CA1094842A - Wild oat herbicide - Google Patents
Wild oat herbicideInfo
- Publication number
- CA1094842A CA1094842A CA248,483A CA248483A CA1094842A CA 1094842 A CA1094842 A CA 1094842A CA 248483 A CA248483 A CA 248483A CA 1094842 A CA1094842 A CA 1094842A
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- CA
- Canada
- Prior art keywords
- wild oat
- cereal crops
- land
- tract
- comprises applying
- 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.)
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
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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)
- Plural Heterocyclic Compounds (AREA)
Abstract
A B S T R A C T
A herbicidal composition for controlling wild oats comprising an N,N-disubstituted alanine derivative and 3-isopropyl~lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide.
A herbicidal composition for controlling wild oats comprising an N,N-disubstituted alanine derivative and 3-isopropyl~lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide.
Description
This invention relates to a wild oat herbicide and to a method Or controlling wild oats in cereal crops.
Wild oat (Avena fatua) is a major world-wide weed problem and is becoming an increasing competitor to cereal grain crops. As a result the annual economiG
losses resulting from wild oat infestations are cor-siderable.
An established family of compounds which has shown a very high level of activity towards wild oat and also a marked selectivity towards cereals is the N,N-di-substituted alanine derivatives, for example SUFFIX- ~ -herbicide for use in wheat and BARNON-herbicide for use in barley.
The Applicant has found that by mixing one of these N,N-di-subs~ituted alanine derivatives with BENTAZON-herbicide (3-isopxopyl-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide) and employing the mixture as a wild oat herbicide, synergistic responses are obtained.
Accordingly, the invention provides a herbicidal composition, the active ingredients of which are:
(a) 3-isopropyl-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide (hereinafter referred to as the "dioxide) and (b) an N,N-di-substituted alanine derivative having the following general formula:
, . .
/ CX 4~
~/ ~ (I) ~ CH-COR
wherein Y and Z each individually represent chlorine or fluorine;
X represents oxygen or sulphur; and R represents a group of formula -ORl, in which Rl is hydrogen, a metal salt-forming or an optionally alkyl substituted ammonium ion, an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; ~:
a group of formula -SR2, in which R2 is an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; or a group of ormula NR~R4 or -ON=CR3R4, in which R3 and R4 each individually is hydrogen, hydroxy, an optionally substituted alkyl, alkenyl, aryl, alkaryl, heterocyclyl, alkoxy, alkylthio or amino ~ :
group, or R3 and R4 toge~her represent a polymethylene group optionally interrupted by one or more hetero atoms, the weight ratio of alanine derivative to dioxide, being in the range of from 1:0.2 to 1:25.
:
~ :
.~
- : -84~
l'he optional substituents in the alanine derivati~ie referred to above are preferably one or two chl~rine, fluorine, alkyl (1-4C), or alkoxy (1-4C) groups. The alkyl, alkenyl, alkoxy, alkylthio groups referred to in the above general formula suitably contain up to 6 carbon atoms, preferably up to 4 carbon atoms. The aryl, alkaryl, cycloalkyl, het;erocyclyl and polymethylene groups suitably contain up to 10 carbon atoms, preferably up to 7 carbon atoms. The hetero-atoms which may be in the polymethylene group or in the heterocyclyl group can be oxygen, nitrogen or sulphur atoms but are preferably one or two oxygen and/or nitrogem a!toms.
By far the best results have been obtained by mixing the dioxide with the 3-chloro-4-fluoro-alanine derivative, that is to say the compound of general formula I, wherein Z is fluorine and Y is chlorlne.
Examples of these N,N-di-substituted alanine derivatives and their methods of synthesis can be found in the following German patent specifications:
OLS 1,643,527 (P, 1375), OLS 2,109,910 (P. 1576);
OLS 2,302,029 (K 1267); OLS 2,349,970 (K 1280);
OLS 2,504,319 (K 1305); OLS 2,460,691 (K 1306) Especially preferred alanine derivatives are those having the following general formula:
-5~ 84~2 CH-COOR
y CH3 wherein Y represents chlorine, Z represents fluorine, and R is a hydrogen atom or an alkyl gro~p containing up to 6 carbon atoms3 e~g., methyl, ethyl or isopropyl.
Of these compounds one of the best wild oat herbicides for use in barley crops is the compound having the formula II above, wherein:
Z is fluorine;
Y - chlorine; and R = isopropyl.
One of the best compounds for use in wheat crops has the formula II above, wherein:
Z = fluorine;
Y = chlorine; and ~ R = methyl.
The alanine derivatives can exist in optically-active forms and,generally speaking, the laevo-rotatory lsomer is the most active ~orm and, thus, where it is appropriate, the alanine derivative may be employed in ltS most active optically-active form in the composition according to the invention.
8~Z
Testing at a number of dosage levels indicates that the composition according to the invention exhibits a synergistic level of herbicidal activity with respect to wild oats, This is particularly surprising as one of the c~mponents, the dioxide, has no recorded activity on wild oats. Furthermore, although the activity of the composition is increased with respect to wild oat, there is no sub-stantial increase in the effect of the composition upon cereal grains, so that it can be used safely as a selective herbicide in wild oat infested crops.
This invention makes it possible to control wild oat over a wide range of its development by post-emergent foliar applications. Wild oat can be controlled in cereal crops by application of from 0.25 to 2.0 kg/ha of the composition according to the invention wherein the weight ratio of the alanine derivative to the dioxide is in the range of from 1:0~2 to 1:25~ preferably in the range of from 1:0.5 to 1:15.
The herbicidal composition according to the invention may also employ a carrier, a surface-active agent or both a carrier and a surface-active agent to facilitate application of the composition to wild oat infested land at the desired dosage rates. The term "carrier" as used herein means a solid or fluid material, which may be in-organic or organic and of synthet.ic or natural origin.
:
8a.Z
,:;
Typical solid carriers include natural and synthetic clays and silicates, for example, natural silicas, such as diatomaceous earths and aluminium silicates, for example, kaolinites7 montmorillonites, and micas.
Typical fluid carriers are ketones, for example, methyl-cyclohexanone, aromatic hydrocarbons, for example, methyl-naphthalenes petroleum fractions, such as, for example, petroleum xylenes and light mineral oils, and chlorinated hydrocarbons, for example, carbon tetrachloride. Mixtures of liquids are often suitable.
One or more surface-active agents and/or stickers can be included in the formulation. The surface-active agent may be an emulsifying agent or a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating -herbicides or insecticides may be used. Examples of suitable surface-active agents are~the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the con-densation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol, condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example, p-oc-tylphenol or p-octylcresol, with eth~lene oxide and/or propylene oxide; sulphates or sulphonates of these condensation proaucts, alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example, sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates, such as sodium dodecylben~ene sulphonate; and polymers of ethylene oxide and copolymers o~ ethylene oxide and propylene oxide.
Aqueous dispersions and emulsions, for example, compositions obtained by diluting a wettable powder or a concentrate according to the inven-tion with water, also lie within the scope of the present invention.
The said emulsions may be of the water-in-oil or of the oil-in-water type, and may-have a thick "mayonnaise"-like consistency.
The inventlon also includes a method of selectively controlling wild oat in cereal crops which comprises applying the composition according to the invention to a tract of land which is bearing cereal crops and in-fested with wild oat.
The compositions of this invention can be applied to : the wild oat plants in a conventional manner. The dust and liquid compositions:may be conveniently applied by the use of power-dusters, boom and hand sprayers, and spray-~r ~9~8~2 duster. The compositions can also be applied from aeroplanes as a dust or spray because of the effectiveness of the compositions at low dosages.
If desired, the composition according to the invention may also be mixed with other wild oat herbicides, for example, 4-chloro-2-butynyl-_-chlorocarbanilate (common name: barban; available under the trade mark:
"Carbyne"), or methyl 2-chloro~3-t4-chlorophenyl)propionate ~common name:
chlorphenprop methyl; available under the trade mark: "Bidisin"), or 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulphate available under the trade mark "Avenge").
In order to obtain a broader spectrum of activity, especially against broad-leaf weeds, the composition according to the invention may be mixed with compatible herbicides which have a herbicidal action upon broad-leaf weeds but are selective in their action with respect to cereal crops. Examples of such selective broad-leaf herbicides are phenoxyalkanoic acid derivatives of the general formula:
X' Y' ~\ ~ A-R' wherein X' represents a chlorine atom or a methyl group; Y' represents a chlorine atom; Z' represents a hydrogen or chlorine atom; A represents an alkylene group of 1-4 ,, "
carbon atoms; and R' represents a carboxyl group, together with the salts and esters thereof. Particular examples are:
Wild oat (Avena fatua) is a major world-wide weed problem and is becoming an increasing competitor to cereal grain crops. As a result the annual economiG
losses resulting from wild oat infestations are cor-siderable.
An established family of compounds which has shown a very high level of activity towards wild oat and also a marked selectivity towards cereals is the N,N-di-substituted alanine derivatives, for example SUFFIX- ~ -herbicide for use in wheat and BARNON-herbicide for use in barley.
The Applicant has found that by mixing one of these N,N-di-subs~ituted alanine derivatives with BENTAZON-herbicide (3-isopxopyl-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide) and employing the mixture as a wild oat herbicide, synergistic responses are obtained.
Accordingly, the invention provides a herbicidal composition, the active ingredients of which are:
(a) 3-isopropyl-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide (hereinafter referred to as the "dioxide) and (b) an N,N-di-substituted alanine derivative having the following general formula:
, . .
/ CX 4~
~/ ~ (I) ~ CH-COR
wherein Y and Z each individually represent chlorine or fluorine;
X represents oxygen or sulphur; and R represents a group of formula -ORl, in which Rl is hydrogen, a metal salt-forming or an optionally alkyl substituted ammonium ion, an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; ~:
a group of formula -SR2, in which R2 is an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; or a group of ormula NR~R4 or -ON=CR3R4, in which R3 and R4 each individually is hydrogen, hydroxy, an optionally substituted alkyl, alkenyl, aryl, alkaryl, heterocyclyl, alkoxy, alkylthio or amino ~ :
group, or R3 and R4 toge~her represent a polymethylene group optionally interrupted by one or more hetero atoms, the weight ratio of alanine derivative to dioxide, being in the range of from 1:0.2 to 1:25.
:
~ :
.~
- : -84~
l'he optional substituents in the alanine derivati~ie referred to above are preferably one or two chl~rine, fluorine, alkyl (1-4C), or alkoxy (1-4C) groups. The alkyl, alkenyl, alkoxy, alkylthio groups referred to in the above general formula suitably contain up to 6 carbon atoms, preferably up to 4 carbon atoms. The aryl, alkaryl, cycloalkyl, het;erocyclyl and polymethylene groups suitably contain up to 10 carbon atoms, preferably up to 7 carbon atoms. The hetero-atoms which may be in the polymethylene group or in the heterocyclyl group can be oxygen, nitrogen or sulphur atoms but are preferably one or two oxygen and/or nitrogem a!toms.
By far the best results have been obtained by mixing the dioxide with the 3-chloro-4-fluoro-alanine derivative, that is to say the compound of general formula I, wherein Z is fluorine and Y is chlorlne.
Examples of these N,N-di-substituted alanine derivatives and their methods of synthesis can be found in the following German patent specifications:
OLS 1,643,527 (P, 1375), OLS 2,109,910 (P. 1576);
OLS 2,302,029 (K 1267); OLS 2,349,970 (K 1280);
OLS 2,504,319 (K 1305); OLS 2,460,691 (K 1306) Especially preferred alanine derivatives are those having the following general formula:
-5~ 84~2 CH-COOR
y CH3 wherein Y represents chlorine, Z represents fluorine, and R is a hydrogen atom or an alkyl gro~p containing up to 6 carbon atoms3 e~g., methyl, ethyl or isopropyl.
Of these compounds one of the best wild oat herbicides for use in barley crops is the compound having the formula II above, wherein:
Z is fluorine;
Y - chlorine; and R = isopropyl.
One of the best compounds for use in wheat crops has the formula II above, wherein:
Z = fluorine;
Y = chlorine; and ~ R = methyl.
The alanine derivatives can exist in optically-active forms and,generally speaking, the laevo-rotatory lsomer is the most active ~orm and, thus, where it is appropriate, the alanine derivative may be employed in ltS most active optically-active form in the composition according to the invention.
8~Z
Testing at a number of dosage levels indicates that the composition according to the invention exhibits a synergistic level of herbicidal activity with respect to wild oats, This is particularly surprising as one of the c~mponents, the dioxide, has no recorded activity on wild oats. Furthermore, although the activity of the composition is increased with respect to wild oat, there is no sub-stantial increase in the effect of the composition upon cereal grains, so that it can be used safely as a selective herbicide in wild oat infested crops.
This invention makes it possible to control wild oat over a wide range of its development by post-emergent foliar applications. Wild oat can be controlled in cereal crops by application of from 0.25 to 2.0 kg/ha of the composition according to the invention wherein the weight ratio of the alanine derivative to the dioxide is in the range of from 1:0~2 to 1:25~ preferably in the range of from 1:0.5 to 1:15.
The herbicidal composition according to the invention may also employ a carrier, a surface-active agent or both a carrier and a surface-active agent to facilitate application of the composition to wild oat infested land at the desired dosage rates. The term "carrier" as used herein means a solid or fluid material, which may be in-organic or organic and of synthet.ic or natural origin.
:
8a.Z
,:;
Typical solid carriers include natural and synthetic clays and silicates, for example, natural silicas, such as diatomaceous earths and aluminium silicates, for example, kaolinites7 montmorillonites, and micas.
Typical fluid carriers are ketones, for example, methyl-cyclohexanone, aromatic hydrocarbons, for example, methyl-naphthalenes petroleum fractions, such as, for example, petroleum xylenes and light mineral oils, and chlorinated hydrocarbons, for example, carbon tetrachloride. Mixtures of liquids are often suitable.
One or more surface-active agents and/or stickers can be included in the formulation. The surface-active agent may be an emulsifying agent or a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating -herbicides or insecticides may be used. Examples of suitable surface-active agents are~the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the con-densation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol, condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example, p-oc-tylphenol or p-octylcresol, with eth~lene oxide and/or propylene oxide; sulphates or sulphonates of these condensation proaucts, alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example, sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates, such as sodium dodecylben~ene sulphonate; and polymers of ethylene oxide and copolymers o~ ethylene oxide and propylene oxide.
Aqueous dispersions and emulsions, for example, compositions obtained by diluting a wettable powder or a concentrate according to the inven-tion with water, also lie within the scope of the present invention.
The said emulsions may be of the water-in-oil or of the oil-in-water type, and may-have a thick "mayonnaise"-like consistency.
The inventlon also includes a method of selectively controlling wild oat in cereal crops which comprises applying the composition according to the invention to a tract of land which is bearing cereal crops and in-fested with wild oat.
The compositions of this invention can be applied to : the wild oat plants in a conventional manner. The dust and liquid compositions:may be conveniently applied by the use of power-dusters, boom and hand sprayers, and spray-~r ~9~8~2 duster. The compositions can also be applied from aeroplanes as a dust or spray because of the effectiveness of the compositions at low dosages.
If desired, the composition according to the invention may also be mixed with other wild oat herbicides, for example, 4-chloro-2-butynyl-_-chlorocarbanilate (common name: barban; available under the trade mark:
"Carbyne"), or methyl 2-chloro~3-t4-chlorophenyl)propionate ~common name:
chlorphenprop methyl; available under the trade mark: "Bidisin"), or 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulphate available under the trade mark "Avenge").
In order to obtain a broader spectrum of activity, especially against broad-leaf weeds, the composition according to the invention may be mixed with compatible herbicides which have a herbicidal action upon broad-leaf weeds but are selective in their action with respect to cereal crops. Examples of such selective broad-leaf herbicides are phenoxyalkanoic acid derivatives of the general formula:
X' Y' ~\ ~ A-R' wherein X' represents a chlorine atom or a methyl group; Y' represents a chlorine atom; Z' represents a hydrogen or chlorine atom; A represents an alkylene group of 1-4 ,, "
carbon atoms; and R' represents a carboxyl group, together with the salts and esters thereof. Particular examples are:
2,4-dichlorophenoxy-acetic acid;
( )-2-(2,4-dichlorophenoxy)propionic acid;
4-chloro-2-methylphenoxy acetic acid;
(+)-2-(4-cllloro-2-me-thylphenoxy)propionic acid, and 4-(4-chloro-2-methylphenoxy)-butyric acid.
The invention is further illustrated by the following Examples in which to show the effect of the compositions according to the invent;on on wild oats (Avena fatua) in cereal crops, cultivated oats (Avena sativa) were used.
It has been found from the Applicant's experience in this field that data obtained from tests on cultivated oats is entirely representative of the effect on wild oats and in many respects is more reliable in that the results are reproducible.
EXAMPLE I
The mixture under test in this Example was as follows:
(A) The dioxide as a 48% emulaiflable concentrate sold commercially as BASAGRA~* herbicide, and (B) isopropyl ~-benzoyl-~-(3-chloro-4-fluorophenyl)-2-aminopropionate as a 20% emulsifiable concentrate sold commercially as BAR~ON herbicide.
*Trademark - 10 -, ~ .... .. . . ...
1094~
A number of 7 cm pots o~ John Innes No. 1 compost were sown with 25-30 seeds of wheat, and a number with cultivated oat (Avena sativa). When the plants had reached the 1-1~ leaf stage, a solution of the mixture under test was sprayed, using a logarithmic dilution sprayer, at five different doses for each species.
Mixtures of different proportions of the compounds were also sprayed at five doses each.
Assessments were made 11 days after spraying.
Phytotoxicity to the barley and oat plants was assessed visually (barley on a standard 0-9 scale and oat on a percentage scale were 100 = no growth after spraying).
Th~se values expressed as perce~tages of the rules for untreated barley and the untreated oats were analysed ~ -by computer to calculate the growth inhibition dosages to give a 50% reduction for barley and a 90% reduction for oat abbreviated to GID50 barley, and GIDgo oat respectively. The selectivity factor (S.F.) for the compound under test can be calculated using the following 20 ~ expression:
S.F. = GI 90 oat The selectivity factor prov1des a comparative measure of the selective herbicidal effect of the mixturesor ~compounds ~der test, the larger the selectivity factor~
.
; : . - ... :. ' `
the better the selectivity effect between the two plant species.
The range of mixtures used and the results obtained are shown in Table I.
TABLE I
.
RatioGID (kg/ha) GID O (kg/ha) Selectivity (B):(A)5for (B) 9 for (B)factor 0:1 Barley Oat~ID,o b~
1:4 2.12 0.12 18 1:2 2.~8 0.09 28 1:1 2.81 0.10 28 1:0.5 3.69 O.Og 41 .1:0 ~ 6~ _ _ 0.1~ 26 The results indica-te that the dioxide (Compound A) by itself has no effect on oats and yet in combination with the alanine derivative (Compound B) the GID90 oat values are less than that obtained for Compound B aloneO This establishes that the A ingredient is acting in some way which produces a synergistic result. Moreover, it will be seen that the selectivity factor is on the whole improved rather than adversely affected.
X
.
~4~34Z
E ~iPLE II
The mixture under test in this Example was as follows:
(A) The dioxide as a 48% emulsifiable concentrate sold commercially as BASAGRAN herbicide, and (C) methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate as a 15% emulsifiable concentrate.
The test procedure of Example I was followed except that wheat seeds were used instead of barley seeds. The results are shown in the following Table II.
TABLE II
: _ _ _ _ Ratio GID1o (kg/ha) GIDgO (kg/ha) Selectivity (C):(A) for (C) for (C) factor _ _ GID wild oat ~ ~-Wheat Oat 9 0:1 _ _ 1: & 1 .00 0.09 11 , . -1:4 0.72 0.07 10 1:2 1.01 0.06 17 ~ 1:1 0.84 0.07 12 ~ ~
:: ~ ~:o o.o8_~ ~ 8 _ ~ :
, .~
.. .. . .
( )-2-(2,4-dichlorophenoxy)propionic acid;
4-chloro-2-methylphenoxy acetic acid;
(+)-2-(4-cllloro-2-me-thylphenoxy)propionic acid, and 4-(4-chloro-2-methylphenoxy)-butyric acid.
The invention is further illustrated by the following Examples in which to show the effect of the compositions according to the invent;on on wild oats (Avena fatua) in cereal crops, cultivated oats (Avena sativa) were used.
It has been found from the Applicant's experience in this field that data obtained from tests on cultivated oats is entirely representative of the effect on wild oats and in many respects is more reliable in that the results are reproducible.
EXAMPLE I
The mixture under test in this Example was as follows:
(A) The dioxide as a 48% emulaiflable concentrate sold commercially as BASAGRA~* herbicide, and (B) isopropyl ~-benzoyl-~-(3-chloro-4-fluorophenyl)-2-aminopropionate as a 20% emulsifiable concentrate sold commercially as BAR~ON herbicide.
*Trademark - 10 -, ~ .... .. . . ...
1094~
A number of 7 cm pots o~ John Innes No. 1 compost were sown with 25-30 seeds of wheat, and a number with cultivated oat (Avena sativa). When the plants had reached the 1-1~ leaf stage, a solution of the mixture under test was sprayed, using a logarithmic dilution sprayer, at five different doses for each species.
Mixtures of different proportions of the compounds were also sprayed at five doses each.
Assessments were made 11 days after spraying.
Phytotoxicity to the barley and oat plants was assessed visually (barley on a standard 0-9 scale and oat on a percentage scale were 100 = no growth after spraying).
Th~se values expressed as perce~tages of the rules for untreated barley and the untreated oats were analysed ~ -by computer to calculate the growth inhibition dosages to give a 50% reduction for barley and a 90% reduction for oat abbreviated to GID50 barley, and GIDgo oat respectively. The selectivity factor (S.F.) for the compound under test can be calculated using the following 20 ~ expression:
S.F. = GI 90 oat The selectivity factor prov1des a comparative measure of the selective herbicidal effect of the mixturesor ~compounds ~der test, the larger the selectivity factor~
.
; : . - ... :. ' `
the better the selectivity effect between the two plant species.
The range of mixtures used and the results obtained are shown in Table I.
TABLE I
.
RatioGID (kg/ha) GID O (kg/ha) Selectivity (B):(A)5for (B) 9 for (B)factor 0:1 Barley Oat~ID,o b~
1:4 2.12 0.12 18 1:2 2.~8 0.09 28 1:1 2.81 0.10 28 1:0.5 3.69 O.Og 41 .1:0 ~ 6~ _ _ 0.1~ 26 The results indica-te that the dioxide (Compound A) by itself has no effect on oats and yet in combination with the alanine derivative (Compound B) the GID90 oat values are less than that obtained for Compound B aloneO This establishes that the A ingredient is acting in some way which produces a synergistic result. Moreover, it will be seen that the selectivity factor is on the whole improved rather than adversely affected.
X
.
~4~34Z
E ~iPLE II
The mixture under test in this Example was as follows:
(A) The dioxide as a 48% emulsifiable concentrate sold commercially as BASAGRAN herbicide, and (C) methyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate as a 15% emulsifiable concentrate.
The test procedure of Example I was followed except that wheat seeds were used instead of barley seeds. The results are shown in the following Table II.
TABLE II
: _ _ _ _ Ratio GID1o (kg/ha) GIDgO (kg/ha) Selectivity (C):(A) for (C) for (C) factor _ _ GID wild oat ~ ~-Wheat Oat 9 0:1 _ _ 1: & 1 .00 0.09 11 , . -1:4 0.72 0.07 10 1:2 1.01 0.06 17 ~ 1:1 0.84 0.07 12 ~ ~
:: ~ ~:o o.o8_~ ~ 8 _ ~ :
, .~
.. .. . .
Claims (17)
1. A herbicidal composition the active ingredients of which are:
(a) 3-isopropyi-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide (hereinafter referred to as the "dioxide");
and (b) an N,N-disubstituted alanine derivative having the following general formula:
(I) wherein Y and Z each individually represent chlorine or fluorine;
X represents oxygen or sulphur, and R represents a group of formula -OR1, in which R1 is hydrogen, a metal salt-forming or an optionally alkyl-substituted ammonium ion, an optionally substituted alkyl,cycloalkyl, aryl, alkenyl or alkaryl group;
a group of formula -SR2, in which R2 is an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; or a group of formula -NR3R4 or -ON=CR3R4, in which R3 and R4 each individually is hydrogen, hydroxy, an optionally substituted alkyl, alkenyl, aryl, alkaryl, heterocyclyl, alkoxy, alkylthio or amino group, or R3 and R4 together represent a polymethylene group optional-ly interrrupted by one or more hetero atoms, the weight ratio of alanine derivative to dioxide being in the range of from 1:0.2 to 1:25.
(a) 3-isopropyi-lH-2,1,3-benzthiadiazin-(4),3H-one-2,2-dioxide (hereinafter referred to as the "dioxide");
and (b) an N,N-disubstituted alanine derivative having the following general formula:
(I) wherein Y and Z each individually represent chlorine or fluorine;
X represents oxygen or sulphur, and R represents a group of formula -OR1, in which R1 is hydrogen, a metal salt-forming or an optionally alkyl-substituted ammonium ion, an optionally substituted alkyl,cycloalkyl, aryl, alkenyl or alkaryl group;
a group of formula -SR2, in which R2 is an optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkaryl group; or a group of formula -NR3R4 or -ON=CR3R4, in which R3 and R4 each individually is hydrogen, hydroxy, an optionally substituted alkyl, alkenyl, aryl, alkaryl, heterocyclyl, alkoxy, alkylthio or amino group, or R3 and R4 together represent a polymethylene group optional-ly interrrupted by one or more hetero atoms, the weight ratio of alanine derivative to dioxide being in the range of from 1:0.2 to 1:25.
2. A herbicidal composition according to claim 1, wherein for the general formula of ingredient (b) Z is fluorine and Y is chlorine.
3. A herbicidal composition according to claim 1 wherein the N,N-disubstituted alanine derivative has the following general formula:
(II) wherein Y represents chlorine, Z represents fluorine, and R is a hydrogen atom or an alkyl group containing up to 6 carbon atoms.
(II) wherein Y represents chlorine, Z represents fluorine, and R is a hydrogen atom or an alkyl group containing up to 6 carbon atoms.
4. A herbicidal composition according to claim 3, wherein ingredient (b) is the compound of formula II, wherein Z is fluorine, Y is chlorine and R is isopropyl.
5. A herbicidal composition according to claim 3, wherein ingredient (b) is the compound of formula II, wherein Z is fluorine, Y is chlorine and R is methyl.
6. A herbicidal composition according to claim 1 wherein in general formula I X is sulfur.
7. A herbicidal composition according to claim 1 wherein in general formula I X is sulfur, Y is chlorine and Z is fluorine.
8. A herbicidal composition according to claim 1 wherein in general formula I X is sulfur, Y is chlorine, Z is fluorine and R represents a group of formula -OR1 in which R1 is a hydrogen atom or an alkyl group containing up to 6 carbon atoms.
9. A method of selectively controlling wild oat in cereal crops which comprises applying at a rate effective to control selectively wild oat a composition as claimed in claim 1, 2 or 3 to a tract of land which is bear-ing cereal crops and infested with wild oat.
10. A method of selectively controlling wild oat in cereal crops which comprises applying as a post-emergent foliar treatment at a rate effective to control selectively wild oat a composition as claimed in claim 1, 2 or 3 to a tract of land which is bearing cereal crops and infested with wild oat.
11. A method of selectively controlling wild oat in cereal crops which comprises applying at a rate of 0.25 to 2.0 kg/ha a composition as claimed in claim 1, 2 or 3 to a tract of land which is bearing cereal crops and is infested with wild oat.
12. A method of selectively controlling wild oat in cereal crops which comprises applying at a rate effective to control selectively wild oat a composition as claimed in claim 4 or 5 to a tract of land which is bearing cereal crops and infested with wild oat.
13. A method of selectively controlling wild oat in cereal crops which comprises applying as a post-emergent foliar treatment at a rate effective to control selectively wild oat a composition as claimed in claim 4 or 5 to a tract of land which is bearing cereal crops and infested with wild oat.
14. A method of selectively controlling wild oat in cereal crops which comprises applying at a rate of 0.25 to 2.0 kg/ha a composition as claimed in claim 4 or 5 to a tract of land which is bearing cereal crops and is infested with wild oat.
15. A method of selectively controlling wild oat in cereal crops which method comprises applying at a rate effective to control selectively wild oat a composition as claimed in claim 6, 7 or 8 to a tract of land which is bearing cereal crops and is infested with wild oat.
16. A method of selectively controlling wild oat in cereal crops which comprises applying at a rate of 0.25 to 2.0 kg/ha a composition as claimed in claim 6, 7 or 8 to a tract of land which is bearing cereal crops and is in-fested with wild oat.
17. A method of selectively controlling wild oat in cereal crops which comprises applying as a post-emergent follar treatment at a rate to control selectively wild oat a composition as claimed in claim 6, 7 or 8 to a tract of land which is bearing cereal crops and infested with wild oat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17998/75 | 1975-04-30 | ||
| GB17998/75A GB1546375A (en) | 1975-04-30 | 1975-04-30 | Wild oat herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094842A true CA1094842A (en) | 1981-02-03 |
Family
ID=10104859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,483A Expired CA1094842A (en) | 1975-04-30 | 1976-03-22 | Wild oat herbicide |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS51130533A (en) |
| AU (1) | AU500148B2 (en) |
| BE (1) | BE841109A (en) |
| CA (1) | CA1094842A (en) |
| CH (1) | CH620097A5 (en) |
| CS (1) | CS191303B2 (en) |
| DD (1) | DD124459A5 (en) |
| DE (1) | DE2618664A1 (en) |
| DK (1) | DK190976A (en) |
| FI (1) | FI761177A (en) |
| FR (1) | FR2309141A1 (en) |
| GB (1) | GB1546375A (en) |
| GR (1) | GR60445B (en) |
| HU (1) | HU178732B (en) |
| IT (1) | IT1063221B (en) |
| NL (1) | NL7604514A (en) |
| PL (1) | PL103511B1 (en) |
| PT (1) | PT65048B (en) |
| SE (1) | SE430017B (en) |
| SU (1) | SU651641A3 (en) |
| ZA (1) | ZA762539B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2333414A1 (en) * | 1973-06-30 | 1975-01-16 | Basf Ag | HERBICIDE |
| DE2336444A1 (en) * | 1973-07-18 | 1975-02-06 | Basf Ag | HERBICIDE |
-
1975
- 1975-04-30 GB GB17998/75A patent/GB1546375A/en not_active Expired
-
1976
- 1976-03-22 CA CA248,483A patent/CA1094842A/en not_active Expired
- 1976-04-26 BE BE1007343A patent/BE841109A/en unknown
- 1976-04-26 IT IT22669/76A patent/IT1063221B/en active
- 1976-04-28 SE SE7604919A patent/SE430017B/en unknown
- 1976-04-28 GR GR50609A patent/GR60445B/en unknown
- 1976-04-28 JP JP51047965A patent/JPS51130533A/en active Pending
- 1976-04-28 PT PT65048A patent/PT65048B/en unknown
- 1976-04-28 PL PL1976189126A patent/PL103511B1/en unknown
- 1976-04-28 SU SU762354748A patent/SU651641A3/en active
- 1976-04-28 NL NL7604514A patent/NL7604514A/en not_active Application Discontinuation
- 1976-04-28 CS CS762792A patent/CS191303B2/en unknown
- 1976-04-28 FI FI761177A patent/FI761177A/fi not_active Application Discontinuation
- 1976-04-28 CH CH533776A patent/CH620097A5/en not_active IP Right Cessation
- 1976-04-28 FR FR7612563A patent/FR2309141A1/en active Granted
- 1976-04-28 DD DD192569A patent/DD124459A5/xx unknown
- 1976-04-28 DE DE19762618664 patent/DE2618664A1/en not_active Withdrawn
- 1976-04-28 ZA ZA762539A patent/ZA762539B/en unknown
- 1976-04-28 DK DK190976A patent/DK190976A/en not_active Application Discontinuation
- 1976-04-28 AU AU13426/76A patent/AU500148B2/en not_active Expired
- 1976-04-29 HU HU76SE1830A patent/HU178732B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI761177A (en) | 1976-10-31 |
| ZA762539B (en) | 1977-04-27 |
| CS191303B2 (en) | 1979-06-29 |
| AU500148B2 (en) | 1979-05-10 |
| IT1063221B (en) | 1985-02-11 |
| DK190976A (en) | 1976-10-31 |
| GB1546375A (en) | 1979-05-23 |
| CH620097A5 (en) | 1980-11-14 |
| JPS51130533A (en) | 1976-11-12 |
| GR60445B (en) | 1978-06-01 |
| SE430017B (en) | 1983-10-17 |
| FR2309141A1 (en) | 1976-11-26 |
| BE841109A (en) | 1976-10-26 |
| AU1342676A (en) | 1977-11-03 |
| SU651641A3 (en) | 1979-03-05 |
| PL103511B1 (en) | 1979-06-30 |
| DE2618664A1 (en) | 1976-11-11 |
| PT65048B (en) | 1977-09-12 |
| NL7604514A (en) | 1976-11-02 |
| PT65048A (en) | 1976-05-01 |
| FR2309141B1 (en) | 1979-04-20 |
| HU178732B (en) | 1982-06-28 |
| SE7604919L (en) | 1976-10-31 |
| DD124459A5 (en) | 1977-02-23 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |