CA1123220A - Herbicidal compositions - Google Patents
Herbicidal compositionsInfo
- Publication number
- CA1123220A CA1123220A CA317,863A CA317863A CA1123220A CA 1123220 A CA1123220 A CA 1123220A CA 317863 A CA317863 A CA 317863A CA 1123220 A CA1123220 A CA 1123220A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- chlorine
- herbicidal compositions
- bromine
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
HERBICIDAL COMPOSITIONS
Abstract of the disclosure:
Herbicidal compositions containing a compound of the formula A
(A) in which X is chlorine or bromine, Y is hydrogen, if X is chlorine, or is chlorine, if X is bromine, and Z is (C1-C4)-alkyl, in combination with a compound of the formula B
Abstract of the disclosure:
Herbicidal compositions containing a compound of the formula A
(A) in which X is chlorine or bromine, Y is hydrogen, if X is chlorine, or is chlorine, if X is bromine, and Z is (C1-C4)-alkyl, in combination with a compound of the formula B
Description
~.Z3ZZO
- 2 - HOE 77/F 244 The present invention relates to herbicidal compo-sitions.
It has already been described that the compound 2-/ 4-(4'-chlorophenoxy)-phenoxy 7-propionic acid-isobutyl ester (II) is active against a series of weed grasses, for example annual blackgrass (Alopecurus myosuroides), in the pre- and post-emergence application (German Offenlegungs-schrift ~o. 22 23 894). Similar facts were reported for the compound 2-/ 4-(2'-chloro-4'-bromophenoxy)-phenoxy 7-propionic acid-methyl ester (I) with regard to wild oats - (Avena fatua), annual blackgrass and certain types of millet (German Offenlegungsschrift No. 26 01 548). There is to be mentioned especially the selectiYity, i.e. the harmlessness of the compounds to determined cereal cultures.
It has further been described that 3,5-dihalogeno-4-hydroxy-benzonitriles, for example ioxynilet3,5-diiodo-- 4-hydroxybenzonitrile) and bromoxynile(3,5-dibromo-4-hy-droxybenzonitrile), are employed as herbicidal composi-tions in cereals (Netherlands Offenlegungsschrift No.
6411 452).
In the usual amounts applied, the above-mentioned sub-stances show a good activity, however, which does not cover all the weeds frequently occurring in cereals. Thus, the action of compounds (I) and (II) is strictly limited to weed grasses, whereas broad-leaved weeds are not affected at all or only to an insignificant degree. On the other hand, ioxynile and bromoxynile show a very good action against a series of broad-leaved weeds, such as 29 wild camomile (Matricaria charnomilla) or common orache '' ~
:: , , ~.Z32ZO
~Chenopodium album), however, they are ineffective towards weed grasses.
In combination tests with the above-mentioned mixtures it has now surprisingly been found that combinations of ~I) or ~II) with ioxynile or bro-moxynile show a more than additive effect, i.e. a synergistic action, when used against broad-leaved weeds in cereals.
The present invention therefore provides herbicidally active combin-ations which contain as active ingredients a compound of the general formula ~A) X ~ _ o - ~ C~l3 in which X is chlorine or bromine, Y is hydrogen, if X is Cl, or is chlorine, if X is Br, and Z is ~Cl - C4) - alkyl, in combination with a compound of the formula R ~B) RIO ¦ ~ Y C - N
in which R is bromine or iodine, Rl is hydrogen, an alkali metal cation or an ammonium cation or ~Cl - C8) - alkaonyl, wherein the mixing ratio of ~A) to ~B) is in the range of from 1:0.05 to 1:5.
As compounds of the Formula A there may be mentioned in particular _3_ - : :
- : ~
- :-' - ~ `: ' ~.Z~Z20 I 2-/ 4-(2'-chloro-4'-bromophenoxy)-phenoxy 7-propionic acid-methyl ester, and II 2-/-4-(4'-chlorophenoxy)-phenoxy 7-propionic acid iso-butyl ester.
As compounds of the formula B there may be mention-ed in particular III 3,5-diiodo-4-hydroxyben~onitrile (ioxynile), further-more the sodium, potassium or ammonium salts thereof or its oct~oate~
as well as I~ 3,5-dibromo-4-hydroxybenzonitrile (bromoxynile) or its sodium salt, or its oct~oate.
The synergistic effe^t of the combinations of the in-vention becomes evident in particular in the use against broad-leaved weeds. By adding a compound of the formula (A)`, the application concentration of a compound of the formula (B), which is required for the successful combat-ing of dicotyledonous weeds, may thus be reduced consi-derably.
The combinations of the invention are particularly suitable for the combating of annual weeds in winter and spring cereals, especially of common orache, wild camomile, cleaver, annual blackgrass and wild oats. The mixing ratio of (A) to (B) may vary within a wide range, from 1:0.05 to 1:5. Preferably the mixing ratio of (A):(B) is in the range of from 1:0.1 to 1:1. The amount applied of (A) +
(B) which is required altogether is in the range of from 0.5 to 2 ~cg/ha.
29 The agents of the invention may be formulated as wet--: -~ 3Z20 table powders, emulsifiable concentrates or dusting pow-ders, and they contain common formulation auxiliaries, such as wetting agents, adhesivest dispersing agents, so-lid or liquid inert substances, as well as grinding auxi-liaries or solvents.
As carrier materials there may be used mineral sub-stances, such as aluminum silicates, aluminum oxides, ka-olin, chalks, siliceous chalks, talc, kieselguhr, or hy-drated silicic acids or preparations of the aforesaid mi-neral substances with special additives, for example chalktreated with sodium stearate. As carrier materials for liquid formulations all common and appropriate organic solvents may be used, for example toluene, xylene, diace-tone alcohol, isophorone, gasolines, paraffin oils, di-oxan, dimethylformamide, dimethylsulfoxide, ethyl acetate,butyl acetate, tetrahydrofuran, chlorobenzene, and others.
As adhesivesglue-like cellulose products or polyvinyl alcohols can be used.
Suitable wetting agents are appropriate emulsi~iers, such as oxethylated alkyl phenols, salts of aryl or allcyl-aryl-sulfonic acids, salts of ethoxylated benzosulfonic acids or soaps.
As dispersing agents there may be used cellulose waste liquors ~salts of sulfite waste liquors), salts of naphthalene-sulfonic acid and in some cases also hydrated silicic acids or kieselguhr.
Suitable grinding auxiliaries are inorganic or orga-nic salts, such as sodium sulfate, ammonium sulfate, so-29 dium carbonate, sodium bicarbonate, sodium thiosulfate, - , - . ~ ~ ,, ~:
,: . : . . . ~ ` . ` `
, . ; , ' . ~: .
!.23220 sodium stearate, and sodium acetate.
In general, the active ingredients according to the present invention are contained in the herbicidal mixtures in amounts of from 2 to 85 %. Prior to their application, the compositions are brought to the desired application concentration by adding an appropriate solvent or diluent (in most cases water).
Formulations that are suitable for the effectiveness tests may be obtained in simple manner, for example~ according to the following prescriptions:
E X A M P L E 1:
Parts by weight of compound I ~calculated on the pure active ingredient) 16 parts by weight of compound IV as octanoate tcalculated on the pure active ingredient) 15.1 parts by weight of isotridecanol polyglycol ether (6 AEO) 10.1 parts by weight of cyclohexanone 29.0 parts by weight of xylene 6.5 parts by weight of a mixture of calcium dodecylbenzene-sulfonate and alkylphenyl-polyglycol ether ( ~ ATL,OX) 4.5 parts by weight of castor oil-polyglycol ether (40 AEO).
E X A M P L E 2:
22.0 Parts by weight of compound I (calculated on the pure active ingredient) 16.0 parts by weight of compound IV as octanoate (calculated on the pure active ingredient) :, -7_ ~.2~3~ZO
lOoO parts by weight of cyclohexanone 27O9 parts by weight of xylene 11.0 parts by weight of castor oil-polyglycol ether t~0 AEO) 9.0 parts by weight of a mixture of calcium dodecylbenzene-sulfonate and alkylphenyl-polyglycol ether ( ~ ATLOX).
The synergistic effect of the combinations of active substances becomes evident from the following Examples. Whereas the individual active ~` ingredients show some deficiencies in their herbicidal action, the combinations show a more extensive action on weeds which is more than a simple addition of effects.
A synergistic effect is present in those cases in which the action of the combinations of active substances is stronger than that of the active substances applied individually. The effect to be expected for a given combination of two herbicidal agents (cf. Colby~ S.R., "Calculation of synergistic and antagonistic ~esponses of herbicide combinations", Weeds I5 1967, pages 2Q to 22) can be calculated as follows:
If X represents the per cent of damage effected by herbicidal agent A with x kg/ha of amount applied and Y represents the per cent of damage effected by herbicidal agent B with y kg/ha of amount applied> the expected damage of the combination A + B with an amount applied of - -:. . . . ., - , : ,........... . ::: . . :
- .: - ~ :
,.
~v .
(x + y) kg~ha is calculated by way of the formula E = X + Y~
., ., ' . 100/
If the actual damage is greater than E, the effect of the combination is more than additive, i.e. a synergistic effect is produced, as has been demonstrated in the follow-ing Examples.
- E X A M P L E 3:
In a greenhouse test different weeds were treated after emergence with compounds I, III or IV as well as with the combinations I~III and I+IV. The result has been given in the following Table. The effect has gene~
rally been indicated in per cent of damage, and in the case of the combinations the results are shown both for the effect calculated in accordance with the above for-mula (in brackets) and subsequently for the effect ac-tually found.
- ~1.23ZZO
.
-` - 9 - HOE 77/F 244 ~ocs~ooo. L~ OO oo o~oo~
o o~ o o o .0 ~ o~ o r~ ) 1~
~D _~ ~ ,_ ~ ,_ ~
~ Ir~ N
O U~ ~ U~ ~ ~ 0 I ~ ~ 1 00 I . I . I . I . I .
=1' :3 0 0 Il~ O L~
'Cl~ ~ ~ CO cr~ 1~ I
_ _ _ _ _~ _ _ ~o~ooo Omu~o tno Lf~ O O~ O O O ~ r _~ ~_~ _~ _~
~ O ~ U~ ~
H ~ 1~ ~ N ~n I 1 00 1~ 1 . I . l l l l ~ OC> `D O O N ~ O
O L~ ~ ~
__ _~_ _ _ ~_ H .
H lS~ O Lr~ 0 0 0 O O O L~ O O
H C~l O t--C~ C~ O . ~ Lf~ c_ .- ~ .
a~
~ ~- ,~ ~_ .,~ . Ln L-~ 0 . ,_ S~ O C--~ ~, U~ 0 ~ I . . I . . I~ I . I .
~ ~ 0 0 oo ~ 0 S:: ~ CS~ O~ _`=t 11~ <~I
O _~_ __ _ _~ _ ~ _ D .
X O0 O~ O U~ O In ~ O ~O
O C~.l 0 ~O 1~ 0 0 N =r N Lf~ ,_ S~ ~ ~ ~ ~
O ~ Ll~
a~ ~ ~ L~
00 I .~ I . . l~ I . I .
1~3 ~0 ~ 0 N
nl N N U~ ~ 1 N
S __ __ _ _ _ Y
O O~ U~ O C~ U~ O ~ O Lt~ O ~ O ~ O ~
O . ~_ L~
.
~1 .,1 ~ O
~^ ~^
~1 0 ~ Q~
t~ 1 H H H ~ ~ ~ .C H H H ~ ~ ~: H H H H ~ ~
td C) H H H H H H 0 ~ H H H H ~--1 H H H H H H
~_S 6 ~t H H H 6 H H L H H t~--` H H
::S ~ t[~ O t~ 3 0~
b~ ~ O ~ + + + -~ E ~ ~ ~^
0~: ~ ~ td ~ ~I ~ ~
H O ~H HH H ~ C~ H H 0 H G~ O H H
C2. ~ ~C~. O H H 0 ~ :~
6~: rl O .~ ~1 ~~1~N =~ ~ ~ ~ l ~ Q) ~1 ~ ~1 O~
X6 0 ~ O~ In ~ 1~ ~ ~1 ~1 ~ O rt O O
b~ C~ C),, , . (~ 3 ' ' 1~ :~ .
O0 U~ ~_)--O O O O ~-- O O ~ O 'C~ O O
O ~ ~ ~ ~
E~ ~ ~ c~ ~
.
- : . ,~, ,, ' . , ' .' .: ' " ` . : ~ , -lU~ U
The comparison between the effect found and the calculated effect clearly shows the synergistic effectO
E X A M P L E 4:
.
In a compatibility test performed in the greenhouse with spring wheat and spring barley it could be proved that the treatment with the individual compounds as well as with the combined compounds did no harm to the crop plants mentioned above, k~/ha __ Preparation _ ~ _ g wheat _ Spring barley Q.72 I û 0 10 0.54 II o o 0.6 III 0 û
0.6 IV o o I +III ~0.72 kg/ha I + û.6 kg/ha III~ 0 û
I +IV ~0.72 kg/ha I + 0.6 kg/ha IV) û 0 II +III ~û.54 kg/ha II + 0.6 kg/ha III) 0 II ~IV (0.54 kg/ha II + 0.6 kg/ha IV) 0 0 . . . . -.,; ~ ;~
It has already been described that the compound 2-/ 4-(4'-chlorophenoxy)-phenoxy 7-propionic acid-isobutyl ester (II) is active against a series of weed grasses, for example annual blackgrass (Alopecurus myosuroides), in the pre- and post-emergence application (German Offenlegungs-schrift ~o. 22 23 894). Similar facts were reported for the compound 2-/ 4-(2'-chloro-4'-bromophenoxy)-phenoxy 7-propionic acid-methyl ester (I) with regard to wild oats - (Avena fatua), annual blackgrass and certain types of millet (German Offenlegungsschrift No. 26 01 548). There is to be mentioned especially the selectiYity, i.e. the harmlessness of the compounds to determined cereal cultures.
It has further been described that 3,5-dihalogeno-4-hydroxy-benzonitriles, for example ioxynilet3,5-diiodo-- 4-hydroxybenzonitrile) and bromoxynile(3,5-dibromo-4-hy-droxybenzonitrile), are employed as herbicidal composi-tions in cereals (Netherlands Offenlegungsschrift No.
6411 452).
In the usual amounts applied, the above-mentioned sub-stances show a good activity, however, which does not cover all the weeds frequently occurring in cereals. Thus, the action of compounds (I) and (II) is strictly limited to weed grasses, whereas broad-leaved weeds are not affected at all or only to an insignificant degree. On the other hand, ioxynile and bromoxynile show a very good action against a series of broad-leaved weeds, such as 29 wild camomile (Matricaria charnomilla) or common orache '' ~
:: , , ~.Z32ZO
~Chenopodium album), however, they are ineffective towards weed grasses.
In combination tests with the above-mentioned mixtures it has now surprisingly been found that combinations of ~I) or ~II) with ioxynile or bro-moxynile show a more than additive effect, i.e. a synergistic action, when used against broad-leaved weeds in cereals.
The present invention therefore provides herbicidally active combin-ations which contain as active ingredients a compound of the general formula ~A) X ~ _ o - ~ C~l3 in which X is chlorine or bromine, Y is hydrogen, if X is Cl, or is chlorine, if X is Br, and Z is ~Cl - C4) - alkyl, in combination with a compound of the formula R ~B) RIO ¦ ~ Y C - N
in which R is bromine or iodine, Rl is hydrogen, an alkali metal cation or an ammonium cation or ~Cl - C8) - alkaonyl, wherein the mixing ratio of ~A) to ~B) is in the range of from 1:0.05 to 1:5.
As compounds of the Formula A there may be mentioned in particular _3_ - : :
- : ~
- :-' - ~ `: ' ~.Z~Z20 I 2-/ 4-(2'-chloro-4'-bromophenoxy)-phenoxy 7-propionic acid-methyl ester, and II 2-/-4-(4'-chlorophenoxy)-phenoxy 7-propionic acid iso-butyl ester.
As compounds of the formula B there may be mention-ed in particular III 3,5-diiodo-4-hydroxyben~onitrile (ioxynile), further-more the sodium, potassium or ammonium salts thereof or its oct~oate~
as well as I~ 3,5-dibromo-4-hydroxybenzonitrile (bromoxynile) or its sodium salt, or its oct~oate.
The synergistic effe^t of the combinations of the in-vention becomes evident in particular in the use against broad-leaved weeds. By adding a compound of the formula (A)`, the application concentration of a compound of the formula (B), which is required for the successful combat-ing of dicotyledonous weeds, may thus be reduced consi-derably.
The combinations of the invention are particularly suitable for the combating of annual weeds in winter and spring cereals, especially of common orache, wild camomile, cleaver, annual blackgrass and wild oats. The mixing ratio of (A) to (B) may vary within a wide range, from 1:0.05 to 1:5. Preferably the mixing ratio of (A):(B) is in the range of from 1:0.1 to 1:1. The amount applied of (A) +
(B) which is required altogether is in the range of from 0.5 to 2 ~cg/ha.
29 The agents of the invention may be formulated as wet--: -~ 3Z20 table powders, emulsifiable concentrates or dusting pow-ders, and they contain common formulation auxiliaries, such as wetting agents, adhesivest dispersing agents, so-lid or liquid inert substances, as well as grinding auxi-liaries or solvents.
As carrier materials there may be used mineral sub-stances, such as aluminum silicates, aluminum oxides, ka-olin, chalks, siliceous chalks, talc, kieselguhr, or hy-drated silicic acids or preparations of the aforesaid mi-neral substances with special additives, for example chalktreated with sodium stearate. As carrier materials for liquid formulations all common and appropriate organic solvents may be used, for example toluene, xylene, diace-tone alcohol, isophorone, gasolines, paraffin oils, di-oxan, dimethylformamide, dimethylsulfoxide, ethyl acetate,butyl acetate, tetrahydrofuran, chlorobenzene, and others.
As adhesivesglue-like cellulose products or polyvinyl alcohols can be used.
Suitable wetting agents are appropriate emulsi~iers, such as oxethylated alkyl phenols, salts of aryl or allcyl-aryl-sulfonic acids, salts of ethoxylated benzosulfonic acids or soaps.
As dispersing agents there may be used cellulose waste liquors ~salts of sulfite waste liquors), salts of naphthalene-sulfonic acid and in some cases also hydrated silicic acids or kieselguhr.
Suitable grinding auxiliaries are inorganic or orga-nic salts, such as sodium sulfate, ammonium sulfate, so-29 dium carbonate, sodium bicarbonate, sodium thiosulfate, - , - . ~ ~ ,, ~:
,: . : . . . ~ ` . ` `
, . ; , ' . ~: .
!.23220 sodium stearate, and sodium acetate.
In general, the active ingredients according to the present invention are contained in the herbicidal mixtures in amounts of from 2 to 85 %. Prior to their application, the compositions are brought to the desired application concentration by adding an appropriate solvent or diluent (in most cases water).
Formulations that are suitable for the effectiveness tests may be obtained in simple manner, for example~ according to the following prescriptions:
E X A M P L E 1:
Parts by weight of compound I ~calculated on the pure active ingredient) 16 parts by weight of compound IV as octanoate tcalculated on the pure active ingredient) 15.1 parts by weight of isotridecanol polyglycol ether (6 AEO) 10.1 parts by weight of cyclohexanone 29.0 parts by weight of xylene 6.5 parts by weight of a mixture of calcium dodecylbenzene-sulfonate and alkylphenyl-polyglycol ether ( ~ ATL,OX) 4.5 parts by weight of castor oil-polyglycol ether (40 AEO).
E X A M P L E 2:
22.0 Parts by weight of compound I (calculated on the pure active ingredient) 16.0 parts by weight of compound IV as octanoate (calculated on the pure active ingredient) :, -7_ ~.2~3~ZO
lOoO parts by weight of cyclohexanone 27O9 parts by weight of xylene 11.0 parts by weight of castor oil-polyglycol ether t~0 AEO) 9.0 parts by weight of a mixture of calcium dodecylbenzene-sulfonate and alkylphenyl-polyglycol ether ( ~ ATLOX).
The synergistic effect of the combinations of active substances becomes evident from the following Examples. Whereas the individual active ~` ingredients show some deficiencies in their herbicidal action, the combinations show a more extensive action on weeds which is more than a simple addition of effects.
A synergistic effect is present in those cases in which the action of the combinations of active substances is stronger than that of the active substances applied individually. The effect to be expected for a given combination of two herbicidal agents (cf. Colby~ S.R., "Calculation of synergistic and antagonistic ~esponses of herbicide combinations", Weeds I5 1967, pages 2Q to 22) can be calculated as follows:
If X represents the per cent of damage effected by herbicidal agent A with x kg/ha of amount applied and Y represents the per cent of damage effected by herbicidal agent B with y kg/ha of amount applied> the expected damage of the combination A + B with an amount applied of - -:. . . . ., - , : ,........... . ::: . . :
- .: - ~ :
,.
~v .
(x + y) kg~ha is calculated by way of the formula E = X + Y~
., ., ' . 100/
If the actual damage is greater than E, the effect of the combination is more than additive, i.e. a synergistic effect is produced, as has been demonstrated in the follow-ing Examples.
- E X A M P L E 3:
In a greenhouse test different weeds were treated after emergence with compounds I, III or IV as well as with the combinations I~III and I+IV. The result has been given in the following Table. The effect has gene~
rally been indicated in per cent of damage, and in the case of the combinations the results are shown both for the effect calculated in accordance with the above for-mula (in brackets) and subsequently for the effect ac-tually found.
- ~1.23ZZO
.
-` - 9 - HOE 77/F 244 ~ocs~ooo. L~ OO oo o~oo~
o o~ o o o .0 ~ o~ o r~ ) 1~
~D _~ ~ ,_ ~ ,_ ~
~ Ir~ N
O U~ ~ U~ ~ ~ 0 I ~ ~ 1 00 I . I . I . I . I .
=1' :3 0 0 Il~ O L~
'Cl~ ~ ~ CO cr~ 1~ I
_ _ _ _ _~ _ _ ~o~ooo Omu~o tno Lf~ O O~ O O O ~ r _~ ~_~ _~ _~
~ O ~ U~ ~
H ~ 1~ ~ N ~n I 1 00 1~ 1 . I . l l l l ~ OC> `D O O N ~ O
O L~ ~ ~
__ _~_ _ _ ~_ H .
H lS~ O Lr~ 0 0 0 O O O L~ O O
H C~l O t--C~ C~ O . ~ Lf~ c_ .- ~ .
a~
~ ~- ,~ ~_ .,~ . Ln L-~ 0 . ,_ S~ O C--~ ~, U~ 0 ~ I . . I . . I~ I . I .
~ ~ 0 0 oo ~ 0 S:: ~ CS~ O~ _`=t 11~ <~I
O _~_ __ _ _~ _ ~ _ D .
X O0 O~ O U~ O In ~ O ~O
O C~.l 0 ~O 1~ 0 0 N =r N Lf~ ,_ S~ ~ ~ ~ ~
O ~ Ll~
a~ ~ ~ L~
00 I .~ I . . l~ I . I .
1~3 ~0 ~ 0 N
nl N N U~ ~ 1 N
S __ __ _ _ _ Y
O O~ U~ O C~ U~ O ~ O Lt~ O ~ O ~ O ~
O . ~_ L~
.
~1 .,1 ~ O
~^ ~^
~1 0 ~ Q~
t~ 1 H H H ~ ~ ~ .C H H H ~ ~ ~: H H H H ~ ~
td C) H H H H H H 0 ~ H H H H ~--1 H H H H H H
~_S 6 ~t H H H 6 H H L H H t~--` H H
::S ~ t[~ O t~ 3 0~
b~ ~ O ~ + + + -~ E ~ ~ ~^
0~: ~ ~ td ~ ~I ~ ~
H O ~H HH H ~ C~ H H 0 H G~ O H H
C2. ~ ~C~. O H H 0 ~ :~
6~: rl O .~ ~1 ~~1~N =~ ~ ~ ~ l ~ Q) ~1 ~ ~1 O~
X6 0 ~ O~ In ~ 1~ ~ ~1 ~1 ~ O rt O O
b~ C~ C),, , . (~ 3 ' ' 1~ :~ .
O0 U~ ~_)--O O O O ~-- O O ~ O 'C~ O O
O ~ ~ ~ ~
E~ ~ ~ c~ ~
.
- : . ,~, ,, ' . , ' .' .: ' " ` . : ~ , -lU~ U
The comparison between the effect found and the calculated effect clearly shows the synergistic effectO
E X A M P L E 4:
.
In a compatibility test performed in the greenhouse with spring wheat and spring barley it could be proved that the treatment with the individual compounds as well as with the combined compounds did no harm to the crop plants mentioned above, k~/ha __ Preparation _ ~ _ g wheat _ Spring barley Q.72 I û 0 10 0.54 II o o 0.6 III 0 û
0.6 IV o o I +III ~0.72 kg/ha I + û.6 kg/ha III~ 0 û
I +IV ~0.72 kg/ha I + 0.6 kg/ha IV) û 0 II +III ~û.54 kg/ha II + 0.6 kg/ha III) 0 II ~IV (0.54 kg/ha II + 0.6 kg/ha IV) 0 0 . . . . -.,; ~ ;~
Claims (4)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Herbicidal compositions which contain as active ingredients a com-pound of the formula (A) in which X is chlorine or bromine, Y is hydrogen, if X is chlorine, or Y is chlorine if X is bro-mine, and Z is (C1 - C4) - alkyl, in combination with a compound of the formula (B) in which R is bromine or iodine, R1 is hydrogen, an alkali metal or ammonium cation or (C1 - C8) - alkanoyl, wherein the mixing ratio of (A) to (B) is in the range of from 1:0.05 to 1:5.
2. Herbicidal compositions as claimed in claim 1 which have a content of A I) 2- [ 4-(2'-chloro-4'-bromophenoxy)-phenoxy ]-propionic acid-methyl ester or II) 2-[ 4-(4'-chlorophenoxy)-phenoxy ]-propionic acid-isobutyl ester in combination with B III) 3,5-diiodo-4-hydroxybenzonitrile and/or its sodium, potassium or NH4 salts or its octanoate, or IV) 3,5-dibromo-4-hydroxybenzonitrile or its sodium salt or its octa-noate as active ingredients.
3. Herbicidal compositions as claimed in claims 1 and 2, wherein the mixing ratio of (A) to (B) is in the range of from 1:0.1 to 1:1.
4. A method of combating mono- and dicotyledonous weeds in cereal cul-tures, which comprises applying thereto from 0.5 to 2 kg/ha of the composition of either of claims 1 or 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772755617 DE2755617A1 (en) | 1977-12-14 | 1977-12-14 | HERBICIDAL MIXTURES |
| DEP2755617.8 | 1977-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123220A true CA1123220A (en) | 1982-05-11 |
Family
ID=6026062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA317,863A Expired CA1123220A (en) | 1977-12-14 | 1978-12-13 | Herbicidal compositions |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5489023A (en) |
| AT (1) | AT364192B (en) |
| AU (1) | AU525418B2 (en) |
| BE (1) | BE872765A (en) |
| CA (1) | CA1123220A (en) |
| CS (1) | CS203025B2 (en) |
| DD (1) | DD157750A5 (en) |
| DE (1) | DE2755617A1 (en) |
| DK (1) | DK545078A (en) |
| FR (1) | FR2411565A1 (en) |
| GB (1) | GB2011787B (en) |
| GR (1) | GR65232B (en) |
| IL (1) | IL56195A0 (en) |
| IT (1) | IT1101737B (en) |
| NL (1) | NL7812145A (en) |
| PL (1) | PL112150B1 (en) |
| PT (1) | PT68909A (en) |
| RO (1) | RO75105A (en) |
| SE (1) | SE7812782L (en) |
| SU (1) | SU884549A3 (en) |
| ZA (1) | ZA786972B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3415069A1 (en) * | 1983-11-19 | 1985-05-30 | Hoechst Ag, 6230 Frankfurt | HERBICIDAL AGENTS |
-
1977
- 1977-12-14 DE DE19772755617 patent/DE2755617A1/en not_active Withdrawn
-
1978
- 1978-11-22 DD DDAPA01N/209248A patent/DD157750A5/en unknown
- 1978-11-30 DK DK545078A patent/DK545078A/en not_active Application Discontinuation
- 1978-12-09 GR GR57833A patent/GR65232B/en unknown
- 1978-12-12 AT AT0882578A patent/AT364192B/en not_active IP Right Cessation
- 1978-12-12 RO RO7895883A patent/RO75105A/en unknown
- 1978-12-12 IT IT30757/78A patent/IT1101737B/en active
- 1978-12-12 SU SU782696353A patent/SU884549A3/en active
- 1978-12-12 IL IL56195A patent/IL56195A0/en unknown
- 1978-12-13 NL NL7812145A patent/NL7812145A/en not_active Application Discontinuation
- 1978-12-13 SE SE7812782A patent/SE7812782L/en unknown
- 1978-12-13 CA CA317,863A patent/CA1123220A/en not_active Expired
- 1978-12-13 JP JP15325578A patent/JPS5489023A/en active Pending
- 1978-12-13 ZA ZA00786972A patent/ZA786972B/en unknown
- 1978-12-13 AU AU42458/78A patent/AU525418B2/en not_active Expired
- 1978-12-13 GB GB7848278A patent/GB2011787B/en not_active Expired
- 1978-12-13 PT PT68909A patent/PT68909A/en unknown
- 1978-12-13 CS CS788287A patent/CS203025B2/en unknown
- 1978-12-14 BE BE192321A patent/BE872765A/en unknown
- 1978-12-14 PL PL1978211747A patent/PL112150B1/en unknown
- 1978-12-14 FR FR7835211A patent/FR2411565A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SU884549A3 (en) | 1981-11-23 |
| BE872765A (en) | 1979-06-14 |
| IL56195A0 (en) | 1979-03-12 |
| PT68909A (en) | 1979-01-01 |
| DE2755617A1 (en) | 1979-06-21 |
| DD157750A5 (en) | 1982-12-08 |
| JPS5489023A (en) | 1979-07-14 |
| IT7830757A0 (en) | 1978-12-12 |
| SE7812782L (en) | 1979-06-15 |
| IT1101737B (en) | 1985-10-07 |
| AU525418B2 (en) | 1982-11-04 |
| GR65232B (en) | 1980-07-30 |
| AU4245878A (en) | 1979-06-21 |
| FR2411565A1 (en) | 1979-07-13 |
| ZA786972B (en) | 1979-11-28 |
| GB2011787A (en) | 1979-07-18 |
| NL7812145A (en) | 1979-06-18 |
| AT364192B (en) | 1981-09-25 |
| CS203025B2 (en) | 1981-02-27 |
| DK545078A (en) | 1979-06-15 |
| PL211747A1 (en) | 1979-07-30 |
| RO75105A (en) | 1980-10-30 |
| GB2011787B (en) | 1982-05-12 |
| ATA882578A (en) | 1981-02-15 |
| PL112150B1 (en) | 1980-09-30 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |