GB1593167A - Herbicidal mixtures and compsitioms - Google Patents
Herbicidal mixtures and compsitioms Download PDFInfo
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- GB1593167A GB1593167A GB52433/77A GB5243377A GB1593167A GB 1593167 A GB1593167 A GB 1593167A GB 52433/77 A GB52433/77 A GB 52433/77A GB 5243377 A GB5243377 A GB 5243377A GB 1593167 A GB1593167 A GB 1593167A
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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Description
(54) HERBICIDAL MIXTURES AND COMPOSITIONS
(71) We, HOECHST AKTIENGESELLSCHAFT, a body corporate organised according to the laws of the Federal Republic of Germany, of 6230
Frankfurt/Main 80, Postfach 80 03 20, Federal Republic of Germany, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to herbicidally active mixtures and to compositions containing them.
It is known that a number of chlorine- and trifluoro-methyl-substituted 4phenoxyphenoxy-a-propionic acid esters exhibit a specific effect against economically important weed grasses, for example annual blackgrass, wild oats, barnyard grass, large crabgrass, bristle grass, ryegrass and couch grass (cf. German
Offenlegungsschrift Nos. 2,223,894 and 2,433,067). 2-Chloro-4-bromo-substituted 4-phenoxyphenoxy-a-propionic acid esters have also been proposed for the same purpose (cf. German Offenlegungsschrift No. 2,601,548). Compounds of this type (hereinafter referred to as type 1)) can be used not only in sugar beet, leguminosae, vegetables and other dicotyledonous crop plants, but partly also in barley, wheat and rye, preferably by spraying after emergence of the plants.
It is also known that many herbicidally active substances have a good effect against dicotyledonous weeds, but no or very little effect against weed grasses.
Compounds of this type (hereinafter referred to as type (2)) comprise, inter alia,
Desmedipham and Phenmedipham (cf. 3rd Symposium on novel herbicides, Paris
1969), N-(3-chloro-4-ethoxyphenyl)-N',N'-dimethyl urea (cf. German offenlegungsschrift No. 2,221,795), Methabenzthiazuron (cf. Biol. Bundensanstalt fir Land- und Forstwirtschaft, Pflanzenschutzmittelverzeichnis 1975/76, Page
105), and Metamitron (cf. Zeitschrift für Pflanzenkrankheiten und Pflanzenschutz, SH VII, 1975, pages 367-374).
The present invention is based on the surprising observation that the combined
application of certain compounds of types (1) and (2) produces a more than additive, i.e. synergistic, effect on the control of weed grasses.
The present invention therefore provides mixtures comprising
(I) a 2 - [4 - (4' - chlorophenoxy) - phenoxy] - propionic acid lower alkyl
ester (I), or
a 2 - [4 - (2',4' - dichlorophenoxy) - phenoxy] - propionic acid lower
alkyl ester (II), or
a 2 - [4 - (2' - chloro - 4' - bromophenoxy) - phenoxy] - propionic acid
lower alkyl ester (III), or
a 2 - [4 - (4' - trifluoromethylphenoxy) - phenoxy] - propionic acid
lower alkyl ester (1V), (2) 3 - ethoxycarbonylaminophenyl N - phenylcarbamate (Desmedipham;
A) or
3 - methoxycarbonylaminophenyl N - (3' - methylphenyl) - carbamate
(Phenmedipham; B), or
N - 3 - chloro - 4 - ethoxyphenyl - N',N' - dimethylurea (C), or
N - (2 - benzthiazolyl) - N,N' - dimethylurea (Methabenzthiazuron; D)
or
3 - methyl - 4 - amino - 6 - phenyl - 1,2,4 - triazin - 5(4H) - one (Metamitron; E), but excluding mixtures of I or II and B or E and of IV and C or D.
The term 'lower alkyl' is used herein to mean an alkyl group having from 1 to 4
carbon atoms.
The present invention also provides herbicidal compositions comprising such a
mixture as active ingredient, together with a carrier, and a method for combating
undesired plant growth which comprises applying such a composition to the area
containing the undesired plant growth.
The isobutyl ester of I and the methylesters of ll, III and IV are preferred as
type (1) compounds. The ratio of the amounts of compounds of type (1) to type (2)
can vary within wide limits between about 1:0.5 and 1:17. The preferred ratio in
each case depends on the particular compounds in the mixture, the weeds to be
combated and their development stage. Mixtures of compounds I, II or III and A
or of III and B are preferably in a ratio of from 1:1 to 1:4, whereas mixtures of IV
and A or IV and B are preferably in a ratio of from 1:0.5 to 1:2. Mixtures of
compounds I, II or III with compounds C or D are preferably in a ratio of from 1:2
to 1:6, and mixtures of III or IV with E are preferably in a ratio of from 1:6 to 1:14.
