CA1202311A - Method of protecting cultivations of agrarian interest from the action of non selective herbicides - Google Patents
Method of protecting cultivations of agrarian interest from the action of non selective herbicidesInfo
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- CA1202311A CA1202311A CA000477061A CA477061A CA1202311A CA 1202311 A CA1202311 A CA 1202311A CA 000477061 A CA000477061 A CA 000477061A CA 477061 A CA477061 A CA 477061A CA 1202311 A CA1202311 A CA 1202311A
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- carboxylic acid
- dichloroacetyl
- thiazolidine
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- seeds
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Abstract
ABSTRACT OF THE DISCLOSURE
A method of protecting useful cultivations from the toxic action of non-selective herbicides, comprising using, as antidotes, a compound selected from N-dichloroacetyl-2-thiazoli-dine-carboxylic acid and the methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid. The present invention also provides as novel compounds a compound selected from N-dichloro-acetyl-2-thiazolidine-carboxylic acid and the methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid.
A method of protecting useful cultivations from the toxic action of non-selective herbicides, comprising using, as antidotes, a compound selected from N-dichloroacetyl-2-thiazoli-dine-carboxylic acid and the methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid. The present invention also provides as novel compounds a compound selected from N-dichloro-acetyl-2-thiazolidine-carboxylic acid and the methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid.
Description
3~
The present invention rela-tes to compounds useful as antidotes against the treatmen-t of plants with herbicides and to -their use an-tidotes.
This application is a divisional applica-tion of copend-ing~application No. ~23,89~ Eiled March :L8, 1983.
Ilerbicides belonging -to the class of chloroacetanilides or of thiolcarbamates are very useful compounds agains-t the weeds infes-ting agrarian cultivations.
Many of these herbicides, however, also exert their 10 toxic action towards cer-tain useful cul-tivations such as, for example, maize and sorghum, and, in consequence, being non-selective, -they cannot be used for weed-killing in such culitva-tions.
The availabi:Lity of antidotes, i.e. oE compouncls whjc~l pro-tect the usefu:L cultivations from the action of the herbicides without contemporaneously reducing their herbicide action towards the infes-ting plan-ts, also allows use of these herbicides for defending those useful cultivations which otherwise would be damaged.
Among the main herbicides which prove -to be phyto-toxic for cer-tain useful cultivations -there are those belonying to the class of the chloroace-tanilides comprising, for example, N-methox~me-thyl-2, 6-die-thyl~chloroacetanilide tCommon name:
Alachlor). N-butoxymethyl-2, 6-die-thyl-chloroacetanylide (common name: Butachlor), N-methoxyethyl-2-methyl-6-allyl-chloro-acetanilide and the ones belonging to the class of the thiol-carbama-tes comprising, e.g., N,N-diiaopropyl-S-(2, 3-dichloro-allyl)-thiolcarbamate (common name: Dialla-te); N,N-diisopropyl-S-(2,3,3-trichloroallyl)-thiolcarbamate (common name: Triallate);
N,N-diethyl-S-(4-chlorobenzyl)-thiolcarbamate (common name:
Benthiocarb); N,N-dipropyl-S-etllyl-thiolcarbamate (common name:
Eptam).
Compounds belonging to dif~erent chemical classes are known which are capable of protecting useful cultivations from the toxic action exerted by the herbicides.
For example, dichloroacetamides useful as antidotes have been described in U.S. Patent NoO ~,021,22~ (Stauffer) or in U.S. Paten-t No. ~,228,101 (Monteclison S~poA~ ) ~ 2-chloro-thiazoles disubstituted in positions ~, 5, which are useful as antidotes in the defence of sorghum cul-tivations have been described in European Patent application No. 27019 (Monsanto Co.)O
h~
~ pplicants have now found that the -toxic action oE non-selec~ive herbicides, belonging e.g. to the class of the chloroacetanilides and of the thiolcarbamates, towards useful cultivations can be signiEicantly reduced or elimina-ted, without decreasing, at the same time, the herbicide action towards in-festing plants if use is made, as antido-tes, of compounds of formula:
/ ____.
N - COOR (I) ~1 where:in: group COOR is in position 2 or ~ in the thiazolidine ring, r~ represents a hydrogerl atom or an alkyl Cl-C4; Rl repre-sents a hydrogen atom,or an acetyl group optionally subs-tituted by 1 to 3 halogen atoms.
~'~ h~C~/~
Thus, the inven-tion disclosed and claimed in copending~J
application No. 423,89~, is a method of reducing the damage~ to-wards useful cultiva-tions caused by non-selec-tive herbicides 20 belonging, for example, to -the class of the chloroacetanilides or of the thlolcarbamates, such method comprising treat:Lng the seeds, the plants or the soll in which they grow with arl eEfec-tive amount of an antido-te of formula I, ei-ther as such or in -the form of a sui-table composi-tion.
The invention of the copending; application also discloses and claims compositions containing a compound of formula I as an ac-tive ingredien-t along with inert vehicles and optionally other additives useful -to trea-t the seeds of useful plan-ts, the plan-ts themselves or -the soil in which -they grow.
The appLicationalso discloses and claims see~s o.E useful plants treated with an effective amount of a compound of formula The compounds of formul.a I may also be in the form of sa~ts, e.g. hyrochlorides, when in formu:La :t 1~1=11.
For the uses according to the invention of the copend-ing applica-tion, -the individual compounds oi~ formula I, also in admix-ture with one ano-ther, and the corresponding sal-ts are equally valid.
Some of the compounds of formula I are known, namely:
The present invention rela-tes to compounds useful as antidotes against the treatmen-t of plants with herbicides and to -their use an-tidotes.
This application is a divisional applica-tion of copend-ing~application No. ~23,89~ Eiled March :L8, 1983.
Ilerbicides belonging -to the class of chloroacetanilides or of thiolcarbamates are very useful compounds agains-t the weeds infes-ting agrarian cultivations.
Many of these herbicides, however, also exert their 10 toxic action towards cer-tain useful cul-tivations such as, for example, maize and sorghum, and, in consequence, being non-selective, -they cannot be used for weed-killing in such culitva-tions.
The availabi:Lity of antidotes, i.e. oE compouncls whjc~l pro-tect the usefu:L cultivations from the action of the herbicides without contemporaneously reducing their herbicide action towards the infes-ting plan-ts, also allows use of these herbicides for defending those useful cultivations which otherwise would be damaged.
Among the main herbicides which prove -to be phyto-toxic for cer-tain useful cultivations -there are those belonying to the class of the chloroace-tanilides comprising, for example, N-methox~me-thyl-2, 6-die-thyl~chloroacetanilide tCommon name:
Alachlor). N-butoxymethyl-2, 6-die-thyl-chloroacetanylide (common name: Butachlor), N-methoxyethyl-2-methyl-6-allyl-chloro-acetanilide and the ones belonging to the class of the thiol-carbama-tes comprising, e.g., N,N-diiaopropyl-S-(2, 3-dichloro-allyl)-thiolcarbamate (common name: Dialla-te); N,N-diisopropyl-S-(2,3,3-trichloroallyl)-thiolcarbamate (common name: Triallate);
N,N-diethyl-S-(4-chlorobenzyl)-thiolcarbamate (common name:
Benthiocarb); N,N-dipropyl-S-etllyl-thiolcarbamate (common name:
Eptam).
Compounds belonging to dif~erent chemical classes are known which are capable of protecting useful cultivations from the toxic action exerted by the herbicides.
For example, dichloroacetamides useful as antidotes have been described in U.S. Patent NoO ~,021,22~ (Stauffer) or in U.S. Paten-t No. ~,228,101 (Monteclison S~poA~ ) ~ 2-chloro-thiazoles disubstituted in positions ~, 5, which are useful as antidotes in the defence of sorghum cul-tivations have been described in European Patent application No. 27019 (Monsanto Co.)O
h~
~ pplicants have now found that the -toxic action oE non-selec~ive herbicides, belonging e.g. to the class of the chloroacetanilides and of the thiolcarbamates, towards useful cultivations can be signiEicantly reduced or elimina-ted, without decreasing, at the same time, the herbicide action towards in-festing plants if use is made, as antido-tes, of compounds of formula:
/ ____.
N - COOR (I) ~1 where:in: group COOR is in position 2 or ~ in the thiazolidine ring, r~ represents a hydrogerl atom or an alkyl Cl-C4; Rl repre-sents a hydrogen atom,or an acetyl group optionally subs-tituted by 1 to 3 halogen atoms.
~'~ h~C~/~
Thus, the inven-tion disclosed and claimed in copending~J
application No. 423,89~, is a method of reducing the damage~ to-wards useful cultiva-tions caused by non-selec-tive herbicides 20 belonging, for example, to -the class of the chloroacetanilides or of the thlolcarbamates, such method comprising treat:Lng the seeds, the plants or the soll in which they grow with arl eEfec-tive amount of an antido-te of formula I, ei-ther as such or in -the form of a sui-table composi-tion.
The invention of the copending; application also discloses and claims compositions containing a compound of formula I as an ac-tive ingredien-t along with inert vehicles and optionally other additives useful -to trea-t the seeds of useful plan-ts, the plan-ts themselves or -the soil in which -they grow.
The appLicationalso discloses and claims see~s o.E useful plants treated with an effective amount of a compound of formula The compounds of formul.a I may also be in the form of sa~ts, e.g. hyrochlorides, when in formu:La :t 1~1=11.
For the uses according to the invention of the copend-ing applica-tion, -the individual compounds oi~ formula I, also in admix-ture with one ano-ther, and the corresponding sal-ts are equally valid.
Some of the compounds of formula I are known, namely:
2-thiazolidine-carboxylic acid and the lower alkyl es-ters thereof, 4-thiazolidine-carboxylic acid and the lower alkyl esters thereof, N-acetyl-2-th:iazolidi.ne-carboxylic acid, the methyl este:r of N-d.ichloroacety:L-4-th:iazol:idine-carboxy:~.ic ac:id,and N-acety.L-4-th:Lazoli.dine-carboxyll.c ac:i.d.
Some of these known compounds, such as tl-le derivatives of 4--thiazolidine-carboxylic acid, are useful as bios-timulan-ts for agrarian uses. I'he others have been tested in the pharmaceu-tical field as hepatoprotectors or intermediates for antibio-tics.
As far as we know, these compounds were never supposed -to be associated with proper-ties of antidotes for herbicides.
~v~
The compounds oE Eormula I are easily preparable by acylation o.E 2- or 4-thiazolidine-carboxylic acid or oE the res-pective alkyl esters with the suitable haloacetyl chloride, in an inert solvent and in the presence o:E a halohydric acid-accepting base.
As an alternative, acylation can be accomplished by subs-ti-tuting the acyl halide by the corresponding anhydride.
The following compounds; N-dichloracetyl-2-thiazolidine-carboxylic acid HO-C--<
t NJ
f~-C~IC12 [metl-ting poin-t = 136-140 C; IR (cm ) : 1710 (~J COOH), 1660 l~) CO-N)], methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid ~S
\NI--~-CHC12 ~melting point = 80-81 C; IR (cm ): 1740 ( COOCH3), 1670 (`J CO-N)] are new and :Eorm the subject ma-tter oE the presen-t in-ven-tion.
It has been furthermore observed tha-t N-acetyl-2--thiazolidi.ne-carboxylie aeid and the esters thereof with Cl-C~
alcohols possess, besides antidotic properties, also biostimula-t-ing properties.
The action of these compounds, when employed as biosti-mulants, results in a more luxuriant aspeet of the plants and in an increase in -the harvest.
Thus, -the inven-tion of the copending application pro-vides for -the use of N-aee-tyl-2-thiazolidine-carboxylie aeid and 10 of its esters with Cl-C~ aleohols as biostimulan-ts for eul-tiva-tions of agrarian interest.
As menti.oned hereinbefore, the antidotes of formula I
ean be appii.ed to the useful eultivat:ions aeeordirlg to various rnoclalities.
Z3~:L
For example, they can be utilized for a preventive treatmen-t of seeds, so that the plants developing thereErom wlll be pro-tec-ted from the toxic actlon exer-ted by nonselec-tive herbicides.
As an alternative, -the compounds of formula I are employable for treating the plant itself or the soil in which it grows. In this case, the antidotes can be distributed alone or in combination with the nonselective herbicides.
The different types of applications require diEfer~
ent conditions which affect the practical aspects of the -treatment, such as antidote amoun-t, period of treatment and type of composition.
Other :Eactors in:Eluencing the practical aspects oE
the treatment are the type oE cultivation to be protected, the non~selective herbicide employed, the climatic and environ-mental conditions.
When the antidote is applied in a preventive seed treatment, it is employable as such or, preferably, as a proper composition.
2Q The compositions for the treatment of the seeds may be in the form of powders, wetable powders or emulsiEiable concentrates, and generally consist of the active compound in amounts ranging from 0.5 to 95% by weight and of the usual inert vehicles \
~23;~
I which, depending on the composition type, may be solid, ¦ such as -talc, silica, diatomite, ben-toni-te, calcium carbon-~ a-te and mixtures thereoE, or liquid, such as water, alkyl-¦ aroma-tic hydrocarbons, acetone, cyclohe~anone and mixtures thereoE.
The compositions may also contain suitable addi-tives, such as surfac-tants, wetting agents, dispersants and mixtures thereof.
As previously cited, -the antidote amount -to be distributed on -the seeds vaLies as a function of various factors, however, it is generally suEficient to use product amounts ranging Erom 0.1 to 100 g/Kg oE seeds.
The treatments directly eEEected on the plant or in the medium where the plant grows require, oE course, that the antidote be used in the form of a suitable composi-tion according to the usual practice for this kind of appli-cation.
In the applications in which the antidote is distri-buted on the vegetation or into the soil along with the non-selective herbicide in a single formulation, the type of formulation and the content vary both as a function o:E the above-mentioned factors, and as a func-tion of the herbicide type utilized and of the characteristics thereof.
The anticlote amoun-t to be used ranges from 0.1 to 10 Kg/ha and the ratio between an-tidote and herbicide in the composition may range from 1:5 to 5:1.
~ ~r~
The following examples are given to better illus-trate the present invention.
Example 1 ~ntidotic Activity in Maize Plants by Preventive Treatment of the Seeds General modalities: 60 maize seeds were treated with 60 or 120mg of the antidote to be tested, dissolved in 3ml of an aqueous solu-tion of dimethylsulphoxide (DMSO) at 3% by weight, or in 3ml of water optionally containing a wetting agent at 0.1%.
On a basis oE 60,000 seeds/ha, the dose employed was corresponding to 6~ or to ].20CJ oE antidote per hectare, or corresponding to 2. 8 or 5.6g of antidote per Kg. of seeds.
The treatment was accomplished by mixing the seeds for 10 minutes in said solution and then by allowing them to dry during 24 hours, stirring them at interva]s in the course of the first hours.
The treated seeds were then sowed a ground pre-viously treated with the weed-killer heing tested, a-t a predetermined dose. As a control, also mai~e seeds leEt in a water bath not containing an~ antidote, under the same condi-tions, were sowed.
After a 10-day growth under continuous light and at a temperature o~ 25C, the antidotic activity was evalu-ated by comparing the growth of the plants treated with the weed-killer and with the g ?
,;.,~.~s~ j . ~ .~. ~, ~2~23~a weed-killer plus the antido-te, wi-th the grow-th of the plants -trea-ted neither wi-th the weed-killer nor with the antidote.
In the an-tidotic act.ivi-ty -tests, the following compounds oE
~ormula I were tested A = N-acetyl-4-thiazolidine-carboxylic acld = 4-thiazolidine-carboxylic acid C = 2-thiazolidine-carboxylic acid D = N-acetyl-2-thiazolidine-carboxylic acid E = methyl ester of N-dichloroacetyl--4-thiazolidine-carboxylic ac.id F = N-dichloroacetyl-2-thiazolidine-carboxylic acid G = methyl ester of acid C
H = methyl ester of acid F
I = methyl ester oE N-chloroacetyl-~-thiazolidine-carboxylic acid.
The herbicides employed wexe Alachlor (chloroace-tanilide) and Eptam (thiolcarbamate).
The results recorded on Eollowing Tables 1 and 2 reEer to the toxic action of the herbicide in the presence of the antidote on the maize plants and are expressed accordin~
to a scale of values Erom 4 (complete stop o:E growth or death of the plant) to 0 (plant growth like that of plants not trea-ted with herbicide and antidote).
. . , ~2~23~
As a consequence, an evalua-tion equal to that of the herbicide alone is indicative of the absence of an antidotic effect, while lower values are indicative of an an-tidotic effect increasing towards the lower values.
Preliminary laboratory tests proved that -the anti-do-tes of formula I are not toxic for ma:ize and that the herbicide activity o~ Ala.chlor and Eptarn towards the common infesting plants of maize (Solanum nigrum, Amarantus spp., Echinochloa spp., Digitaria Spp., Setaria spp., Sorghurn_ _~lepense, Panichum dichotomiElorum, ~yperus rotundus, Cyperus esclulantus) is not a:Efected by -the presence of ....
the antidote in this kind of tests.
`; ~
J Table 1 ~ Antidotic ac-tivity by preventlve trea-tment oE maize seeds.
Some of these known compounds, such as tl-le derivatives of 4--thiazolidine-carboxylic acid, are useful as bios-timulan-ts for agrarian uses. I'he others have been tested in the pharmaceu-tical field as hepatoprotectors or intermediates for antibio-tics.
As far as we know, these compounds were never supposed -to be associated with proper-ties of antidotes for herbicides.
~v~
The compounds oE Eormula I are easily preparable by acylation o.E 2- or 4-thiazolidine-carboxylic acid or oE the res-pective alkyl esters with the suitable haloacetyl chloride, in an inert solvent and in the presence o:E a halohydric acid-accepting base.
As an alternative, acylation can be accomplished by subs-ti-tuting the acyl halide by the corresponding anhydride.
The following compounds; N-dichloracetyl-2-thiazolidine-carboxylic acid HO-C--<
t NJ
f~-C~IC12 [metl-ting poin-t = 136-140 C; IR (cm ) : 1710 (~J COOH), 1660 l~) CO-N)], methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid ~S
\NI--~-CHC12 ~melting point = 80-81 C; IR (cm ): 1740 ( COOCH3), 1670 (`J CO-N)] are new and :Eorm the subject ma-tter oE the presen-t in-ven-tion.
It has been furthermore observed tha-t N-acetyl-2--thiazolidi.ne-carboxylie aeid and the esters thereof with Cl-C~
alcohols possess, besides antidotic properties, also biostimula-t-ing properties.
The action of these compounds, when employed as biosti-mulants, results in a more luxuriant aspeet of the plants and in an increase in -the harvest.
Thus, -the inven-tion of the copending application pro-vides for -the use of N-aee-tyl-2-thiazolidine-carboxylie aeid and 10 of its esters with Cl-C~ aleohols as biostimulan-ts for eul-tiva-tions of agrarian interest.
As menti.oned hereinbefore, the antidotes of formula I
ean be appii.ed to the useful eultivat:ions aeeordirlg to various rnoclalities.
Z3~:L
For example, they can be utilized for a preventive treatmen-t of seeds, so that the plants developing thereErom wlll be pro-tec-ted from the toxic actlon exer-ted by nonselec-tive herbicides.
As an alternative, -the compounds of formula I are employable for treating the plant itself or the soil in which it grows. In this case, the antidotes can be distributed alone or in combination with the nonselective herbicides.
The different types of applications require diEfer~
ent conditions which affect the practical aspects of the -treatment, such as antidote amoun-t, period of treatment and type of composition.
Other :Eactors in:Eluencing the practical aspects oE
the treatment are the type oE cultivation to be protected, the non~selective herbicide employed, the climatic and environ-mental conditions.
When the antidote is applied in a preventive seed treatment, it is employable as such or, preferably, as a proper composition.
2Q The compositions for the treatment of the seeds may be in the form of powders, wetable powders or emulsiEiable concentrates, and generally consist of the active compound in amounts ranging from 0.5 to 95% by weight and of the usual inert vehicles \
~23;~
I which, depending on the composition type, may be solid, ¦ such as -talc, silica, diatomite, ben-toni-te, calcium carbon-~ a-te and mixtures thereoE, or liquid, such as water, alkyl-¦ aroma-tic hydrocarbons, acetone, cyclohe~anone and mixtures thereoE.
The compositions may also contain suitable addi-tives, such as surfac-tants, wetting agents, dispersants and mixtures thereof.
As previously cited, -the antidote amount -to be distributed on -the seeds vaLies as a function of various factors, however, it is generally suEficient to use product amounts ranging Erom 0.1 to 100 g/Kg oE seeds.
The treatments directly eEEected on the plant or in the medium where the plant grows require, oE course, that the antidote be used in the form of a suitable composi-tion according to the usual practice for this kind of appli-cation.
In the applications in which the antidote is distri-buted on the vegetation or into the soil along with the non-selective herbicide in a single formulation, the type of formulation and the content vary both as a function o:E the above-mentioned factors, and as a func-tion of the herbicide type utilized and of the characteristics thereof.
The anticlote amoun-t to be used ranges from 0.1 to 10 Kg/ha and the ratio between an-tidote and herbicide in the composition may range from 1:5 to 5:1.
~ ~r~
The following examples are given to better illus-trate the present invention.
Example 1 ~ntidotic Activity in Maize Plants by Preventive Treatment of the Seeds General modalities: 60 maize seeds were treated with 60 or 120mg of the antidote to be tested, dissolved in 3ml of an aqueous solu-tion of dimethylsulphoxide (DMSO) at 3% by weight, or in 3ml of water optionally containing a wetting agent at 0.1%.
On a basis oE 60,000 seeds/ha, the dose employed was corresponding to 6~ or to ].20CJ oE antidote per hectare, or corresponding to 2. 8 or 5.6g of antidote per Kg. of seeds.
The treatment was accomplished by mixing the seeds for 10 minutes in said solution and then by allowing them to dry during 24 hours, stirring them at interva]s in the course of the first hours.
The treated seeds were then sowed a ground pre-viously treated with the weed-killer heing tested, a-t a predetermined dose. As a control, also mai~e seeds leEt in a water bath not containing an~ antidote, under the same condi-tions, were sowed.
After a 10-day growth under continuous light and at a temperature o~ 25C, the antidotic activity was evalu-ated by comparing the growth of the plants treated with the weed-killer and with the g ?
,;.,~.~s~ j . ~ .~. ~, ~2~23~a weed-killer plus the antido-te, wi-th the grow-th of the plants -trea-ted neither wi-th the weed-killer nor with the antidote.
In the an-tidotic act.ivi-ty -tests, the following compounds oE
~ormula I were tested A = N-acetyl-4-thiazolidine-carboxylic acld = 4-thiazolidine-carboxylic acid C = 2-thiazolidine-carboxylic acid D = N-acetyl-2-thiazolidine-carboxylic acid E = methyl ester of N-dichloroacetyl--4-thiazolidine-carboxylic ac.id F = N-dichloroacetyl-2-thiazolidine-carboxylic acid G = methyl ester of acid C
H = methyl ester of acid F
I = methyl ester oE N-chloroacetyl-~-thiazolidine-carboxylic acid.
The herbicides employed wexe Alachlor (chloroace-tanilide) and Eptam (thiolcarbamate).
The results recorded on Eollowing Tables 1 and 2 reEer to the toxic action of the herbicide in the presence of the antidote on the maize plants and are expressed accordin~
to a scale of values Erom 4 (complete stop o:E growth or death of the plant) to 0 (plant growth like that of plants not trea-ted with herbicide and antidote).
. . , ~2~23~
As a consequence, an evalua-tion equal to that of the herbicide alone is indicative of the absence of an antidotic effect, while lower values are indicative of an an-tidotic effect increasing towards the lower values.
Preliminary laboratory tests proved that -the anti-do-tes of formula I are not toxic for ma:ize and that the herbicide activity o~ Ala.chlor and Eptarn towards the common infesting plants of maize (Solanum nigrum, Amarantus spp., Echinochloa spp., Digitaria Spp., Setaria spp., Sorghurn_ _~lepense, Panichum dichotomiElorum, ~yperus rotundus, Cyperus esclulantus) is not a:Efected by -the presence of ....
the antidote in this kind of tests.
`; ~
J Table 1 ~ Antidotic ac-tivity by preventlve trea-tment oE maize seeds.
3 Herbicide: Alachlor :, An-tidote g of anti- Antidote Toxic action on maize ex-dote/lO00 solution erted by the herbicide at g of seeds a dose of:
16 Kg/ha 8 Kg/ha ¦ A 2.8 H2O 2 2 B 2.8 H2O 2-3 2-3 C. 2.8 H2O .l D 2.8 H2O 2 E 2.8 H2O/DMSO 3% 2 F 2.8 H2O/DMSO 3% l 0 G 2O8 H2O/DMSO 3% 2 H 2.8 H2O/DMSO 3% 1--2 0 -il Table 2 An-tidotic activity by preventive trea-tment of maize seeds.
Herbicide: Eptam Antidote g of anti- Anticlote Toxic action on maize ex-dote/1000 g solution erted by the weed-killer of seeds (1) at a dose of:
16 Kg/ha 8 Kg/ha ¦ A 2.8 H2O 2 2 B 2.8 H2O 2-3 2-3 C. 2.8 H2O .l D 2.8 H2O 2 E 2.8 H2O/DMSO 3% 2 F 2.8 H2O/DMSO 3% l 0 G 2O8 H2O/DMSO 3% 2 H 2.8 H2O/DMSO 3% 1--2 0 -il Table 2 An-tidotic activity by preventive trea-tment of maize seeds.
Herbicide: Eptam Antidote g of anti- Anticlote Toxic action on maize ex-dote/1000 g solution erted by the weed-killer of seeds (1) at a dose of:
4 Kg/ha2 Kg/ha _ _ - 3 2 C 2.8H2O/DMSo 3% 2 C 5.6~-12O/D~SO 3% 1 0 C 2.8H2O/wettiny agen-t 0.1% 1 0 C 5.6H2O/wetting agent 0.1% 1 0 C 2.8H2O/wetting agent 0.5% 0 G 2.8~I2O/DMSO 3% 2 F 2.8H2O/DMSO 3% 0 0 H 2.8H2O/DMSO 3~ 0 0 I 2.8H2O~DMSO 3% 2-3 Notes to Table 2 (1) As a wetting agent there was indifferently utilized "Tween 20" (registered trademark of Atlas Co. for sorbitane monolaurate polyoxyethylated with 20 moles of ethylene oxide per mole of substrate) or "Emulson 20 OM" (registered trademark of ROL Co. for sorbitane oleate polyoxyethylated with 20 moles of ethylene oxide per mole of substrate).
~:,
~:,
Claims (11)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of reducing the damage caused to useful cultivations by herbicides belonging to the class of chloroace-tanilides or of thiolcarbamates which comprises treating seeds, plants or the soil in which they grow with an effective amount of a compound acting as an antidote selected from N-dichloroacetyl-2-thlazolidine carboxylic acid and the methyl ester of N-dichloroacetyl-2-thia-zolidine-carboxylic acid.
2. The method according to claim 1, in which the anti-dote is applied in the form of a composition in association with a suitable carrier.
3. The method according to claim 1, in wich the anti-dote is applied in the preventive treatment of the seeds of use-ful plants.
4. The method according to claim 1, in which the non-selective herbicide belongs to the class of the chloroacetani-lides.
5. The method according to claim 4, in which the her-bicide belonging to the class of the chloroactanilides is N-methoxymethyl-2,6-diethyl-chloroacetanilide.
6. The method according to claim 1, in which the non-selective herbicide belongs to the class of the thiolcarbamtes.
7. The method according to claim 6, in which the her-bicide belonging to the class of the thiolcarbamates is N,N-dipropyl-S-ethyl-thiolcarbamte.
8. A method according to claim 1, 2 or 3, in which the herbicide is selected from N-methoxymethyl-2,6-diethyl-chloroacetanilide, N-butoxymethyl-2,6-diethyl-chloroacetanilide N-methoxyethyl-2-methyl-6-allyl-chloroacetanilide, N,N-diisopropyl S-(2,3-dichloroallyl)-thiolcarbamate, N,N-diethyl-S-(4-chloro-benzyl)-thiolcarbamate and N,N-dipropyl-S-ethyl-thiolcarbamate.
9. Seeds of useful plants treated with an antidote of formula I given in claim 1.
10. A compound selected from N-dichloroacetyl-2-thia-zolidine-carboxylic acid and the methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid.
11. N-dichloroace-tyl-2-thiazolidine-carboxylic acid.
l2. The methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid.
l2. The methyl ester of N-dichloroacetyl-2-thiazolidine-carboxylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000477061A CA1202311A (en) | 1982-03-19 | 1985-03-20 | Method of protecting cultivations of agrarian interest from the action of non selective herbicides |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20272/82A IT1150707B (en) | 1982-03-19 | 1982-03-19 | METHOD FOR THE DEFENSE OF CROPS OF AGRICULTURAL INTEREST BY THE ACTION OF NON-SELECTIVE HERBICIDES |
| IT20272A/82 | 1982-03-19 | ||
| CA000423894A CA1207161A (en) | 1982-03-19 | 1983-03-18 | Method of protecting cultivations of agrarian interest from the action of non selective herbicides |
| CA000477061A CA1202311A (en) | 1982-03-19 | 1985-03-20 | Method of protecting cultivations of agrarian interest from the action of non selective herbicides |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000423894A Division CA1207161A (en) | 1982-03-19 | 1983-03-18 | Method of protecting cultivations of agrarian interest from the action of non selective herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1202311A true CA1202311A (en) | 1986-03-25 |
Family
ID=25669971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000477061A Expired CA1202311A (en) | 1982-03-19 | 1985-03-20 | Method of protecting cultivations of agrarian interest from the action of non selective herbicides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1202311A (en) |
-
1985
- 1985-03-20 CA CA000477061A patent/CA1202311A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |