DD152275A1 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal agents, in particular for cereal cultivation. As active ingredients, they contain salts of the known 4-amino-benzenesulfonyl-carbamic acid residues R. The herbicidal compositions show improved selectivity and in the limit concentrations a stronger herbicidal activity.

Description

VEB CHEMIEKOMBINAT BITTEEFELD 'Bitterfeld, July 3, 1980

2085

Herbicidal agents

 Field of application of the invention

The invention relates to herbicidal compositions for controlling monocotyledonous and dicotyledonous weeds, in particular for growing cereals,

Charak teristik of be known technical solutions

The use of sulfonylcarbamic acid esters as herbicides is known

Thus, in DE-AS 1 468 220 herbicidal compositions of the general formula

Y f ~ ^ ~ SO ₂ MH-C (O) OCH _3,

in which Y = tert-nitro, amino, methoxycarbonylamino,

Methyl aminophenyl or H-methylformamylamino

means ^ or their alkali metal, ammonium, or amine salts described.

DE-A 1 468 310 also discloses the alkaline earth salts of these sulfonylcarbamic acid esters. ,

The use of the alkali and alkaline earth salts "brings advantages over the esters of water" in terms of good water solubility and the possible combination with other highly effective herbicides, for example, the salts of Phenoxyalkancarbonsäureo. However, both the sulfonylcarbamic acid esters and their alkali metal and alkaline earth metal salts are not sufficiently selective and are also insufficiently effective in the limit concentrations.

The aim of the invention is to develop, on the basis of sulfonylcarbamic acid esters, especially herbicides which are effective for growing cereals, which, in doses which are harmless to the crop plants, enable a good control of monocotyledonous and dicotyledonous weeds. '

presentation; of the essence of

The object is achieved in that the herbicidal compositions in addition to conventional excipients and carriers as the active compound compounds of the general formula

X / XN - - (/% -SO ₂ NH-

in which X stands for an inorganic or organic acid residue and, for example, Br ^e , N0 ₃ ^e , HSO ₄ ^e , H ₂ PO ₂ P, EgN-SO ₄ ®

CH ₃ OOcP, ClCH ₂ COCp, HOOC-COO ^ and R-may be,

contain. *

The active compounds according to the invention are prepared in a known manner, that is sulfonylcarbaminsäureester in

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diluted acids first dissolves, then precipitate by increasing the acid concentration, the crystalline salts. But it is also possible to use the aqueous solutions directly as herbicides · Some of the compounds shown in Table I.

Table I: Inventive active substances

e - e Y HW XH ₃ N β X SO ₂ KHO (O) OOH ₃ S Analysis ® ^. ' I h Cl , 32 Bez. 3? ( ⁰ ) "us N 13 , 92 e Cl 12 80 C 230-1 10.92 12 NO, 10.65 1 ^, 33 F 175 10.52 14.10 10.0 13.96 9.88 _8t 75 K HOOO-000 206-8 9.82 8.59 8.53

The herbicidal compositions of the invention have the same or better herbicidal action against the compounds described in DE-AS 1 468 220 and in DE-AS 1 468 310 a better selectivity to crops.

When used as herbicides, the active ingredients can be dissolved in water or mixed with dispersants used as a wettable powder. In the pre-emergence procedure, the application was carried out with winter barley until 2 days after sowing

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Winter wheat up to 5 days, sowing ₉ immediately after sugar beet, sowing and potatoes until 8 days after planting. The postemergence application was carried out in autumn or spring at the developmental stages indicated in Example 2, depending on the sowing date of the crops took place at the time before the start of the generative stage of the crop plants, as the weeds and weeds could not exert any negative influence on the crop plants »

Expiry Date e

Example 1 ϊ

For the investigation of the herbicidal effect in the pre-emergence application was carried out on arable land (sandy loam soil) in arable crops (winter barley, winter wheat, sugar beet and potatoes). The mono- and dicotyledonous weeds may also be in the cotyledonous stage at the time of application.

3 to 8 kg of active substance per hectare were used as 20 or 50% spray powder or as a solution in 600 l water / ha.

The crops and weeds or grass weeds listed in Table II were used to assess the control success and the tolerability:

2085

Table II:

Name of the crops, weeds or weed grasses used in the experiments · "

I Bigg II ' winter wheat III sugar beets IY potatoes V Foxtail grass VI Windhalm VII Ruched Ruchgrass VIII HühnerMrse IX Shepherd's Purse X White goosefoot XI corn marigold XII Genuine fume XIII cleavers XIV Stem-covered pigeon nettle XV Purple Deadnettle XVI Real chamomile XVII buckwheat XVIII wild radish XIX Common Ragwort XX charlock XXI chickweed XXII Thlaspi arvense ΧΣΙΙΙ Odorless beach chamomile XXIV Efeuehrenpreis XXV field pansy

Hordeum vulgare Triticum aestivum Beta vulgaris Solanum tuberosum Alopecurus myosuroides Apera spica-venti Anthoxanthum puelii Echinochloa grus-galli Capsella bursa-pastoris Chenopodium album Chrysanthemum segetuni Fumaria officinalis Galitun aparine Lamium amplexicaule

Lamium purpurcum Matricaria chamomilla Polygonum convolvulus Raphanus raphanistrum Senecio vulgaris Sinapis arvensis Stellaria media Thiaspi arvense Tripleurospermum inodorum Veronica hederifolia Viola tricolor arvensis

The evaluation of the control success and the compatibility was made according to the notes 1 to 9. Mean:.

1 = totally damaged '

9 = undamaged ·

Me other values are classified accordingly between the extremes ·

The results of the numerous experiments are given in Table III.

Mean in it?

A s N- (4-aminobenzenesulfonyl) methylcarbamate)

) from DE

, ν _Λ «λ) from DE-

from A ^ 1468220

C S hydrochloride of A erfindungsgemäBe agents

The hydrobromide of A ""

E = SuIf afc of A ·· "

Nitrafc from A ""

G = 5 aminosulfonate of A " ^M

H s phosphate from A ""

J a acetate of A "."

Ea Osalat from A ⁿ "

Table III: Herbicidal pre-emergence application of the agents of the invention

aO Plant tolerance and action against monocot. weeds

2085

no. no. Active substance On wall (kg / ha) Crops I II III IV 9 9 9 monocot V VI VII 9 9 VIII 1 unheated. - 9 9 7 7 4 2 2 9 8 8 9 8 3 8 7 4 9 2 A 3 5 8 9 7 6 7 8 4 3 7 6 9 6 3 5 4 6 9 8 6 3 B 5 8 7 7 9 9 • β 9 9 6 4 3 2 3 2 8 7 4 C 5 8 9 8 9 8 - 9 9 3 2 4 2 3 7 5 D 8th 9 8 9 9 - M 5 3 3 6 3 - 6 e 3 5 9 9 9 9 - 9 9 5 3 ro ro 4 1 - 7 P 3 5 9 9 9 9 - - ro ro OJOj 3 2 «A» 8th ^G 5 8 9-9 9 9 - 9 9 2 2 OJOJ 3 1 9 H 5 8 9 9 9 9 - - ro ro 4 3 4 2 - 11 J 8th 9 9 9 9 OO CN 9 9 3 3 3 2 2 9 9 12 K 8th 9 9 4 2 7 5

ο M • Η

H H

H H

H H H

H H

H H

H'cö

α α bo cö co ^ j

ρ-tsl

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• Ρ ', Ο «5 ίί -P W CQ

CO

CTn CTNCNlA VDLTs ^ J- (Λ LAC "\ CO Φ OO LA

CTn CTNLA4 ·

CTN = J ·

iJ-C \ J

CM

IAC \ VD ^ f ΙΑΓΛ

C7N.C0Ds.fA 00 4 · ii-CNJ ij-CXi (JNVD D-IA LACNJ CA \ - VO CA C \ lr

CTn CTnCOLA CQvD CO ij OMA CTnLA CTnCN cTnCN OO IA CTnCN CO CN

CTn

4 "CA CAC \] <f- CM CNCA VO CA CXJ CXJ CVJr * CACVJ

CTn OO LAfA IA4-

CA CMA CN ^ f ¹ 4 ¹ CM CACU lAOJ CACVJ

On CNCACM CACVJ CACVj 4 · CA CNfA VDCA CM CM CMc-4-CVl CACM

CT \ CTNCN4-OO LA U) 4 "Φ 4- CTnLA CTnLA LAcA LACA VO 4 * 4" CA.

CTn OO 4-CM LACA 4 "CA 4" CA CO CA CNCA CACM CMOJ VD CA 4 "CVJ

CTN COvOCA CN4-IACM LACA CnLA VD 4-4-OJ CAOJ LACA 4 "CA.

CTn COLAfA LA4 "LACM IAfA CN4 * VO 4-4 · CM 4-CM LAfA 4-CA

CTn CTNCTNCTn CTnCTN CTNCN CTnCO CTnCTn CTnCTn CTnCTn CTnCTn CTnCTn CTnCTn

CTn CTNCN4 · VDLA CNfA OO CA CNLA CNLA IACV] LA CA VO 4 "4" CVJ

CTn cnlacm lt \ ca 4-oj vd ca vD4- iaca cacm cav 4-cvi cm cm

CTn CO CNfA VD CA IACM 4 * CVJ CN4 * CN4 "IACVJ 4" V * LAfA CVI V "

I CALAOO LACO LACO LAOO CAlA CAtA LfN ₁ CO LA «) IACO LAOO

Xi

Q)

ΰ " ³ I PQ Ό

V OJ CA

LA VO CNOO CTN

£ 902

It can be seen from Table III that the agents according to the invention have the following advantages over the known comparison compounds A and B:

- All tested compounds show a better crop tolerance compared to A and B.

, (Winter barley, winter wheat and potatoes show no phytotoxic effects)

- The efficacy against monocotyledonous weeds (especially Windhalm) and dicotyledonous weeds is better than that of comparative compounds A and B.

The compounds 3?, G and H _e proved to be particularly effective

Example 2?

For the investigation of the herbicidal effect in the post-emergence application, the application was made on arable land (sandy loam soil) in cultivated plant stands (? / Intergerste and winter wheat).

The crop plants were in the 2- to 4-leaf stage at the time of application, the weeds predominantly in the germinal to 2-leaf stage

3 to 8 kg of active substance per hectare were used as 20 or 50% spray powder or as a solution in 600 l water / ha.

The results are summarized in Table IV. The active substances and plants listed herein correspond to the details in Tables II and III, respectively.

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Table IVs Application of the agents according to the invention in the Kachauflaufverfahren

lid. Act iv Expenditure-· crops II weeds XIII No. ₀ substance amount 9 9 kg / ha I 8th VI. 9 1 unheated. " - 9 5 • 9 9 2 A 3 8th 1 6 9 6 5 3 9 3 B 3 8th 9 6 8th 5 9 4 7 e 3 9 9 3 7 9 9 2 5 5 G 3 9 2 9 1

And G over the known compounds A and B, the following advantages besitzenϊ ^- from Table IV that the compounds E can be seen,

Compounds E and G show a very good plant tolerance compared to A and B.

"Furthermore, the efficacy against monocotyledonous weeds (especially Windhalm) in the tested expenses is very good ₉ while the compounds A and B are not sufficiently effective or let Mt increasing amount of expenditure detect lack of selectivity.

Claims (1)

J? ItJVvf & 3 · - 11 - 2085 invention claim Herbicidal agents, in particular for growing cereals ^ characterized in that they, in addition to customary auxiliaries and d'r ag er substances as the active compound compounds of the general formula X £ ~ Ε _Ο Ή «/ \ - SO ₂ MC (U) OCH ₃ J in the X for an inorganic or organic acid radical, such as Cl ^e , Br ^e , NO ₃ ⁶ ", HSO ₄ ⁶ *, H ₂ PO ₄ ^, H ₂ K-SO ₃ ^, R ^ C ₆ H ₄ SO ₃ ⁰ , CH ₃ COO ^, ClCK ₂ C00 ^e _? HOOC-COd ^, RC ₆ H ₄ -CH ₂ C00 ^e is contained.