The herbicidal compositions according to the present invention can be in the form of wettable powders, emulsifiable concentrates or dusts and may contain the usual formulation auxiliaries, for example wetting agents, dispersing agents, solid
or liquid inert substances and grinding auxiliaries or solvents.
Suitable solid carrier materials are mineral substances such as aluminium
silicates, aluminium oxides, kaolin, chalks, siliceous chalks, talc, kieselguhr, or
hydrated silicic acids or combinations of such mineral substances with special
additives, for example chalk treated with sodium stearate. As carrier material for
liquid formulations all usual and suitable organic solvents can be used, for example toluene, xylene, diacetone alcohol, isophorone, gasolines, paraffin oils, dioxane,
dimethylformamide, dimethylsulfoxide, ethyl acetate, butyl acetate,
tetrahydrofuran and chlorobenzene.
As additives there can be used glue-like cellulose products or polyvinyl
alcohols.
Suitable wetting agents are appropriate emulsifiers such as oxethylated
alkylphenols, salts of aryl or alkylaryl sulfonic acids, salts of ethoxylated beiizenesulfonic acids and 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 hydrated silicic
acids or kieselguhr.
Suitable grinding auxiliaries are inorganic or organic salts such as sodium
sulfate, ammonium sulfate, sodium carbonate, sodium bicarbonate, sodium
thiosulfate, sodium stearate, and sodium acetate.
In general, the herbicidal mixtures according to the present invention are
contained in the compositions in amounts of from 2 to 75 /n Optionally, the
compositions may also contain other known active ingredients.
The amounts to be applied in practice vary within wide limits. Compositions
containing mixtures of 1, II or III and A and of III and B are used suitably in a total
amount of from 0.5 to 5, preferably 1 to 3 kg of mixture per hectare, compositions
containing mixtures of IV and A and of IV and B are suitably used in an amount of
from 0.1 to 5 and preferably 1 to 3 kg of mixture per hectare, compositions containing mixtures of 1,11 or III and C or D are suitably used in an amount of from 0. I to 10, preferably 0.5 to 5 kg of mixture per hectare and compositions containing mixtures of III or IV and E are suitably used in an amount of from 1 to 15 and
preferably 5 to 10 kg of mixture per hectare.
The following formulation Examples illustrate the invention. The biological
Examples illustrate the herbicidal properties of the compositions of the invention.
FORMULATION EXAMPLE 1
25.0 Parts by weight of compound II (methyl ester) are liquefied at 600C and
absorbed on
18.7 parts by weight of synthetic silicic acid (mixture 1)
Separately, a mixture of
26.2 parts by weight of compound A
8.0 parts by weight of sodium dinaphthylmethane - disulfonate
2.1 parts by weight of partially saponified polyvinyl acetate
3.0 parts by weight of sodium alkylnaphthalene - sulfonate
5.0 parts by weight of sodium bicarbonate and
9.0 parts by weight of synthetic silicic acid is prepared and finely ground on a pin mill (mixture 2). Next, mixtures I and 2 are blended together and ground again on a slowly running cross beater mill to obtain the wettable powder ready for use.
Ratio of A to II=1.05:1.
FORMULATION EXAMPLE 2
26.2 Pads by weight of compound A
19.0 parts by weight of diatomaceous earth
8.0 parts by weight of sodium dinaphthylmethane - disulfonate
2.0 parts by weight of sodium alkylnaphthalene - sulfonate
0.5 part by weight of sodium dodecylbenzenesulfonate and
6.6 parts by weight of sodium bicarbonate are mixed and finely ground at high speed in a pin mill (mixture 1).
At 60"C 20.0 parts by weight of compound III (methyl ester) are liquefied and
adsorbed on
15.1 parts by weight of synthetic silicic acid (mixture 2).
Both mixtures are ground together in a slowly rotating cross beater mill to give a wettable powder.
Ratio of A to III=1.31:1.
FORMULATION EXAMPLE 3
A mixture 1 is prepared as described in Example 2 from
26.2 parts by weight of compound B
19.0 parts by weight of keiselguhr
12.0 parts by weight of sodium lignin - sulfate
4.0 parts by weight of sodium alkylnaphthalene - sulfonate and
1.1 parts by weight of partially saponified polyvinyl acetate.
A mixture 2 is prepared as described in Example 2 from 20.0 parts by weight of compound III as methyl ester and 15.1 parts by weight of synthetic silicic acid and both mixtures are ground together in a cross beater mill.
Ratio of B to III=1.31:1.
FORMULATION EXAMPLE 4
30.0 Parts by weight of compound B
8.0 parts by weight of sodium dinaphthylmethanedisulfonate
1.0 part by weight of dioctylsulfosuccinic acid ester in the form of its sodium salt
2.0 parts by weight of sodium oleyl - N - methyltauride
0.5 part by weight of sodium palmitate
5.0 parts by weight of sodium bicarbonate
15.0 parts by weight of synthetic silicic acid and
3.5 parts by weight of diatomaceous earth are mixed and finely ground at high speed in a pin mill (mixture 1). 18 Parts by weight of the methyl ester of compound IV are liquefied at 600C and adsorbed in a high speed mixer on 14 parts of synthetic silicic acid (mixture 2). Mixtures 1 and 2 are then blended together and ground in a slowly rotating cross beater mill to give a wettable powder ready for use.
Ratio of B to IV=1.67:1.
FORMULATION EXAMPLE 5
12.0 Parts by weight of compound I as its isobutyl ester are liquefied at 600C
and absorbed on
8.5 parts by weight of synthetic silicic acid (mixture 1).
Separately, a mixture is prepared from
39.0 parts by weight of compound C
13.0 parts by weight of sodium - lignin - sulfonate
3.0 parts by weight of sodium dibutylnaphthalenesulfonate
2.0 parts by weight of partially saponified polyvinyl acetate
1.0 part by weight of polypropylene glycol and
16.6 parts by weight of synthetic silicic acid and finely ground on a pin mill (mixture 2). Mixture I and mixture 2 are then blended together and ground again on a slowly rotating cross beater mill to give a wettable powder ready for use.
Ratio of C to I=3.25:1.
FORMULATION EXAMPLE 6
As described in Example 5, two mixtures are prepared separately and then ground together to give a wettable powder.
Mixture I
18.0 parts by weight of compound II as its methyl ester
15.0 parts by weight of synthetic silicic acid
Mixture 2
35.0 parts by weight of compound C
14.0 parts by weight of sodium lignin - sulfonate
3.2 parts by weight of sodium oleyl - N - methyltauride
1.0 part by weight of sodium palmitate
11.0 parts by weight of synthetic silicic acid.
Ratio of C to II=1.94:1.
FORMULATION EXAMPLE 7
In the manner described in Example 5, two mixtures are prepared separately and then ground together to give a wettable powder.
Mixture 1
15.7 Parts by weight of the methyl ester of compound III
12.3 parts by weight of synthetic silicic acid
Mixture 2
36.4 Parts by weight of compound C
14.6 parts by weight of sodium lignin - sulfonate
2.0 parts by weight of sodium oleyl - N - methyltauride
2.0 parts by weight of dioctylsulfosuccinic acid ester in the form of its sodium salt
2.0 parts by weight of sodium oleyl - N - methyltauride
5.0 parts by weight of sodium bicarbonate and
10.0 parts by weight of synthetic silicic acid.
Ratio of C to III=2.4:1.
FORMULATION EXAMPLE 8
8.0 Parts by weight of the isobutyl ester of compound I are liquefied at 600C
and absorbed on
5.7 parts by weight of synthetic silicic acid (mixture 1).
Separately,
41.5 parts by weight of compound D
14.0 parts by weight of sodium lignin - sulfinate
4.0 parts by weight of sodium dibutylnaphthalenesulfonate
1.0 part by weight of sodium dodecylbenzenesulfonate and
20.8 parts by weight of diatomaceous earth are mixed and finely ground on a pin mill (mixture 2). Then, mixtures 1 and 2 are blended together and ground once again on a slowly rotating cross beater mill to give a wettable powder ready for use.
Ratio of D to I=5.19:1.
FORMULATION EXAMPLES 9 to 12
In similar manner formulations can be prepared from the constituents indicated in the following table.
TABLE 9)1 isobutyl 10) II methyl 11)111 methyl 12) III methyl
ester ester ester ester
Constituents parts by weight
Mixture 1
active compound 12.0 18.0 8.0 15.0 synthetic silicic acid 8.5 15.0 5.67 12.3
Mixture 2 compound D 39.0 35.0 41.5 36.4 sodium dinaphthylmetharie disulfonate 9.0 8.0 10.0 sodium lignin-sulfonate 5.0 - 15.0 sodium oleyl-N-methyltaurate 3.0 - - 0.5 sodium dibutylnaphthalenesulfonate - 3.0 - 3.0 sodium alkylnaphthalenesulfonate - - 5.0 sodium dodecylsulfate - - 1.0 0 0.s partially saponified polyvinyl - 1.0 acetate synthetic silicic acid 18.6 15.0 18.5 18.0 ratio D:I= D:II= D:III= D:III=
3.25:1 1.94:1 5.19:1 2.43:1
BIOLOGICAL EXAMPLES
EXAMPLE 1
Plants of annual blackgrass and sugar beet were grown in pots in the
greenhouse and treated in the three to four leaf stage with aqueous emulsions of
compound I as its isobutyl ester and compound A, respectively, and with
compositions of the said components in different proportions. The result 4 weeks
after treatment is indicated in the following Table 1. It can be seen that compound
I alone had a good effect on annual blackgrass, whereas compound A did not show
any effect. With the compositions the effect on annual blackgrass was surprisingly
much higher, above all with doses of A+I of 1.0+0.12 and 1.0+0.06 kg per hectare.
Sugar beet was not damaged.
TABLE 1
Effect in post-emergence trial (greenhouse test)
dose effect ( /" damage on
treated with kg/ha blackgrass sugar beet
A 1.0 0 0
I (as isobutyl ester) 0.5 100 0
0.25 97.5
0.12 85
0.06 65
A+I 1.0+0.5 100 0
1.0+0.25 100 1.0+0.12 97.5
1.0+0.06 75
EXAMPLE 2
In a similar test, active comounds II and A alone and in combination were examined as to their effect on wild oats and sugar beet.
In this case, too, the composition showed a drastical and unexpected increase in the effect on wild oat.
TABLE 2
Effect of herbicidal combinations in a post-emergence trial (greenhouse test)
dose effect (OXo damage) on
treated with (kg/ha) wild oats sugar beet
A 1.0 0 0
II (as ethyl ester) 1.0 98.7 0
0.5 97.5
0.25 80
0.12 65.6
0.06 4.1
A+II 1.0+1.0 100 0
1.0+0.5 99.5
1.0+0.25 95 1.0+0.12 92.5
1.0+0.06 76.2
EXAMPLE 3
In an open air trial in a field infested with various types of weeds the active
compounds of the preceding example were sprayed after emergence individually
and in combination, partly as a tank mixture and partly as formulated wettable
powder. The result, 5 weeks after the treatment, as indicated in the following Table
3 shows that
A alone was effective only against dicotyledonous weeds (curled blackgrass
and chickweed)
II alone was effective exclusively against wild oats.
The combinations of A+II had a distinctly better effect on wild oats than
compound II alone, especially with a dose of 0.72 kg/ha of compound II.
In all trials sugar beet was left unharmed.
TABLE 3
Effect of herbicidal compositions in a post-emergence trial (field test)
effect (% damage) on
dose curled blacktreated with (kg/ha) wild oats grass chickweed sugar beet
A 0.94 0 95 100 0 II (asmethylester) 0.9 92.5 0 0 0
0.72 75 0 0 0
A+II* 0.94+0.9 97.5 97.5 100 0
0.94+0.72 95.0 95 100 0
A+II** 0.94+0.9 98.75 97.5 100 0
0.75+0.72 96.25 92.5 100 0
*as tank mixture
**as wettable powder formulated according to Formulation Example 1.
EXAMPLE 4
In a manner analogous to that described in Example 2, compounds iII, A and
B alone and combinations of A+III and B+III were sprayed on wild oats and sugar
beet. In this case, too, the combinations had a distinctly better effect on the wild
oats than the individual compounds.
TABLE 4
Effect of herbicidal combinations in a post-emergence trial (greenhouse test)
dose effect (% damage) on
treated with (kg/ha) wild oats sugar beet
A 0.94 0 0
B 0.94 0 0
III 0.72 98.7 0
0.36 90
0.18 75
0.09 32.5
A+III 0.94+0.72 100 0 0.94+0.36 99.2 0*94+0.18 90
0.94+0.09 80
B+III 0.94+0.72 100 0
0.94+0.36 99.2
0.94+0.18 97.5
0.94+0.09 85
EXAMPLE 5
In a trial in pots under natural climatic conditions the compounds as used in the preceding example were sprayed on wild oats and annual blackgrass individually and in combination. This test confirmed the synergistic effect of the combinations on wild oats. The effect on annual blackgrass was likewise increased
distinctly as compared to the exclusive use of compound III although compounds
A and B were ineffective.
TABLE 5
Effect of herbicidal combinations in a post-emergence trial (vegetation hall)
dose effect (% damage) on
(kg/ha) wild oats annual treated with blackgrass
A 0.94 0 0
B 0.94 0 0
III 0.72 92.5 85
0.54 67.5 65
A+III* 0.94+0.72 99.4 92.5
0.70+0.54 87.5 85
B+III** 0.94+0.72 97.5 93.7
0.70+0.54 90.0 92.5
*as tank mixture
**as wettable powder formulated according to Formulation Example 3.
EXAMPLE 6
In a greenhouse test compounds A, B and IV alone and combinations of A+IV
and B+IV were sprayed after emergence on the weed grasses wild oats and annual
blackgrass and the crop plant sugar beet. The combinations were diluted in dilution
series in a constant mixing ratio of 1.74 to 1.
The results indicated in Table 6 confirm that the combinations had a distinctly
better effect on the weed grasses than compound IV alone although compounds A
and B when applied individually, were ineffective on grasses.
TABLE 6
Effect of herbicidal combinations in a post-emergence
trial in the greenhouse
effect (% damage) on
dose annual treated with (kg/ha) wild oats blackgrass sugar beet
B 0.470 0 0 0
A 0.470 0 0 0
IV (as methyl ester) 0.270 100 100 0
0.135 88.3 98.8 0
0.067 48.5 92.5 0
0.034 16.1 70 0
B+IV 0.470+0.270 100 100 0
0.235+0.135 100 100 0
0.117+0.067 80 100 0
0.059+0.034 77.5 97.8 0
A+IV 0.470+0.270 100 100 0
0.235+0.135 100 100 0
0.117+0.067 89.5 98.3 0
0.059+0.034 48.8 91.3 0
EXAMPLE 7
In a field infested with couch grass various plots were treated, after emergence of sugar beet, with compounds B and IV individually and with combinations thereof according to the invention. The results in Table 7 show that 4 weeks after the treatment the combinations had a better effect against couch grass than compound IV alone although compound B alone was absolutely ineffective. 10
Weeks after the treatment, the differences were still distinctly perceptible. In the plots treated with compound IV the effect had slightly subsided, while in the areas treated with combinations of B with IV the effect was even more pronounced.
TABLE 7
Effect of herbicidal combinations in a post-emergence trial (field test)
dose effect ( /n damage) on treated with (kg/ha) couch grass sugar beet
4* 10* 4* 10*
B 0.94 0 0 0 0
IV 1.80 90 85 0 0
1.44 87.5 77.5 0 0
B+IV 0.94+1.80 97.5 99 0 0 0.94+1.44 95 97.5 0 0
*weeks after treatment
EXAMPLE 8
Seeds of barley, wheat and several weed grasses were sown in pots and placed in the greenhouse. After the development or about 3 leaves, the plants were sprayed with compounds C and I, respectively, and with mixtures thereof.
The result 4 weeks after treatment is indicated in the following Table 8. The figures show that 0.62 kg/ha of compound C alone had an unsatisfactory effect against 2 of the three types of weeds used, but that in combination together with 0.31 kg/ha of compound I the effect was almost complete against all weeds although compound I was effective against annual blackgrass only. Surprisingly, the effect of the combination against bent and cleaver was better than expected.
The combination of 1.25 kg per hectare of C+0.31 kg per hectare of I also showed an increased effect, but with the effect of C alone being already so good, a synergism could not be clearly ascertained.
The mixing ratio of C to I was 4:1 and 2:1, respectively.
TABLE 8
Effect of herbicidal combinations in the post-emergence trial (greenhouse test) in V of damage with doses in kg/ha
C I C 0.62+ types of plants 0.62 0.31 10.31 a) weeds
bent 90 0 100
cleaver 75 0 95
blackgrass 32.5 85 95 b) crop plants
wheat 0 0 0
barley 0 0 0
EXAMPLE 9
In a greenhouse test compounds C, II and III were sprayed alone and in form of the combinations C+II and C+III on 4 types of weeds and on barley and wheat.
In the combinations the ratio of the active compound was 1.91:1 and 2.44:1, respectively. The combinations exhibited an unexpectedly distinct increase in the effect against all types of weeds.
TABLE 9
Effect of herbicidal combinations in a post-emergence trial in the greenhouse in V of damage
dose wild black barnyard barley compound (kg/ha) oat grass bent grass wheat
C 0.44 38 48.5 92.5 90 0
0.22 0 8 32 51 0
II 0.23 91 70 0 0 0
0.11 90 16 0 0 0
III 0.18 92.5 90 16 0 0
0.08 82.5 82.5 0 0 0
C+II 0.44+0.23 99 5 100 99.5 97.5 0
0.22+0.11 97.5 75 80 75 0
C+III 0.44+0.18 100 99.5 97.5 98.7 0
0.22+0.09 95 90 90 90 0 EXAMPLE 10
Seeds of annual blackgrass (Alopecurus myosuroides) were sown in pots and after emergence in the 2 to 3-leaf stage the plants were treated in the greenhouse with compounds D and I alone and with combinations thereof in a mixing proportion of D to I of 5.19:1 and 3.25:1, respectively.
The result of the treatment, expressed as percentage of damage 4 weeks after the treatment, is indicated in Table 10. It can be seen that with the combinations,
above all in low doses, the effect against annual blackgrass was unexpected
increased as compared with the effect obtained with the individual compounds. In no case wheat was damaged (not indicated in the table).
TABLE 10
Ratio of D:I=5.19: 1 Ratio of D:I=3.25: 1
active dose active dose
compound (kg/ha) effect compound (kg/ha) effect
I 0.270 95 I 0.270 95
0.135 75 0.135 75
0.067 32 0.067 32
0.034 16 0.034 16
D 1.4 80 D 0.875 70
0.7 65 0.437 48.5
0.35 32 0.219 0
0.175 0 0.109 0
I+D 0.270+1.4 100 I+D 0.270+0.875 99
0.135+0.7 90 0.135+0.437 95
0.067+0.35 85 0.067+0.219 70
0.034+0.175 65 0.024+0.109 60
EXAMPLE 11
In a further test in the greenhouse active compounds D, II and III were applied alone and in combinations of D+II and D+III after emergence of the plants. In the combinations the ratios were as follows:
D+II=1.75+0.9 kg/ha, corresponding to 1.94:1
D+III=1.75+0.72 kg/ha, corresponding to 2.43:1.
At the time of treatment the weed grasses, annual blackgrass and bent, had approximately 3 leaves while the crop plants, spring wheat and spring barley, had developed 3 to 4 leaves.
The results indicated in Table 11 show that compound D had a weak effect on annual blackgrass and a good effect on bent, while compounds II and III, both used as their methyl esters, had a relatively good effect on blackgrass but not on bent.
The combinations are characterized by an unexpectedly high effect on
blackgrass and on bent. Wheat and barley were damaged only with the highest doses, the damage was similar to that caused by compound D alone.
TABLE 11
Effect of herbicidal combinations in a post emergence trial (greenhouse).
effect (V damage) on
active dose compound (kg/ha) grass blackbent wheat barley
D 0.88 62 96 7.5 10
0.44 8 48.5 0 1.2
0.22 0 8 0 0
II 0.45 87.5 0 0 0
0.23 70 0 0 0
0.11 16.2 0 0 0
III 0.36 92.5 32.5 0 0
0.18 87.5 16.2 0 0
0.09 75 0 0 0
D+II 0.88+0.45 95 97.5 10 12.5
0.44+0.23 87.5 85 2.5 2.5
0.22+0.11 48.5 32.5 0 0
D+III 0.88+0.36 100 97.5 7.5 10
0.44+0.18 97.5 90 0 1.2
0.22+0.09 90 32.5 0 0
EXAMPLE 12
In a field test in sugar beet infested with wild oats and some types of dicotyledonous weeds active compounds E, III and IV alone and combinations of
E+III and E+IV were sprayed after emergence of the beet plants. E showed no
effect against wild oats and had a weak effect only on dicotyledonous weeds. The effect of III and IV on wild oats was also relatively weak. Surprisingly, with the combinations the effect on wild oats and on the dicotyledonous weeds common orache, wild mustard and knotgrass increased beyond the expected degree.
TABLE 12
Effect of herbicidal combinations in a post-emergence trial (field test)
effect ( /O damage) on
active dose wild common wild knot- sugar
compound (kg/ha) oats orache mustard grass beet
E 4.9 0 30 57.5 32.5 0
III 0.72 62 0 0 0 0
IV 0.36 43 0 0 0 0
0.54 60 0 16 0 0
E+III 4.9+0.72 97.5 60 75 50 0
E+IV 4.9+0.36 82.5 57.5 70 45 0
4.9+0.54 92.5 60 72.5 55 0
WHAT WE CLAIM IS:
1. A mixture comprising
(1) a 2-[4-(4'-chlorophenoxy)-phenoxy]-propionic acid lower alkyl ester (I),
or
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (6)
1. A mixture comprising
(1) a 2-[4-(4'-chlorophenoxy)-phenoxy]-propionic acid lower alkyl ester (I),
or
a 2-[4-(2',4'-dichlorophenoxy)-phenoxy]-propionie acid lower alkyl ester (if), or
a 2-[4-(2'-chloro-4'-bromophenoxy)-phenoxy]-propionic acid lower alkyl
ester (III), or
a 2-[4-(4'-trifluoromethylphenoxy)-phenoxy]-propionic acid lower alkyl
ester (IV) and
(2) 3-ethoxycarbonylaminophenyl N-phenylcarbamate (A) or
3-methoxycarbonylaminophenyl N-(3'-methylphenyl)-carbamate (B), or N-3-ehloro-4-ethoxyphenyl-N',N'-dimethylurea (C), or
N-(2-benzthiazolyl)-N,N'-dimethylurea (D), or 3-methyl-4-amino-6-phenyl- 1 ,2,4-triazin-5(4H)-one (E) with the exception of I or II and B or E, and IV and C or D.
2. A mixture as claimed in claim 1, wherein the weight ratio of component (1) to component (2) is from 1:0.5 to 1:17.
3. A mixture as claimed in claim 1 or claim 2, wherein component (1) is the isobutyl ester of compound I or the methyl ester of compound II, III or IV.
4. A herbicidal composition comprising as active ingredient a mixture as claimed in any one of claims I to 3, together with a carrier.
5. A herbicidal composition substantially as described in any one formulation Examples 1 to 12 herein.
6. A method for combating undesired plant growth which comprises applying to an area containing the undesired plant growth a herbicidal composition as claimed in claim 4 or claim 5.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762657583 DE2657583A1 (en) | 1976-12-18 | 1976-12-18 | HERBICIDAL COMBINATIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1593167A true GB1593167A (en) | 1981-07-15 |
Family
ID=5995941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52433/77A Expired GB1593167A (en) | 1976-12-18 | 1977-12-16 | Herbicidal mixtures and compsitioms |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5379031A (en) |
| AT (1) | AT362183B (en) |
| BE (1) | BE862011A (en) |
| BG (5) | BG28685A4 (en) |
| CA (1) | CA1099126A (en) |
| CS (1) | CS207493B2 (en) |
| DD (1) | DD134473A5 (en) |
| DE (1) | DE2657583A1 (en) |
| DK (1) | DK563077A (en) |
| ES (1) | ES464973A1 (en) |
| FR (3) | FR2379251A1 (en) |
| GB (1) | GB1593167A (en) |
| GR (1) | GR74888B (en) |
| IL (1) | IL53631A (en) |
| IT (1) | IT1088569B (en) |
| NL (1) | NL7713780A (en) |
| NZ (1) | NZ185999A (en) |
| PL (2) | PL110328B1 (en) |
| SE (1) | SE7714306L (en) |
| TR (1) | TR20230A (en) |
| ZA (1) | ZA777484B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2122901A (en) * | 1982-05-21 | 1984-01-25 | Sandoz Ltd | Synergistic herbicidal mixture |
| GB2190293A (en) * | 1986-05-10 | 1987-11-18 | J D Campbell & Sons Limited | Herbicidal composition |
| US5012017A (en) * | 1988-08-18 | 1991-04-30 | Dowelanco | Phenoxyphenoxypropionates, intermediates thereof and methods of preparation |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5551005A (en) * | 1978-10-12 | 1980-04-14 | Kumiai Chem Ind Co Ltd | Herbicidal composition |
| US4309210A (en) * | 1978-12-01 | 1982-01-05 | Ciba-Geigy Corporation | Preemergence method of selectively controlling weeds in crops of cereals and composition therefor |
| DE3202440A1 (en) * | 1982-01-26 | 1983-07-28 | Bayer Ag, 5090 Leverkusen | HERBICIDES CONTAINING METHABENZTHIAZURON IN COMBINATION WITH PARTICULAR PHENOXYPROPIONIC ACID ESTERS |
| DE3205103A1 (en) * | 1982-02-12 | 1983-08-18 | Bayer Ag, 5090 Leverkusen | HERBICIDAL CONTAINING METAMITRON IN COMBINATION WITH PARTICULAR PHENOXYPROPIONIC ACID ESTERS |
| DE3406655A1 (en) * | 1984-02-24 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | HERBICIDES CONTAINING METHABENZTHIAZURON IN COMBINATION WITH PARTICULAR PYRIDINYLOXYACETIC ACID DERIVATIVES |
| DE3919036A1 (en) * | 1989-06-10 | 1990-12-13 | Hoechst Ag | LIQUID HERBICIDAL MIXTURE |
-
1976
- 1976-12-18 DE DE19762657583 patent/DE2657583A1/en not_active Withdrawn
-
1977
- 1977-12-12 ES ES464973A patent/ES464973A1/en not_active Expired
- 1977-12-13 BG BG7739615A patent/BG28685A4/en unknown
- 1977-12-13 BG BG7839616A patent/BG28686A4/en unknown
- 1977-12-13 NL NL7713780A patent/NL7713780A/en not_active Application Discontinuation
- 1977-12-13 TR TR20230A patent/TR20230A/en unknown
- 1977-12-13 BG BG038024A patent/BG28547A3/en unknown
- 1977-12-15 SE SE7714306A patent/SE7714306L/en unknown
- 1977-12-15 AT AT896277A patent/AT362183B/en not_active IP Right Cessation
- 1977-12-15 ZA ZA00777484A patent/ZA777484B/en unknown
- 1977-12-16 IT IT30868/77A patent/IT1088569B/en active
- 1977-12-16 CS CS778472A patent/CS207493B2/en unknown
- 1977-12-16 DD DD77202716A patent/DD134473A5/en unknown
- 1977-12-16 JP JP15072477A patent/JPS5379031A/en active Pending
- 1977-12-16 CA CA293,189A patent/CA1099126A/en not_active Expired
- 1977-12-16 GB GB52433/77A patent/GB1593167A/en not_active Expired
- 1977-12-16 DK DK563077A patent/DK563077A/en unknown
- 1977-12-16 NZ NZ185999A patent/NZ185999A/en unknown
- 1977-12-17 PL PL1977213543A patent/PL110328B1/en unknown
- 1977-12-17 PL PL1977203087A patent/PL106093B1/en unknown
- 1977-12-18 IL IL53631A patent/IL53631A/en unknown
- 1977-12-19 FR FR7738214A patent/FR2379251A1/en not_active Withdrawn
- 1977-12-19 BE BE183586A patent/BE862011A/en unknown
-
1978
- 1978-04-19 FR FR7811511A patent/FR2379254A1/en not_active Withdrawn
- 1978-04-19 FR FR7811510A patent/FR2379253A1/en active Pending
- 1978-12-13 BG BG039616A patent/BG28686A3/en unknown
- 1978-12-13 BG BG039615A patent/BG28685A3/en unknown
-
1981
- 1981-04-22 GR GR55004A patent/GR74888B/el unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2122901A (en) * | 1982-05-21 | 1984-01-25 | Sandoz Ltd | Synergistic herbicidal mixture |
| GB2190293A (en) * | 1986-05-10 | 1987-11-18 | J D Campbell & Sons Limited | Herbicidal composition |
| GB2190293B (en) * | 1986-05-10 | 1990-12-19 | J D Campbell & Sons Limited | Herbicidal compositions containing phenoxy alkanoic esters |
| US5012017A (en) * | 1988-08-18 | 1991-04-30 | Dowelanco | Phenoxyphenoxypropionates, intermediates thereof and methods of preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| BG28547A3 (en) | 1980-05-15 |
| ATA896277A (en) | 1980-09-15 |
| DK563077A (en) | 1978-06-19 |
| AT362183B (en) | 1981-04-27 |
| IT1088569B (en) | 1985-06-10 |
| PL110328B1 (en) | 1980-07-31 |
| BG28685A4 (en) | 1980-06-16 |
| ZA777484B (en) | 1978-10-25 |
| GR74888B (en) | 1984-07-12 |
| PL203087A1 (en) | 1978-07-17 |
| FR2379251A1 (en) | 1978-09-01 |
| TR20230A (en) | 1980-11-04 |
| CS207493B2 (en) | 1981-07-31 |
| BG28685A3 (en) | 1980-06-16 |
| IL53631A (en) | 1981-01-30 |
| JPS5379031A (en) | 1978-07-13 |
| IL53631A0 (en) | 1978-03-10 |
| ES464973A1 (en) | 1979-01-16 |
| DD134473A5 (en) | 1979-03-07 |
| FR2379253A1 (en) | 1978-09-01 |
| BE862011A (en) | 1978-06-19 |
| BG28686A3 (en) | 1980-06-16 |
| BG28686A4 (en) | 1980-06-16 |
| CA1099126A (en) | 1981-04-14 |
| DE2657583A1 (en) | 1978-06-22 |
| FR2379254A1 (en) | 1978-09-01 |
| SE7714306L (en) | 1978-06-19 |
| NZ185999A (en) | 1979-11-01 |
| NL7713780A (en) | 1978-06-20 |
| PL106093B1 (en) | 1979-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |