována the body weed plants for with a compound of formula (I).

The invention indeed based on the discovery that kombinam compounds of formulas ^of I and II not only odstrarn not getting ^alkyl and ^p Ukace ka ^here from toc ^h the composites jednotíivě, j and ^k bytes presented above but the combination also provides an unexpectedly high synergistic effect by The combination according to the invention can simultaneously control both grass weeds and broadleaf weeds growing on fields sown with sugar beet, and the combination according to the invention is characterized by a high herbicidal activity throughout the growth period of the weeds during pre-emergence and post-emergence application.

It was also zjtétěn-on that prostaedek: ^p ccording to the invention is effectively applicable not only for controlling weeds in beet fields, but also in fields where grows spinach, barley, wheat and corn.

The invention also provides a method of inhibiting growth of weeds in fields of beets, spinach, barley, wheat and maize, which is characterized in that the fields in the pre-emergence of the crops, or after treated with a composition containing as an active ingredient The compounds of formulas ^{Y U} i and ^ 1 in an amount sufficient to prevent growth of weeds but insufficient to heavy damage crops. For pre-emergence application, the composition according to the invention can be treated with soil in which the seed of the crop to be sown has been sown, preferably by spraying. In post-emergence application, the composition of the invention is usually applied to the stems and leaves of plants, preferably by spraying. '

Examples of compounds of formula I used in the herbicidal composition of the invention are:

Compound A:

s- (p-chlorobenzyl) -N, N-diethylthiocarbamate o

~ \ П LI /

Compound B:

s- (o-chlorobenzyl) -Ν, Ν-diethylthiocarbamate (O> -ch ₂ sc-n

V— / Xf H

The synergistic effect of the herbicidal medium ^to at after ^dL e vynátezu is obzvtasť pronounced at certain specific ratio of the compound of formula I to the compound of formula II, the weight ratio ^of ro ^b ou ^I c ^ht merge ^ used in ^p COMPOSITIONS of the present invention can vary within relatively wide limits. It is generally desirable ^p ou l ^{y 0} 0S to 10 ^hours motnostních days, preferably 0.125 to 4 parts by weight, and both ^of the ^LA ST ^{E 0,} 25-2 hmotaostní portion ^Y of ^the compound of formula II (hereinafter referred to as Compound C to 1 part by weight of the compound of formula I.

The herbicidal mixture according to the invention may be prepared in any form compositions ob sahupmto ^tepee ck ^{y 0,} 5 to ^80% by weight of active ingredients, such as PR ^and smáčitetaé § ^alkyl or grains · ^emu ^ dusts, granules, flowable suspensions and the like.

^p s ^p rost výrbbě herbiculrnbo ^of composition ^{of the} agent ccording to the invention, the active ingredient is mixed with a diluent or carrier ·. Suitable solid diluents or carriers include, for example, talc, bentonite, clay, kaolin, diatomaceous earth, silica, vermiculite, slaked lime, silica sand, calcium carbonate, dolomite, powdered magnesium oxide, Fuller clay, ammonium sulfate, and urea.

Suitable liquid diluents or carriers include, for example, alcohols, dioxane, acetone, cyclohexane, methylnaphthalene, dimethylformamide, and acetonitrile.

Surfactants which can be used as emulsifying, dispersing or suoping agents in the herbicidal composition of the invention may be of the cationic, anionic or non-ionic type.

^Vh withdrawn čintala kattontového ^type include for example kvartér.ní ammonium compounds such as cetyltrimethyl ammonium bromide, for example. Suitable anionic-type agents include, for example, soaps, salts of aliphatic monoesters. ^{ky y} Selin ^sulfuric Jato as sodium lauryl sulfate, and воИ sulphonated aromatic compounds, such as; is dodecylbenzenesulfonate, sodium, calcium, or ammonium lignosulfonate and butylnaphthalenesulfonate. Suitable agents of the non-ionic type include condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkyl phenols such as octyl phenol, nonyl phenol and octyl ^to R ESOL ^part No. ^as esters derived · mastnýcli 'acids dtauhým chain anh ^yd r ^Ids hexitol such as sorbitan monolaurate ·, and condensation products of said partial esters with ethylene oxide ·, · such as polyoxyethylene sorbitan monolaurate.

In a composition according to the invention it is also possible to use various other PNAS ^kt erých ^{the YKL} bv e použwá pH formulating herbicidal compositions such as karhoxymethylcelulóza or acacia.

The application rate of the active ingredients of the compositions according to the invention depends on weather conditions, soil conditions, application form, season of the year, method of application, crop species, weed species and weed growth stage and is usually in the range 0.5 to 30 kilograms. preferably from 2 to 12 kg and in particular from 5 to 8 kg / ha, for soil or leaf treatment. The composition according to the invention is usually applied in a concentration of from 500 to 30,000 ppm, preferably from 2000 to 20,000 ppm and in particular from 5,000 to 10,000 ppm of active ingredients. In case of application of a herbicidal composition by aerial spraying or dusting · concentration of active ingredients is usually in the range ^I w 00 ⁰ to ^{75 000} parts ^per million.

For example, 0.5 to 1.5 kg of active ingredients are sprayed at a dosage of 20 to 50 liters / ha.

When applying the 'herticídní ^{p p} rostredek ccording to the invention is applied in undiluted form after ně'o dil ^e n ^{s p} limbs water to no ^{b y} the stems and leaves of plants, as discussed above. The composition herbicklnímu ^p ccording ^{characterized} judgment can ^also be ipřidat other herbicides ^to substantially enhance its herbicidal activity. .

In ez ^y n and ^l is in a given ^{width b} m ^b hže a ^clearly ns ^p ecifickými embodiments the formulations, to which however the invention is not limited. Thus, the weight ratios of the components used as well as the types of carriers can be varied. Unless otherwise indicated, all parts, percentages, ratios, etc. are by weight.

a) Emulsifiable concentrate 80% ·, preferably between 1 ° ^{and 70%,} and especially ^E in 15 to 3 ^0%. actives ^kd e ^p M ^e s for the compound ^of I and II is 1: ^'(0, 5 to 10) is dissolved in ⁵ to ⁹⁰ ° / o, preferably 3 ^{0-6 0} / o of the liquid noslče ^{to some} man ^hydride and p ^{is from 1 to 40} the advantage of θΑ ^d ou ⁵ and ^{20% of} emulsifying agent ačmho ^.

b) Wettable powder

Minced, důtíadným mixing 5 and ⁸⁰ θΑ with výtodou ²⁰ to ⁵⁰ ° / o for & nných components which ponmr solubilizing amount of compounds of formulas ^of I and II is 1 ': ^(0.05 to 10], ¹ to ²⁰ ° / o', p preferably 5-1 ⁰ / o ^{p h} o ^of ovrc aktivrnho agent and 5 to ^85%, preferably between ⁴⁰ and ^70% tohého carriers with ^{Ravi, PR} and ^P ^ i ^ s ^ t itel.ný ^PRA ek.

c) Dusts ^{0.5 and} 10%, with the above ^H ou ^{d 1} '5% of active ingredients which ^p om ^e' r ^LeVeLs Community sloušnrn formula I and Π is ^{1: (0,} 05 and ^of W) , pulverized and well Romis ^{p s 90} 9 to ^99.5 °, preferably 95 to 99% of the ^HEH wear.

(d) Granules

0.5 to 40, preferably 2 to 10% of ingredients of účinnýc ^h MCHZ ^p Omer amount ^of compounds of formulas ^I and ^II is ^{1: (0.05} to dimension it & thoroughly Romis ^{e p s} to 6 ⁰ to ^99.5 why ^ preferably ^90-98 θΑ more rigid support and the obtained mixture was kneaded with addition of ^{water, n} is Acez granuhije and dried ^compounding MZ give the desired granules.

Example 1 - Enumerable powder

A wettable powder is prepared by homogeneously mixing and pulverizing 30 parts of Compound A, 20 parts of Compound C, 2 parts alk ^y l ^b enzensul ^sulfonate, sodium ^p olyvl dtíů 3 · alcohol, 20 parts of white carbon and 25 parts of 'fine powdered clay.

Example 2

Wettable powder

Smáčtíelný pnpraví homogeneous powder ^P romíseníin and grinding ⁴ parts of Compound ^y 0 B ²⁰ days ^No enyne compounds ^y C, 2 parts ^b enzensutíon alkyl ^sulfate with sodium ^hours of ³ parts. ^p ol ^{y l} alkholu guilt, 20 parts of white carbon and ¹⁵ days -rozsivkové soil.

Example 3

Wettable powder

A wettable powder is prepared by homogeneously mixing and grinding 30 parts of Compound A, ^{10 'di} profiles of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 35 parts of fine powdered clay.

He attaches

Wettable powder

A wettable powder is prepared by homogeneously mixing and grinding 40 parts of Compound B, 10 parts of Compound C, 2 parts ^kylb al enzensuli ^sulfonate, sodium 3 · polyvl portion ^of alcohol, 20 parts of white carbon and 25 parts of fine powdered clay.

Example 1 a d 5

Wettable powder

A wettable powder is prepared by homogeneously mixing and grinding 30 parts of compound ^No. enyne ^y C, ^{2 parts} of sodium sulfonates alk _^y> 3 parts of ^{the poly} vin ^yl and ^{l l} in ^{whom, 20} days sličníku ^alkyl silicate and ¹⁵ days rozswkové soil.

Example 6

Wettable powder

Wettable powder is prepared by homogeneously mixing and grinding 50 parts of N, merged, ^{2.5 part} by sloušniny C 3 says ^profiles of polyoxyethylene alkylaryl ether, 3 parts lignosulfonate, ^p enatého weighing ³⁰ parts. . silicon dioxide and 11.5 parts of fine-powdered clay. .

Example 7

Wettable powder

A wettable powder is prepared by homogeneously mixing and grinding 5 parts of Compound B ^{y 50} d ^clay compound ^Y C ² alkyl сПШ · benzensuUfonáku solution, 3 parts of calcium lignosulfonate, 10 ďfto rozslvkové earth -a ^{30d clay} finely ^{P RA Star} metal -hhnky .

Example 8

Emulsion

The emulsion is prepared by homogeneously entraining 10 parts of compound A, 20 parts of compound C, 0 parts of polyoxyethylene alkylaryl ether, 4 parts of sodium alkyl aryl sulfonate and 60 parts of dimethylformamide.

Example 9

Emulsion

The emulsion is prepared by homogeneously utterance '30 parts of Compound B, 5 parts of Compound C, 4 parts of sodium alkylarylsulfonate, 6 ^Di l ^{of the poly} oxyethylenalkylar ^yl ether and 55 dl ^ suhoxíáu ďtoeth ^profiles.

Example 10

Granule

The granular composition is prepared by homogeneously sieving and grinding 5 parts of compound A, 5 parts of compound C, 2 parts of polyvinyl alcohol, 15 parts of diatomaceous earth and 73 parts of clay, kneading the mixture obtained by grinding with water, granulating the resulting paste and drying of the resulting granules.

She said aii

Granules ^ Ostředek in ^p o ^d OIB ^{g of} Ranuli. se. pripr.av ^I by dissolving 10 - parts of compound A and 0.5 parts of Compound C - in - 3 parts (dimethylformamide drink offering thereon - 86.5 parts of diatomaceous earth in the form of granules obtained solution.

Example 12

Granule

Composition in the form of granules. is prepared by homogeneous drilling and grinding 1 part of compound - B1. 10 parts of compound C, 1 part of sodium alkylbenzene sulfonate, 5 parts of silica, 50 parts of bentonite and 30 parts of talc, by kneading the resulting mixture, granulating the mixture and drying the resulting granules.

Example 13

Dust

-Se powder composition prepared homogeneous шш promteemm ^- grinding the compounds Β ³ days, 1 - parts of Compound C, 0.5 parts kyshčrnku ^to Kamstrup th ^{or 95.5} - ^di- lu Minka.

Example 1 - d 1 4

Dusts ^{p ras} AC prostrata ^d e ^k p ^of ip.rav ^{homo g} enrnm promísernm and grinding 8 parts of Compound A, 0.5 parts of Compound C, 15 parts of diatomaceous earth, 50 parts of clay and 26.5 - part of talc.

Example 15

Dusts ^p ck ^šk AC ^{class P} ros e ^d e ^k are ^also prepared by homogeneously mixing and grinding 0.5 part of compound ^{No. 5} enyne ^y fy ^part of ^- enyne compound ^{No. y} fy ^{2 DI} l křemičitého- ^of carbon and 94.5 parts of clay .

In said ^forward e ^comm ladec ^h are described tests results demonstrate vynikajtá herhicidm ^tp efficiency can rost ^of the antifungal invention. In each test, tests were performed using each of these active compounds individually kteréžto- tests demonstrate their insufficient herbicidal úmnnosh and ^can le ^- test ^N. alkyl in which ^{the LO} oužito- combination of these 'compounds of the invention which has higher -with a herbicidal effect than just the sum of the efficacy of the individual compounds in a wide variety of weeds.

Example 1 -ad - 16

This example illustrates the herbicidal activity in a number of undesired weeds, as well as the phytotoxicity of the compositions of the invention to sugar beet during pre-emergence application. After <30 seeds of sugar beet. . (Beta vulgaris), hedgehogs (Echinochloa crusgalli), meadow-grass (Poa annua), fleabane (Plygons. Tepathitolium) and white merit (Chenopodium album var. Centrorubrum Makino) are sewn into ^the soil contained in each potyeth ^ ene n ^Aad ob ^ZDY in an area of 2000 cm ^{second P} o ^{p y} ocher three seeds Pooh ^d ou on it ^to uniformly nastnka and ^ZD characterized smáčiíelnýOi of powders along by Examples 1 and 3, after the ^{IB d} e z ^of n ^{Before eh eh} for water to obtain a solution of o- the concentrations of the active compounds listed in Table I at an application rate of 500 htr / ha. ^P o ^y UPL force ²⁵ days after the spraying, the fresh weight was determined textovaných plants from which, according to the following equation calculates the percent inhibition of growth:

growth inhibition (%) ^- = ⁽¹ fresh weight of plants grown on the examination procedure ^{br s} bow fresh weight proportioned ^{characterized} rostíé of untreated soil) X. 100 (III) ¹ The results are given in Table I. For comparison, similar tests were carried out in which each of the compounds after in applied composition applied separately under 'the same conditions as hereinbefore described; the results are also shown in Table I.

Table I

Herbicidal efficacy and phytotoxicity to sugar beet in pre-emergence application compound application growth inhibition (%) dose of barley beetroot rdes-no goosefoot (kg / ha) diabetes corn feet annual flea white

AND 3 0 В 3 0 C 2 0 C 1 0 AND 3 4- 0 C 2 AND 3 + 0 C 1 В 3 + ' 0 C 2 в 3 + · 0 C 1

89 86 23 19 Dec 81 83 25 20 May 23 63 100 ALIGN! 100 ALIGN! 6 20 May 80 ⁷⁹ 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN!

Example 17

This example illustrates the herbicidal activity of the compositions of the invention on various unwanted weeds and its phytotoxicity to sugar beet in post-emergence application. In each of the 2000 cm ² polyethylene containers filled with soil, sugar beets (up to 1.5 to 2 leaves), hedgehogs corn (up to 2 to 2.5 leaves), and annual meadow-grass (up to .1) are grown. , 5 to 2 sheets), rdesTable 11 no flea (up to 1 to 2 leaves) and white goosefoot (up to 2 to 2 leaves).

Each of the wettable powders prepared in Examples 2 and 4 was diluted with water to the active compound concentration given in Table II, and the resulting compositions were sprayed with stems and leaves of said plants at an application rate of 500 leaves / ha. Twenty days after spraying, the fresh weight of the plants was determined from which the percentage inhibition of growth according to formula III was calculated. The results are shown in Table II.

Herbicidal efficacy and phytotoxicity to sugar beet when applied to the stems and leaves in the growth stage compound application growth inhibition (%) dose of beetroot piggrass linden grass grassy (kg / ha) diabetes corn leg annual flea white

AND 4 0 78 70 13 10 В 4 0 75 70 16 14 C 2 0 8 14 56 59 C 1 0 4 9 32 40 AND 4 + 0 100 ALIGN! 100 ALIGN! 98 100 ALIGN! C 2 AND 4 + 0 96 100 ALIGN! 86 93 C 1 (B) 4 + 0 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! C 2 в 4 + 0 95 100 ALIGN! 85 96

NO. 1

219S47

Example 18

This example illustrates the herbicidal efficacy of the compositions of the invention on green shrew (Setaria viridis Beauv.) And white amaranth (Amaranthus albus) in pre-emergence and post-emergence applications. The seeds of the test plants are sown on the soil surface of a 2000 cm ² polyethylene container and covered with a 0.5 cm layer of soil 0 '. Each of the wettable powders prepared in Examples 5 and 6 was diluted with water to the active compound concentrations shown in Table III, and the compositions thus obtained were treated with the soil in pre-emergence and respiratory tests. These compositions are sprayed onto the stems and leaves of the plants at said growth stage at a post-emergence application rate of 500 liters / ha.

Twenty days after spraying, the fresh weight of the test plants was determined from which the inhibition of growth in percent according to formula III was calculated. The results are shown in the table

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Claims (1)

OBJECT OF THE INVENTION A herbicidal composition comprising, as active ingredients, a thiocarbamate derivative of the formula (I), wherein the other is a chlorine atom, and 4-amino-3-methyl-6-phenyl-1,2,4-triazine-5 ( 4H) -one of formula II (1) wherein one of X and Y is vo in a weight ratio of 1: 0.05 to 1: 10, wherein the active ingredients are present in a weight concentration ranging from 0.5 to 80% .