DD157750A5 - HERBICIDE MEDIUM - Google Patents

Abstract

A herbicidal composition comprising a compound of the formula A in which X is chlorine or bromine, Y is hydrogen when X = Cl, or chlorine when X = Br and Z (C deep 1-C deep 4) alkyl, in combination with a compound of the formula B in which R is bromine or iodine, R 1 is hydrogen, an alkali metal or ammonium cation or (C 1 - C deep 8) alkanoyl, as active ingredients, wherein the weight ratio of the compounds of formula A to formula B is preferably 1: 0.05 to 1: 5, characterized by a synergistic effect especially against broadleaf weeds in cereals.

Description

The invention relates to herbicidal compositions, in particular for controlling weeds in cereal crops, '

Characteristic of the known technical solutions

It is already known that the compound 2-4- (4 ^l -chlorophenoxy) -phenoxy3-propionic acid isobutyl ester (II) is effective against a number of grassy weeds, for example field foxtail, in the pre- and Naohäuflauf (DE-OS 22 23 894) "The same has been reported for the compound 2 - ^ [4 ^ (2 ^! ^ Chloro-4 ^l -brompheno3cy) -phenoxy ^ -propionic acid methyl ester Cl) with regard to plughafer, Ackerfuclisschwanz and certain Hirsearten (DE-OS 26 01 548) "The selectivity, ie harmlessness of the compounds to selected cereal crops, should be emphasized.

It is further known that 3,5-dihalogeno-4-hydroxysobenzonitrile, 3B, ioxynil (3,5-diiodo-4-hydroxybenzonitrile) and bromo-oxynil (3,5-dibroin-4-hydroxybenaonitrile) , as weed control agents in cereals use (WL-OS 64II.452).

In the usual application rates, the effect of the substances mentioned is good, but they are not all common in cereals

209248 -2- Berlin, d.27.3.1979

AP A O1H / 2O9 248

occurring weeds. Thus, the effectiveness of the compounds (I) and (II) is strictly limited to grass weeds, broadleaf weeds are not damaged or only to a very minor degree. Conversely, although loxynil and bromoxynil are very effective against a number of broadleaf weeds such as chamomile or melon, they are ineffective against grass weeds.

Object of the invention

The aim of the invention is the provision of herbicidal agents with a broad spectrum of activity and good compatibility with cereal crops which are suitable for combating monocotyledonous and dicotyledonous weeds. "

Presentation of 7 / esens the invention

The invention has for its object to find suitable compositions which are equally suitable to combat broadleaf and grassy weeds, but are harmless to cereal crops.

In combination experiments with the known mixtures, it has now surprisingly been found that combinations of (I) or (II) with ioxynil or bromoxynil form a superadditive, d. have synergistic effects when applied to broadleaf weeds in cereals.

The invention thus herbisidic effective combinations are characterized by a content of a compound of the general formula

-CH COOZ (A)

.209248 -3- Berlin, a. 03/27/1979

AP £ O1N / 2O9 248

in which

X is chlorine or bromine,

Y is hydrogen when X is Cl or chlorine when X is Br and Z (CjC.) Alkyl

in combination with a compound of the formula

(B)

in which

R is bromine or iodine

RJ is hydrogen, an alkali or ammonium cation or (C ₁ -Cg)

Alkanoyl, as effective components

The compounds of formula A are in particular

I 2-j4- (2'-chloro-4'-bromophenoxy) -phenoxyj-propionic acid "- methyl ester, and

II 2 ~ [4- (4 ^l -ChlorphenoxyJ-phenoxyJ propionic acid-isobutyl ester.

The compounds of the formula B are, in particular,

III 3,5-diiodo-4 ^ hydroxyben3onitrile (loxynil), also its sodium, potassium or ammonium salt or its ootanoate, and

IV 3 »5-dibromo-4-hydroxybenzonitrile (bromoxynil) or its sodium or its octonoate

The synergistic effect of the combinations according to the invention is particularly pronounced when used against broad-leaf

8-4- Berlin, d. 27.3.1979 AP A 01IT / 209 248

weeds. By adding a compound of the formula (A), therefore, the application concentration of a compound of the formula (B) required for successful control of dicotyledonous weeds can be considerably reduced.

The combinations of the invention are particularly suitable for controlling annual weeds in V / inter- and summer cereals, in particular of reporting, chamomile, Klettenlabkraut, Arableweed, and wild oats. The mixing ratio (A): (B) can vary widely, between 1: 0.05 and 1: 5. Preferably, the mixing ratio (A): (B) is between 1: 0-1 and 1: 1. The total requirement Application rate (A) + (B) is on the order of 0.5 to 2 kg / ha.

The compositions according to the invention may be formulated in the form of wettable powders, emulsifiable concentrates or dusts and contain customary formulation auxiliaries, such as wetting agents, tackifiers, dispersants, solid or liquid inert substances, and grinding aids or solvents.

The following may be used as carriers: mineral substances such as aluminum silicates, clays, kaolin "chalks, silicates, talc, kieselguhr or hydrated silicic acids or preparations of these mineral substances with special additives, for example, chalk greased with sodium stearate. As carriers for liquid preparations, it is possible to use all customary and suitable organic solvents, for example toluene, xylene, diacetone alcohol, isophorone, benzines, paraffin oils, dioxane, dimethylformamide, dimethylsulfoxide, ethyl acetate, butyl acetate, tetrahydrofuran, chlorobenzene and others.

20 9 2 & 8 -5- Berlin, d.27.3.1979

AP A O1N / 2O9 248

As adhesives, glue-like cellulose prodrugs or polyvinyl alcohols can be used.

Suitable wetting agents are all suitable emulsifiers, such as oxaethylated alkylphenols, salts of aryl or alkylarylsulfonic acids, salts of ethoxylated benzenesulfonic acids or embossed soaps;

As Mspergierstoffo are suitable cell pitch (salts of sulfite liquors), salts of Naph.thalinsulfonsau.re and possibly hydrated silicic acids or kieselguhr,

Ala grinding aids may be used, or suitable inorganic salts such as sodium sulfate organisehe _f ammonium sulfate, sodium carbonate, ITatriumbicarbonat, sodium thiosulfate, sodium stearate, sodium acetate.

The content of these agents in the active compounds according to the invention is generally between 2 and 85%. Before application, the agents are brought to the desired application concentration by addition of a suitable solvent or diluent (usually water),

Auaführun g s s at pie l

The invention will be explained in more detail below on some embodiments.

Pure simple formulations suitable for the effect tests can be obtained, for example, according to the following instructions:

20 92 - 6 - Berlin, d.27.3.1979 AP A 01U / 209 248

Example 1:

15 Parts by weight 16 · Weight parts by 15 · 1 Parts by weight 10.0 Parts by weight 29.0 Weight "parts by 6.5 Weight "parts by 4.5 · Weight parts by Example 2:

22.0 parts by weight 16.0 parts by weight

10.0 parts by weight

27 x 9 parts by weight

11.0 parts by weight

9.0 parts by weight

Compound I (calculated on pure substance)

Compound IV as octenoate (calculated on pure active substance) contains 56 % IV as free phenol (corresponding to 9 parts by weight).

Fatty alcohol polyglycol ether cyclohexanone

Xylene Mixture of dodecylbenzenesulfonic acid calcium and alkylphenyl polyglycol ether Castor oil polyglycol ether

Compound I (calculated on pure active compound) compound IV as octenoate (calculated on pure active substance); therein contain 56 % IV as free phenol (corresponding to 9 parts by weight) of cyclohexanone

Xylene.

Castor oil-polyglycol etheric mixture of dodecylbenzenesulfonic acid calcium and alkylphenyl polyglycol ether

The synergistic effect of the active ingredient combinations is evident from the following examples. While the individual active ingredients have leucogenics in the herbicidal action, the combinations show a broader weed effect, which goes beyond a simple action summation.

A synergistic effect is always present when the effect of the active ingredient combinations is greater than that of the

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AP A O1N / 2O9 248

individually applied active ingredients. The expected effect for a given combination of two herbicides (see Colby, S.R., "Calculation synergistic and antagonistic responses of herbicides, combinations", "Weeds 15, 1967" p.20-22) can be calculated as follows:

if X = % damage by herbicide A at χ kg / ha application rate and Y s % damage by herbicide B at $ kg / ha application rate, the expected damage to combination A + B is calculated at (x + y) kg / ha application rate from the formula

ε = x + y

TOO

If the actual damage is greater than E, then the combination is more than additive in its effect, that is, there is a synergistic effect, as demonstrated in the following examples. "

Example 3i

In a greenhouse experiment, various weeds were after emergence with the compounds I, III or IY treated and with d.en combinations I + III + IV and I · The result is shown in the following table. In this case, the effect was generally stated in % damage, and the combinations also differentiated between the calculated effect according to the above formula (in brackets) and then the actual effect found,

C \ C \

(for example 3)

Treatment dosage in kg / ha

kg / ha of hydroxybenzonitrile (III or IV). 0.075 0.15 0.3

0.6

a) Chenopodium album (report)

III

0.72 I + .III 0.54 II + III

IV

0.72 I + IV 0.54 II '+

0 9 5 0

9 5

(27.2) · (24)

(59.96) (58.2)

(31.75) (28.75)

(98.18) (98.1)

25

100

75

98th

98

100

(58 * 14) (56.3)

(100) (100)

54 100

82 100 100 100

(94.54) (94 * 3)

(100) (100)

94 100

99 100 100 100

b) Katricaria chamomilla (chamomile.)

0.72

0.72

III

I '+ III

IV + IV

5 0

(24) (28Γ75)

(43) (527s)

40 - 60

70 (62) 75

50 - 75

75 (76.25) 90

(85.75)

ά) Avena fatua (flying oats)

III

0.09 I + III

IV

0.09 I + IV

52

52 (56.32) (567s)

85

97

  90

100

0) Galium aparine 0 mm 57) 13 ¹ ' im 8th) 20 ·· * 37) 33 , (55 .5)   50 fe (Cleavers) 11 (22nd 30 (28th 40 (40th 50 • 80 III !> O 0.72 I + III

70 10 72

VjJ ΓΟ ·

00 VJi

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AP A 01K / 209 248

The comparison between the found and calculated effect clearly shows the synergistic effect.

Example 4s

In a greenhouse compatibility test on summer wheat and barley it was shown that the individual treatments as well as the combinations did not damage the mentioned crops.

kg / ha _ P, raparat summer wheat Sommergerete

0'0

0 0

0 0

0 0

0 0

0 0

  ο o

0 0

0.72 I- 0.54 II 0 * 6 III 0.6 IV I + III I. + IV II +. III II + IV

Claims (5)

0 92 48 -10- Berlin, d.27.3.1979 AP A O1U / 2O9 248 Brfindunp; sanaprtich 1. A herbicidal composition characterized by a content of a compound of the formula. O-CH COOZ (A) in which X is chlorine or bromine, Y is hydrogen, if X = Cl, or chlorine, if X = Br and Z (CjC ₄ ) alkyl in combination with a compound of the formula in which R is bromine or. iodine R-j is hydrogen, an alkali or ammonium cation or ν- '(C-j-Cg) alkanoyl, as active ingredients, in addition to extenders and / or surface-active agents, 2 O 3 2 4 8 - 11 - Berlin, a.27.3. AP A 01U / 209 248 B III) 3,5-diiodo-4-hydroxybenzonitrile or its sodium, K or IiH. Sals or its octanoate, or IV) 35> 5 - dibromo-4-hydro: x: ybenzonitrile or its Na-SaIa odor its octanoate as active ingredients. 2. Herbicidal agent according to item 1, characterized by a Salary , AI) 2- ^ 4- (2 ^! -Chloro-4'-bromophenoxy) -phenoxyJ-propion acid methyl ester or II) 2- Γ4- (4'-chlorophenoxy) -phenoxy "] -propionic acid iso- Butyl ester in combination with 3 * herbicidal compositions according to point 1 and 2, characterized in that the mixing ratio (A): (B) in the range of 1 ι 0.05 and 1: 5, 4. A herbicidal composition according to item 1 and 2, characterized in that the mixing ratio (A): (B) in the range of 1: 0.1 and .1: 1. 5 x \ ^r Before Using compositions according to the points 1-4 "characterized in that they are used for the control of dicotyledonous weeds in cereal monor and cultures.