CA1168886A - Method and agent for selective control of weeds in corn - Google Patents
Method and agent for selective control of weeds in cornInfo
- Publication number
- CA1168886A CA1168886A CA000190455A CA190455A CA1168886A CA 1168886 A CA1168886 A CA 1168886A CA 000190455 A CA000190455 A CA 000190455A CA 190455 A CA190455 A CA 190455A CA 1168886 A CA1168886 A CA 1168886A
- Authority
- CA
- Canada
- Prior art keywords
- antidote
- formula
- maize
- dichloracetamide
- allyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
Abstract
ABSTRACT OF THE DISCLOSURE
The present invention is concerned with a method for selective control of weeds in corn, (maize) wherein a highly active and non selective herbicide, N-(2'-methoxyethyl)-2,6-dimethyl-chloracetanilide is applied before or after emergence/together with a safening agent (antidote) selected from a small group of N,N-disubstituted dichloro-acetamides.
The invention is also concerned with compositions including such herbicides and safeners.
The present invention is concerned with a method for selective control of weeds in corn, (maize) wherein a highly active and non selective herbicide, N-(2'-methoxyethyl)-2,6-dimethyl-chloracetanilide is applied before or after emergence/together with a safening agent (antidote) selected from a small group of N,N-disubstituted dichloro-acetamides.
The invention is also concerned with compositions including such herbicides and safeners.
Description
It is known that many herbicides in important crops of cultivated plants have no, or too little, selective action, i.e. in addition to the weeds to be destroyed they also injure the cultivated plants to a greater or lesser degree. This applied to most classes of herbicide, e.g. triazines, urea derivatives, carbamates, thiolcarbamates, haloacetanilides etc.
This property has particularly disadvantageous conse-quences in large scale crops, such as cereals and maize, and despite successful efforts to find herbicides of good selectivity, this problem has still not been completely satisfactorily solved.
On the other hand, substances have been proposed for pretreating seeds, e.g. for providing cereal and maize seeds with protective layers before sowing in order to make them resistant to specific herbicides. Both the protective agent and the herbi-cide are very largely species-specific with respect to the culti-vated plant. Thus in German Offenlegungsschrift 1.952.910 issued June 25, 1970 to Gulf and in French patent 2.021.611 issued July 24, 1970 to Gulf, the use of 1,8-naphthalic acid derivatives, oxamic acid derivatives ~derivatives of the oxylic monoamide HOOC-CONH2) and malonic diamide has been proposed for treating cereal and maize seeds in order to protect these against attack by herbicidal N,N-dialkylated thiocarbamic acid-S-alkyl esters.
Earlier, proposals had already been made for treating cereal seeds with the most diverse substances, such as hydroxyaminoacetanilide, dichloroxanthenones, hydantoins, isopropyldithiocarbamate salts, N-methyl-dichlorobenzene-sulphonamide etc.~ in order to protect the seeds against *he action of herbicidal carbamates, such as IPC, CIPC ~German patent 1.576.076 issued 1968 to Gulf, United States patent 3.131.509 issued May 5, 1968 to Gulf).
Of more recent date are publications relating to the ~' . .
; ~; - 2-, . . .
.
~ 1 ~i8~38~
treatment of the seeds and shoots of corn and sorghum with N,N-disubstituked oxamic acid esters, diallyl proprionamide, diallyl acetamide, naphthalates etc. in order to protect these against attack by N-methoxymethyl-~2',6'-diethylchloroacetanilide) cf.
British patent 1.277.557 issued June 14, 1972 to Gulf.
This particular seed treatment before sowing entails substantial economic disadvantages, in particular the expenditure in terms of labour and money involved in the special steps carried out in special mixing devices for the large amounts of seeds which are sown in large-scale crops.
Attempts have therefore already been made to find what are known as safening agents or antidotes which can be applied not to the seeds, but either together with, or before or after, the herbicidal applica*ion to the crop area to be sown, or which has already been sown (preemergent treatment), or after the seeds have germinated ~post-emergent treatment), and which have the same pro-tective effect, i.e. they cause the non-selective herbicide to act selectively in that the weeds are damaged as much as possible with-out any more injury to the cultivated plants. Belgian patent 771.928 issued February 29, 1972 to Stauffer and German Offenle-gungsschrift ~Stauff0r) describe such an agent for protecking cereals against the herbicidal action of thiolcarbamates and ~riazines.
Besides these herbicides, this agent contains antidote halogenated alkanesulphonates of the type X- ~CH2) -0-S02-R
herein X represents a halogen atom, R represents alkyl, haloalkyl, halogen, acetoxy(halo)-alkyl, aryl, and n is a whole number from 1 to 5.
~ere too a pronounced species-specificity of the herbicides and the antidote on cereals is evident.
Finally, there has recently appear0d a publication ~German Offenlegungsschrift 2.218.097 issued October 14, 1972 to Stauffer) in whic}l, besides a straight forward pretreatment of the seeds with halogenated alkoylamides, there are also described herbicidal agents which contain such haloalkoylamides as antidotes.
The majority of the antidotes described and tested therein are used specifically with respect to the active com-ponents in the application o~ herbicidal thiolcarbamates and mixtures thereof with other herbicidal active substances. The emphasis is clearly on antagonising undesirable injury to the crop plants by thiolcarbamates. It is true that this publica-tion does also mention among the herbicides to be protected ckloroacetanilides as mixture components and individual active substances. However, the individual tests with such active substances refer only to two her~icides of this type, namely ~ N-methoxymethyl-2,6-diethyl-chloro-acetanilide ~"~ASSO") without ~, antidote and with an uneconomic surplus of an antidote in sorghum vulgare, and N-isopropyl-chloroacetanilide ~"RA~ROD") without antidote and with a surplus of antidote in corn. Despite the surplus of antidote, the result in both cases was far from con-vincing, the decrease in injury of the crop plant with the anti-dote moderate, and the ultimate injury determined still consider-able (20%). It is known that, in contradistrinction to other and recent, more active chloroacetanilides, no antidote at all is required when applying these two herbicides to maize.
It is probably for this reason that, despite a vast number o tests, this publication contains no further examples witk ckloroacetanilides as herbicides. Evidently, the applicant of German Offenlegungsschrift 2.212.268 issued ~ dcl O ~h ~ rK, -- ~ 1 3 ~86 September 28, 1972 to Sumetomo has not realised the exceptional-ly important fact that other more active chloroacetanilides of different constitut:ion can be conspicu-.
e ously improved in their selective ~ct$vlty against weeds incereals and maize by small amounts oE some of the antidotes proposed by her, and for this reago~ has proposed these antidotes with proved success onl~ together with thiolcarha-mates as herbicides.
Whereas certain herbicides oE the triazine and phenylurea series are already knwon ~or the selective control of weeds in cereals and maize and ~e con~lercially available, it has not been possible to avail ~f more recent haloacetani-lides to the desired extent on ac~ount o~ their generally unsatisfactory selectivity in cereQl and ~aize plantations, since they cause severe injury to these crop plants, which means diminishedyield, and still no effective antidote against such haloacet~nilides has become known.
Specific disclosure of _he invention The surprisin~ discovery has now been made that~ contrary to the presumptions to be inferred Erom the literature, it is possible to impart firstrat~ protection to n~ize plan~s from injury by ~he above mèntiohed herbicidal chloracetanilide by treating the ~oll with a N,N-di-substituted dichloracetamide.
This invention is concerned ~itb a ~ethod Eor the selective control of weeds in ~or~ (maize) which comprises treating the crop areas $o~ th~ cultivation of maize with the chloracetanilidè hè~bl~ide.
N-(2'-methoxyethyl)-2,6-di~ethyl-~hloracetanilide of formula :
CH
3 / C2~40C~l3 \ COC~IzC
~ blch is known from Canadi.an Patent (a-pplication Ser. No, 162 4~0) or British Patent No. 1 422 473 together with a saEening agent (antidote), selected from the group o~ N,N-dig~bstlt~ted dichloracetamides corresponding to the formula II
This property has particularly disadvantageous conse-quences in large scale crops, such as cereals and maize, and despite successful efforts to find herbicides of good selectivity, this problem has still not been completely satisfactorily solved.
On the other hand, substances have been proposed for pretreating seeds, e.g. for providing cereal and maize seeds with protective layers before sowing in order to make them resistant to specific herbicides. Both the protective agent and the herbi-cide are very largely species-specific with respect to the culti-vated plant. Thus in German Offenlegungsschrift 1.952.910 issued June 25, 1970 to Gulf and in French patent 2.021.611 issued July 24, 1970 to Gulf, the use of 1,8-naphthalic acid derivatives, oxamic acid derivatives ~derivatives of the oxylic monoamide HOOC-CONH2) and malonic diamide has been proposed for treating cereal and maize seeds in order to protect these against attack by herbicidal N,N-dialkylated thiocarbamic acid-S-alkyl esters.
Earlier, proposals had already been made for treating cereal seeds with the most diverse substances, such as hydroxyaminoacetanilide, dichloroxanthenones, hydantoins, isopropyldithiocarbamate salts, N-methyl-dichlorobenzene-sulphonamide etc.~ in order to protect the seeds against *he action of herbicidal carbamates, such as IPC, CIPC ~German patent 1.576.076 issued 1968 to Gulf, United States patent 3.131.509 issued May 5, 1968 to Gulf).
Of more recent date are publications relating to the ~' . .
; ~; - 2-, . . .
.
~ 1 ~i8~38~
treatment of the seeds and shoots of corn and sorghum with N,N-disubstituked oxamic acid esters, diallyl proprionamide, diallyl acetamide, naphthalates etc. in order to protect these against attack by N-methoxymethyl-~2',6'-diethylchloroacetanilide) cf.
British patent 1.277.557 issued June 14, 1972 to Gulf.
This particular seed treatment before sowing entails substantial economic disadvantages, in particular the expenditure in terms of labour and money involved in the special steps carried out in special mixing devices for the large amounts of seeds which are sown in large-scale crops.
Attempts have therefore already been made to find what are known as safening agents or antidotes which can be applied not to the seeds, but either together with, or before or after, the herbicidal applica*ion to the crop area to be sown, or which has already been sown (preemergent treatment), or after the seeds have germinated ~post-emergent treatment), and which have the same pro-tective effect, i.e. they cause the non-selective herbicide to act selectively in that the weeds are damaged as much as possible with-out any more injury to the cultivated plants. Belgian patent 771.928 issued February 29, 1972 to Stauffer and German Offenle-gungsschrift ~Stauff0r) describe such an agent for protecking cereals against the herbicidal action of thiolcarbamates and ~riazines.
Besides these herbicides, this agent contains antidote halogenated alkanesulphonates of the type X- ~CH2) -0-S02-R
herein X represents a halogen atom, R represents alkyl, haloalkyl, halogen, acetoxy(halo)-alkyl, aryl, and n is a whole number from 1 to 5.
~ere too a pronounced species-specificity of the herbicides and the antidote on cereals is evident.
Finally, there has recently appear0d a publication ~German Offenlegungsschrift 2.218.097 issued October 14, 1972 to Stauffer) in whic}l, besides a straight forward pretreatment of the seeds with halogenated alkoylamides, there are also described herbicidal agents which contain such haloalkoylamides as antidotes.
The majority of the antidotes described and tested therein are used specifically with respect to the active com-ponents in the application o~ herbicidal thiolcarbamates and mixtures thereof with other herbicidal active substances. The emphasis is clearly on antagonising undesirable injury to the crop plants by thiolcarbamates. It is true that this publica-tion does also mention among the herbicides to be protected ckloroacetanilides as mixture components and individual active substances. However, the individual tests with such active substances refer only to two her~icides of this type, namely ~ N-methoxymethyl-2,6-diethyl-chloro-acetanilide ~"~ASSO") without ~, antidote and with an uneconomic surplus of an antidote in sorghum vulgare, and N-isopropyl-chloroacetanilide ~"RA~ROD") without antidote and with a surplus of antidote in corn. Despite the surplus of antidote, the result in both cases was far from con-vincing, the decrease in injury of the crop plant with the anti-dote moderate, and the ultimate injury determined still consider-able (20%). It is known that, in contradistrinction to other and recent, more active chloroacetanilides, no antidote at all is required when applying these two herbicides to maize.
It is probably for this reason that, despite a vast number o tests, this publication contains no further examples witk ckloroacetanilides as herbicides. Evidently, the applicant of German Offenlegungsschrift 2.212.268 issued ~ dcl O ~h ~ rK, -- ~ 1 3 ~86 September 28, 1972 to Sumetomo has not realised the exceptional-ly important fact that other more active chloroacetanilides of different constitut:ion can be conspicu-.
e ously improved in their selective ~ct$vlty against weeds incereals and maize by small amounts oE some of the antidotes proposed by her, and for this reago~ has proposed these antidotes with proved success onl~ together with thiolcarha-mates as herbicides.
Whereas certain herbicides oE the triazine and phenylurea series are already knwon ~or the selective control of weeds in cereals and maize and ~e con~lercially available, it has not been possible to avail ~f more recent haloacetani-lides to the desired extent on ac~ount o~ their generally unsatisfactory selectivity in cereQl and ~aize plantations, since they cause severe injury to these crop plants, which means diminishedyield, and still no effective antidote against such haloacet~nilides has become known.
Specific disclosure of _he invention The surprisin~ discovery has now been made that~ contrary to the presumptions to be inferred Erom the literature, it is possible to impart firstrat~ protection to n~ize plan~s from injury by ~he above mèntiohed herbicidal chloracetanilide by treating the ~oll with a N,N-di-substituted dichloracetamide.
This invention is concerned ~itb a ~ethod Eor the selective control of weeds in ~or~ (maize) which comprises treating the crop areas $o~ th~ cultivation of maize with the chloracetanilidè hè~bl~ide.
N-(2'-methoxyethyl)-2,6-di~ethyl-~hloracetanilide of formula :
CH
3 / C2~40C~l3 \ COC~IzC
~ blch is known from Canadi.an Patent (a-pplication Ser. No, 162 4~0) or British Patent No. 1 422 473 together with a saEening agent (antidote), selected from the group o~ N,N-dig~bstlt~ted dichloracetamides corresponding to the formula II
2 -~ N - CO - CHC12 (II) .1 ' wherein Rl and R2 are individually allyl or lower alkyl radicals or together with the nitrogen atom form the 1,3-oxazolidine ring, which optionall.~ may be substituted by methyl radicals, said antidote being presen~ in a concentration of from about 0,01 to 1 part by welght per part by weight of said chLoracetanilide.
~ uch antidotes oE forlnul.a II a~ dlscl.osed in part in the German OfEenlegungsschrift No, 2 21B ~97.(Stauffer Feb. 29, 1972) It is conceivable that an a~tld~te ~hich is used in higher rates of application in ~e~e~i~ itself exerts a herbicidal action, but insmall amounts a~tagonises the herbicidal action of the chloroacetanlildes on maize.
' ~q ;~
Pre~erred antidotes of the ~rm~l~ II are ~H2~CH-CI-I
N-C0-C~ICl N,~-~iallyl-dichloroacetamide, ~H2aCH-CH2 nD ~ 1~5036 ~1l =C~I-C~
2 2~ N-eth~l-N-~lLyl-d3cllloro~ce~atllide () ~CI i(: 1., ~2H5 n2d ~ 1,4~54 ~H2=CH-c~l2.~ N-iæ~pr~pyl-N-a].lyl-dichlora oet-/ N-C0-CHC12 amide t 3)2 nD ~ i,4~1 2 C~l2 t~ N-CO-CHC12 N-d~ch~ o~cetyl-2,2-dimethyl.-9 3~bx~z~lidine m.p~ 121 C~
~ uch antidotes oE forlnul.a II a~ dlscl.osed in part in the German OfEenlegungsschrift No, 2 21B ~97.(Stauffer Feb. 29, 1972) It is conceivable that an a~tld~te ~hich is used in higher rates of application in ~e~e~i~ itself exerts a herbicidal action, but insmall amounts a~tagonises the herbicidal action of the chloroacetanlildes on maize.
' ~q ;~
Pre~erred antidotes of the ~rm~l~ II are ~H2~CH-CI-I
N-C0-C~ICl N,~-~iallyl-dichloroacetamide, ~H2aCH-CH2 nD ~ 1~5036 ~1l =C~I-C~
2 2~ N-eth~l-N-~lLyl-d3cllloro~ce~atllide () ~CI i(: 1., ~2H5 n2d ~ 1,4~54 ~H2=CH-c~l2.~ N-iæ~pr~pyl-N-a].lyl-dichlora oet-/ N-C0-CHC12 amide t 3)2 nD ~ i,4~1 2 C~l2 t~ N-CO-CHC12 N-d~ch~ o~cetyl-2,2-dimethyl.-9 3~bx~z~lidine m.p~ 121 C~
3 3 The invention therefore provlde~ a ~ethod ~or the selective control of weeds in maize cultu~es, which consists in treating the seeds or the crop ~e~ lhtended for ~he cultivation of maize in which the ~eed~ ~e to be SOWIl, or which have been sown, or in which thè s~ds have already germi~ ted, simultaneously or succéssl~el~, in optional !
~ ~ ~8~8~
sequer)ce and in an appropriate interval ~f time, on the one hand witll a lerbicide, tne chloroacetanilide of the formula I, and on the other with ~n antldote of the N,N-disubstituted dichloracetamide ~E the above formula II
which protects the germinated crop pl~nt~ and/or the seeds thereof.
The invention is also conce~ned with an agent for selective control of weeds in maize, which contains as herbicidally active component the chloro~cetanilide of the formula I as well as an atidote o~ the formula II.
These agents can be applied ~n any suitable form.
Thus they can be manuactured in known manner by intimately mixing and grinding the herbicidaly active substances and the antidote with suitable carriers and/or additives optio-nally accompanied by the addition of dispersants or sol-vents.
The conventional process ~orms a~e either solid, such as dusts, tracking agents, g~anùles, or liquid solu-tions, or they take the Eorm of actlve substance concentrates which can be dispersed in water, g~h ~9 wettable powder, emulsions, or pastes.
The agent according to the lnv~ntl~n i9 incorporated into the soil either beEore or afte~ th~ ~aize has been sown.
But naturally it is also possible t~ ~pply ~irst the herbi-'~
: ' .
cide and then the antidote to the ~oil, Finally, it wouldalso be possible to pre~reat the ~eeds themselves first with the antidote and then to so~ them in the soil, which has either been treated with the herblcide or in which the herbicide will later be incorporated. ~ is essential that the addition o~ the antidote doe~ not lmpair the herbicidal action oE the chloracetanilide ol1 th~ weeds.
The amount of antidote used varies between about 0.01 and abou~ 1 pflrt by weight pe~ p~t by welght oE
the haloacet~nilide. According ta cir~stances, i.e.
depending on the chloroacetanilide and àntidote used and the corp plant, the most suitable ~atio for attaining the most ideal actlvity is ascertainèd.
Experiments have proved, for example, that by treating sown maize fields with 2 kg/ha of a chloracetanilide alone there occured total injury after 3 1/2 weeks, but treatment with a mixture of the same amount of this chloro-acetanilide and 0.5 kg/ha of an ~ntidote caused no injury at all to the maize, while weeds s~ch as Sorghum hybridum, Echinochloa and Setaria were jus~ ~s ~ompletely destroyed as without the antidote.
'`
.~
~ 1 6~6 dependin~ on the chloroacetanilide and antidote used and the crop plant, the most suitable ratio for attaining the most ideal activity is ascertained.
Experiments have proved, for example, that by treating sown maize fields with 2 kg/ha of a chloroacetanilide alone there occurred total injury after 3 1/2 weeks; but treatment with a mixture of the same amount of this chloroacetanilide and 0.5 kg/ha o:E an antidote caused no injury at all to the maize~ while weeds such as Sorghum hybridum, Echinoclea and Setaria were just as completely destroyed as without the antidote.
Preferred antidotes of the formula II are CH2=CH- CH
\ N~N-diallyl-dichloroacetamide, / n20 = 1,5036 CH2=CH-CH2 D
CH2=CH-CH2 \ N-ethyl-N-allyl-dichloracetamide C2H5 nD = 1,4954 CH2=CH-CH2 \ N-isopropyl-N-allyl-dichloracetamide 3)2cH nD = 1,4921 -` / \ N-dichloroacetyl-2~2-dimethyl-1,3-0 / N-C0-CHC12 oxazolidine m.p. = 119-121 ' / \
The invention ~herefore provides a method for the selective control :
1 3 B~3B
of weeds in maize cultures, which consists in treating the seeds or the crop areas intended for the cultivation of maize in which the seeds are to ~e sown, or which have been sown, or in which the seeds have already germinated, simultaneously or successively, in optional saquence and in an appropriate interval of time, on the one hand with a herbicide, the chloroacetanilide of the formula I, and on the other with an antidote of the N,N-disubstituted dichloracetami.de of the above formula II which protects the germinated crop plants and/or the seeds thereof.
The invention is also concerned with an agent for selective control of weeds in maize, which contains as herbicidally active component the chloroacetanilide of the formula I as well as an atidote of the formula II.
~f The followil-~" ~ests were carried out to determine the selecti.ve herbicidal actinn of chloroacetanilides of the for~-nula I alone and togetheL with anti~otes of the , formula II:
Pre-emer~_nt ap~lication N-(2'-me~iloxyethyl)-2,6-dime~hy]-chloroace~an,i].ide (A) o the formula c~3 ~, ~/ C~l ~CH ~O-CH~
\~ N 2 2 J m.p. ~ 42~45 \===,~\ CO - CH 2C l was used as herbicidal active substance.
This compound was manufactured by reacting 2,6-dimethyl-aniline with methoxyacetaldehyde dissolved in benzene in the presence of trimethylamine by boiling to give 1-(2'-methoxy~ethylidene-amino)-2,6-dimethylbenzene (b.p. 58-61C/O.l Torr), converting this product by hydrogenation in ethanol with palladium-charcoal to N-(2'-methoxyethyl)-2,6-xylidine (b.p. 64C-65~C/0.2 Torr), and reacting this latter as a suspension together with potassium bicarbonate in benzene with chloroacetyl chloride.
N,N-diyllyl-dichloroacetamide (B) and N3-dichloroacetyl-2,2-dimethyl-1~3-oxyzolidine (C) were used as antido~,e, bo~h substances described in German OE~enlegungsschrift2.21$~0~7 g (Lxamples 1 and 42), as well as N-ethy'l.-N-al.lyl-dichloro-acetamide (D) and N-isopropyl--N-al].yl~dlchloroacetamide (E). Aqueous stock broths(suspenslorls) were prepared from wettable powders based on substances A, B, C, D, and E, and these suspenslons were applled 'both ~ingly and as mixtures, in the i.ndicated concentra~lons and mixture ratios, immediately after the test plants had been sown in seed dishes in a greenhouse, to the surface of t'he soil in the dishes, The seed dishes were then kept for 24 dags at 22 to 23C and 50% to 70% relative humidity while appropriately watering the dishes and the emergent plants.
The results were evaluated ater 13 and 24 days accordi.ng to a scale of rating from 1-9:
9 = plants not injured (as untreated control) 1 = plants completely withered 2 to 8 = intermediate stages of injury As test plants there were used:
crop plant: maize ("Orlea") [Zea]
weeds: Sorghum hybridum Echinochloa crus galli Setaria it.alica Digitaria sanguinalis Bromus tectorum The results are tabulated 'below, The amounts in kg/ha are in the ollowing relation to other units of measurement:
1 k~/ha = 0.1 ~/m2 _ 2 mg ~er l;tle of soil, the depth of the seed dishes i5 5 cm, so ~hat 1 m~ - 50 litres of soil.
Table I
, Herbicide A Antidote s Antidote B
amount in after 13 days after 24 days Plant kg/ha amo~mt in kg/ha amount in kg/ha 3 2 1 0,75 0,5 072! ,~ 2 1 ;0,75 0,5 0,25 . _ _ _ _ __ _ _ _ _ ~aize 0,25 9 9 9 9 0,5 ~ 9 8 9 0,75 7 9 6 9 1,0 6 9 9 5 9 9 2,0 ~ 7 8 ~ ~ 8 _ _~ _ _ __ _ _ _ ~ 9 8 9 9 9 9 9 9 Sorghum 0,25 2 2 1 2 0,5 1 2 1 1 0,75 1 1 1 1 1,0 1 1 1 1 1 2,0 1 1 1 ~ 1 1 _ _ _. _ _ _ _ _ _ crus galli 0,25 2 1 1 1 0,5 1 1 1 0,75 1 1 1 1 1,0 1 1 1 1 1 2,0 1 1 1 1 1 1 1 _ _ _ . _ _ _ _ _ __ Stealarica 0 55 1 5 1 1 1 1 7 9 1 1 2,0 1 1 1 1 1 1 1 _ _ _ _ _ _ Digitaria 0,25 1 1 1 sanguinalis 0,5 1 1 1 1 0,75 1 1 1 1 1,0 1 1 11 1 1 2,0 1 1 1 11 1 1 1 ..
- `
~ 1 6~
Table II
_ __ _ __ Herbicide A Antidote C Antidote C
amount iD after 13 days after 24 days Plant kg/ha amount kg/ha amount ln ~g~ha 0 2 l 0,75 ~0,5 0,2' 0 ~ l 0,75 0,5 0,75 _ __ ~ _ _ . _ _ _ Maize 0,25 9 9 9 9 (Orl~) 0,5 8 9 8 9 0,75 7 8 6 9 l,0 6 8 8 5 9 9 2,0 ~ 8 7 1~3 ~ 7 __ _ ~ _ l _ _ hybgrhiUdmum 0 25 2 9 9 2 2 1 9 9 2 2 ~,75 l 2 1 2 1,0 1 2 2 l 1 l 2,0 1 2 1 l l _ _ _ _ I i _ _ _ __ crus galli 0 25 2 l 1 1 l 0,75 1 1 1 l ~ . 1,0 1 1 1 1 1 1 2 0 1 1 l l l l l 1 _ ~ _ ~ _ I _ _ _ _ italica o,255 1 1 l 1 1 l 0,75 1 1 l l 1,0 1 1 1 1 1 1 _ 2,0 1 1 1 1 l l 1 .
Digitaria o 255 1 1 1 1 1 0,75 l l l l 1,0 1 1 1 1 1 1 2,0 1 ~ ~ l l 1 ~ l ---' ~- ~. .
I
$ 8 ~
Table II~
Pl.ant ~lerbicide A ¦ An~ldote D Antidote E
.~mount in 1 after 24 days after 24 c1ays kg/ha amoun~ in kg/ha amount in kg/ha O 21 l1 0,5 O 2 ~. 10.5 . ~ __. _~ I . ~.. ~ ~ ___ _ ~
O 9 9 g 9 9 9 ~ 9 l~aize 0,5 8 9 5 9 ~ 9 9 9 ~Orla) l,O 3 9 9 9 3 9 9 9 2,0 2 9 9 2 9 ~
~ ~ _ ~ __ ____ ___ _ __ .____ ___ O 9 9 9 ~ 9 9 9 9 Sorghum 0,5 2 2 2 2 2 2 2 l hybridum 1 0 2 21 2 2 21 21 21 2 . . __ _ _ ___~ _ ~___.
Echinochloa 0,5 l 1. l l l l l crus galli l,O l l l l l l l 2,0 l l l ~. l l _~ . _ __ _ ~
Setaria 0,5 2 l l l 2 l l italica l,O l l l 1 l l 1.
2,0 l l l l l l ~
_ _ _ _. _.__ . _ __ . __ __ : . O 9 9 9 9 9 9 9 9 Digitaria 0,5 l l l l l l l . 1,0 1 1 1 1 ' 1 1 1 sanguinalis 2,0 l l l l l 1.
_~ _ __ . _ ___ _ __ ~.
0,5 2 2 2 2 2 2 2 1 2 Bromus tectorum l,O l 2 l . l l l 2 1 l .~ . 2,0 l l l ~ 1 l l ___._~_ _ _ _ _ ___~
~ .
-,:
; . , , , , . .. ., . ., ....... .~ . ~.. . . ........ . . .. . . .. . . ... . ~
~ .
.
~ ~ 168~6 The results show clearly that the crop plant maize, which is virtually completely destroyed after 13 days using a rate o application of 2 kg/ha of herbicide A alone, suffers no more injury at all even after 24 days using the same amount of herbicide together with only 1/4 the amount ~0.5 kg/ha) of the antidote B, C, D or E, whereas all weeds are just as severely injured as without the antidote. It can even be seen that better results are often obtained with the application of smaller amounts of antidote than with larger ones. No surplus of antidote is therefore necessary and the ratio of antidote to herbicide can be 1:4.
It is advisable in practice, especially in regions with low rainfall, not only to apply the agent according to the invention to the surface of the soil, but to work it into the soil before the crop plants are sown~ thus preventillg only the perhaps more soluble herbicide from pene-trating into the soil when rainfall is slight and the antidote which remains on the surface from not being sufficiently active.
In the above tests, a surface treatment of the soil alone was sufficient to prove clearly an optimum effectiveness of the antidote lCI
~.~
~ ~ ~8~8~
sequer)ce and in an appropriate interval ~f time, on the one hand witll a lerbicide, tne chloroacetanilide of the formula I, and on the other with ~n antldote of the N,N-disubstituted dichloracetamide ~E the above formula II
which protects the germinated crop pl~nt~ and/or the seeds thereof.
The invention is also conce~ned with an agent for selective control of weeds in maize, which contains as herbicidally active component the chloro~cetanilide of the formula I as well as an atidote o~ the formula II.
These agents can be applied ~n any suitable form.
Thus they can be manuactured in known manner by intimately mixing and grinding the herbicidaly active substances and the antidote with suitable carriers and/or additives optio-nally accompanied by the addition of dispersants or sol-vents.
The conventional process ~orms a~e either solid, such as dusts, tracking agents, g~anùles, or liquid solu-tions, or they take the Eorm of actlve substance concentrates which can be dispersed in water, g~h ~9 wettable powder, emulsions, or pastes.
The agent according to the lnv~ntl~n i9 incorporated into the soil either beEore or afte~ th~ ~aize has been sown.
But naturally it is also possible t~ ~pply ~irst the herbi-'~
: ' .
cide and then the antidote to the ~oil, Finally, it wouldalso be possible to pre~reat the ~eeds themselves first with the antidote and then to so~ them in the soil, which has either been treated with the herblcide or in which the herbicide will later be incorporated. ~ is essential that the addition o~ the antidote doe~ not lmpair the herbicidal action oE the chloracetanilide ol1 th~ weeds.
The amount of antidote used varies between about 0.01 and abou~ 1 pflrt by weight pe~ p~t by welght oE
the haloacet~nilide. According ta cir~stances, i.e.
depending on the chloroacetanilide and àntidote used and the corp plant, the most suitable ~atio for attaining the most ideal actlvity is ascertainèd.
Experiments have proved, for example, that by treating sown maize fields with 2 kg/ha of a chloracetanilide alone there occured total injury after 3 1/2 weeks, but treatment with a mixture of the same amount of this chloro-acetanilide and 0.5 kg/ha of an ~ntidote caused no injury at all to the maize, while weeds s~ch as Sorghum hybridum, Echinochloa and Setaria were jus~ ~s ~ompletely destroyed as without the antidote.
'`
.~
~ 1 6~6 dependin~ on the chloroacetanilide and antidote used and the crop plant, the most suitable ratio for attaining the most ideal activity is ascertained.
Experiments have proved, for example, that by treating sown maize fields with 2 kg/ha of a chloroacetanilide alone there occurred total injury after 3 1/2 weeks; but treatment with a mixture of the same amount of this chloroacetanilide and 0.5 kg/ha o:E an antidote caused no injury at all to the maize~ while weeds such as Sorghum hybridum, Echinoclea and Setaria were just as completely destroyed as without the antidote.
Preferred antidotes of the formula II are CH2=CH- CH
\ N~N-diallyl-dichloroacetamide, / n20 = 1,5036 CH2=CH-CH2 D
CH2=CH-CH2 \ N-ethyl-N-allyl-dichloracetamide C2H5 nD = 1,4954 CH2=CH-CH2 \ N-isopropyl-N-allyl-dichloracetamide 3)2cH nD = 1,4921 -` / \ N-dichloroacetyl-2~2-dimethyl-1,3-0 / N-C0-CHC12 oxazolidine m.p. = 119-121 ' / \
The invention ~herefore provides a method for the selective control :
1 3 B~3B
of weeds in maize cultures, which consists in treating the seeds or the crop areas intended for the cultivation of maize in which the seeds are to ~e sown, or which have been sown, or in which the seeds have already germinated, simultaneously or successively, in optional saquence and in an appropriate interval of time, on the one hand with a herbicide, the chloroacetanilide of the formula I, and on the other with an antidote of the N,N-disubstituted dichloracetami.de of the above formula II which protects the germinated crop plants and/or the seeds thereof.
The invention is also concerned with an agent for selective control of weeds in maize, which contains as herbicidally active component the chloroacetanilide of the formula I as well as an atidote of the formula II.
~f The followil-~" ~ests were carried out to determine the selecti.ve herbicidal actinn of chloroacetanilides of the for~-nula I alone and togetheL with anti~otes of the , formula II:
Pre-emer~_nt ap~lication N-(2'-me~iloxyethyl)-2,6-dime~hy]-chloroace~an,i].ide (A) o the formula c~3 ~, ~/ C~l ~CH ~O-CH~
\~ N 2 2 J m.p. ~ 42~45 \===,~\ CO - CH 2C l was used as herbicidal active substance.
This compound was manufactured by reacting 2,6-dimethyl-aniline with methoxyacetaldehyde dissolved in benzene in the presence of trimethylamine by boiling to give 1-(2'-methoxy~ethylidene-amino)-2,6-dimethylbenzene (b.p. 58-61C/O.l Torr), converting this product by hydrogenation in ethanol with palladium-charcoal to N-(2'-methoxyethyl)-2,6-xylidine (b.p. 64C-65~C/0.2 Torr), and reacting this latter as a suspension together with potassium bicarbonate in benzene with chloroacetyl chloride.
N,N-diyllyl-dichloroacetamide (B) and N3-dichloroacetyl-2,2-dimethyl-1~3-oxyzolidine (C) were used as antido~,e, bo~h substances described in German OE~enlegungsschrift2.21$~0~7 g (Lxamples 1 and 42), as well as N-ethy'l.-N-al.lyl-dichloro-acetamide (D) and N-isopropyl--N-al].yl~dlchloroacetamide (E). Aqueous stock broths(suspenslorls) were prepared from wettable powders based on substances A, B, C, D, and E, and these suspenslons were applled 'both ~ingly and as mixtures, in the i.ndicated concentra~lons and mixture ratios, immediately after the test plants had been sown in seed dishes in a greenhouse, to the surface of t'he soil in the dishes, The seed dishes were then kept for 24 dags at 22 to 23C and 50% to 70% relative humidity while appropriately watering the dishes and the emergent plants.
The results were evaluated ater 13 and 24 days accordi.ng to a scale of rating from 1-9:
9 = plants not injured (as untreated control) 1 = plants completely withered 2 to 8 = intermediate stages of injury As test plants there were used:
crop plant: maize ("Orlea") [Zea]
weeds: Sorghum hybridum Echinochloa crus galli Setaria it.alica Digitaria sanguinalis Bromus tectorum The results are tabulated 'below, The amounts in kg/ha are in the ollowing relation to other units of measurement:
1 k~/ha = 0.1 ~/m2 _ 2 mg ~er l;tle of soil, the depth of the seed dishes i5 5 cm, so ~hat 1 m~ - 50 litres of soil.
Table I
, Herbicide A Antidote s Antidote B
amount in after 13 days after 24 days Plant kg/ha amo~mt in kg/ha amount in kg/ha 3 2 1 0,75 0,5 072! ,~ 2 1 ;0,75 0,5 0,25 . _ _ _ _ __ _ _ _ _ ~aize 0,25 9 9 9 9 0,5 ~ 9 8 9 0,75 7 9 6 9 1,0 6 9 9 5 9 9 2,0 ~ 7 8 ~ ~ 8 _ _~ _ _ __ _ _ _ ~ 9 8 9 9 9 9 9 9 Sorghum 0,25 2 2 1 2 0,5 1 2 1 1 0,75 1 1 1 1 1,0 1 1 1 1 1 2,0 1 1 1 ~ 1 1 _ _ _. _ _ _ _ _ _ crus galli 0,25 2 1 1 1 0,5 1 1 1 0,75 1 1 1 1 1,0 1 1 1 1 1 2,0 1 1 1 1 1 1 1 _ _ _ . _ _ _ _ _ __ Stealarica 0 55 1 5 1 1 1 1 7 9 1 1 2,0 1 1 1 1 1 1 1 _ _ _ _ _ _ Digitaria 0,25 1 1 1 sanguinalis 0,5 1 1 1 1 0,75 1 1 1 1 1,0 1 1 11 1 1 2,0 1 1 1 11 1 1 1 ..
- `
~ 1 6~
Table II
_ __ _ __ Herbicide A Antidote C Antidote C
amount iD after 13 days after 24 days Plant kg/ha amount kg/ha amount ln ~g~ha 0 2 l 0,75 ~0,5 0,2' 0 ~ l 0,75 0,5 0,75 _ __ ~ _ _ . _ _ _ Maize 0,25 9 9 9 9 (Orl~) 0,5 8 9 8 9 0,75 7 8 6 9 l,0 6 8 8 5 9 9 2,0 ~ 8 7 1~3 ~ 7 __ _ ~ _ l _ _ hybgrhiUdmum 0 25 2 9 9 2 2 1 9 9 2 2 ~,75 l 2 1 2 1,0 1 2 2 l 1 l 2,0 1 2 1 l l _ _ _ _ I i _ _ _ __ crus galli 0 25 2 l 1 1 l 0,75 1 1 1 l ~ . 1,0 1 1 1 1 1 1 2 0 1 1 l l l l l 1 _ ~ _ ~ _ I _ _ _ _ italica o,255 1 1 l 1 1 l 0,75 1 1 l l 1,0 1 1 1 1 1 1 _ 2,0 1 1 1 1 l l 1 .
Digitaria o 255 1 1 1 1 1 0,75 l l l l 1,0 1 1 1 1 1 1 2,0 1 ~ ~ l l 1 ~ l ---' ~- ~. .
I
$ 8 ~
Table II~
Pl.ant ~lerbicide A ¦ An~ldote D Antidote E
.~mount in 1 after 24 days after 24 c1ays kg/ha amoun~ in kg/ha amount in kg/ha O 21 l1 0,5 O 2 ~. 10.5 . ~ __. _~ I . ~.. ~ ~ ___ _ ~
O 9 9 g 9 9 9 ~ 9 l~aize 0,5 8 9 5 9 ~ 9 9 9 ~Orla) l,O 3 9 9 9 3 9 9 9 2,0 2 9 9 2 9 ~
~ ~ _ ~ __ ____ ___ _ __ .____ ___ O 9 9 9 ~ 9 9 9 9 Sorghum 0,5 2 2 2 2 2 2 2 l hybridum 1 0 2 21 2 2 21 21 21 2 . . __ _ _ ___~ _ ~___.
Echinochloa 0,5 l 1. l l l l l crus galli l,O l l l l l l l 2,0 l l l ~. l l _~ . _ __ _ ~
Setaria 0,5 2 l l l 2 l l italica l,O l l l 1 l l 1.
2,0 l l l l l l ~
_ _ _ _. _.__ . _ __ . __ __ : . O 9 9 9 9 9 9 9 9 Digitaria 0,5 l l l l l l l . 1,0 1 1 1 1 ' 1 1 1 sanguinalis 2,0 l l l l l 1.
_~ _ __ . _ ___ _ __ ~.
0,5 2 2 2 2 2 2 2 1 2 Bromus tectorum l,O l 2 l . l l l 2 1 l .~ . 2,0 l l l ~ 1 l l ___._~_ _ _ _ _ ___~
~ .
-,:
; . , , , , . .. ., . ., ....... .~ . ~.. . . ........ . . .. . . .. . . ... . ~
~ .
.
~ ~ 168~6 The results show clearly that the crop plant maize, which is virtually completely destroyed after 13 days using a rate o application of 2 kg/ha of herbicide A alone, suffers no more injury at all even after 24 days using the same amount of herbicide together with only 1/4 the amount ~0.5 kg/ha) of the antidote B, C, D or E, whereas all weeds are just as severely injured as without the antidote. It can even be seen that better results are often obtained with the application of smaller amounts of antidote than with larger ones. No surplus of antidote is therefore necessary and the ratio of antidote to herbicide can be 1:4.
It is advisable in practice, especially in regions with low rainfall, not only to apply the agent according to the invention to the surface of the soil, but to work it into the soil before the crop plants are sown~ thus preventillg only the perhaps more soluble herbicide from pene-trating into the soil when rainfall is slight and the antidote which remains on the surface from not being sufficiently active.
In the above tests, a surface treatment of the soil alone was sufficient to prove clearly an optimum effectiveness of the antidote lCI
~.~
Claims (13)
1. A method for the selective control of weeds in maize which comprises treating the crop areas for the cultivation of maize wlth the chloroacetanilide herbicide N- (2'-methoxyethyl) -2,6-dimethyl-chloracetanilide of formula I
( I ) and with an antidote selected from the group of N,N-disubstituted dichloracetamidec corresponding to the formula II
(II) wherein R1 and R2 are individually allyl or lower alkyl radicals or together with the nitrogen atom form the 1,3-oxazolidine ring, which optionally may be substituted by methyl radicals, said antidote being present in a concentration of from about 0,01 to 1 part by weight per part by weight of said chloracetanilide.
( I ) and with an antidote selected from the group of N,N-disubstituted dichloracetamidec corresponding to the formula II
(II) wherein R1 and R2 are individually allyl or lower alkyl radicals or together with the nitrogen atom form the 1,3-oxazolidine ring, which optionally may be substituted by methyl radicals, said antidote being present in a concentration of from about 0,01 to 1 part by weight per part by weight of said chloracetanilide.
2. A method according to claim 1 which consists in applying the active substance of the formula I and the antidote of the formula II to the crop area before the sowing of the seeds.
3. A method according to claim 1, which consits in treating the crop area intended for sowing with the antidote of the formula II, then sowing, and after the seeds have been sown and the plants have emerged, applying the herbicide of the formula I,
4. A method according to claim 1, which consists in using as antidote of the formula II N,N-diallyl-dichloracetamide.
5. A method according to claim 1, which consists in using as antidote of the formula II N-allyl-N-ethyl-dichlor-acetamide.
6. A method according to claim 1, which consists in using as antidote of the formula II N-allyl-N-isopropyl-dichloracetamide.
7. A method according to claim 1, which consists in using as antidote of the formula II 2,2-dimethyl-3-dichlor-acetyl-1,3-oxazolidine.
8. A selective herbicidal composition for controlling weeds in maize, which in addition to a suitable carrier contains as herbicidally active component the chloracetanilide of the formula I of claim 1 and, as protective antidote for maize a N,N-disubstituted chloracetamide of formula II, of claim 1, said antidote being present in a concentration of from about 0.01 to 1 part by weight per part by weight of said chloracetanilide.
9. The composition according to claim 8, which contains as antidote a N,N-disubstituted dichloracetamide according to formula II.
10. The composition according to claim 8, which contains as antidote N,N-diallyl-dichloracetamide.
11. The composition according to claim 8, which contains as antidote N-allyl-N-ethyl-dichloracetamide.
12. The composition according to claim 8, which contains as antidote N-allyl-N-isopropyl-dichloracetamide.
13. The composition according to claim 8, which contains as antidote 2,2-dimethyl-3-dichloracetyl-1,3-oxazolidine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1083/73 | 1973-01-25 | ||
| CH108373A CH574207A5 (en) | 1973-01-25 | 1973-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1168886A true CA1168886A (en) | 1984-06-12 |
Family
ID=4202057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000190455A Expired CA1168886A (en) | 1973-01-25 | 1974-01-18 | Method and agent for selective control of weeds in corn |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS49102837A (en) |
| CA (1) | CA1168886A (en) |
| CH (1) | CH574207A5 (en) |
| DE (1) | DE2402983A1 (en) |
| FR (1) | FR2215170B1 (en) |
| GB (1) | GB1454043A (en) |
| IL (1) | IL44050A (en) |
| IT (1) | IT1049212B (en) |
| SU (1) | SU582740A3 (en) |
| ZA (1) | ZA74507B (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053297A (en) * | 1975-04-21 | 1977-10-11 | Velsicol Chemical Corporation | Selective herbicidal compositions |
| IT1079199B (en) * | 1976-10-29 | 1985-05-08 | Montedison Spa | ANTIDOTES, OF THE CLASS OF DICHLOROACETAMIDES PARTICULARLY ACTIVE IN PROTECTING MAIZE FROM TOXIC ACTION EXERCISED BY GLYCINE ESTERS N, N SUBSTITUTED HERBICIDE AND HERBICIDE ASSOCIATION FOR MAIZE CULTURES |
| IT1114195B (en) * | 1977-12-23 | 1986-01-27 | Montedison Spa | TWO DICHLOROACETAMIDE ANTIDUCTS FOR NON-SELECTIVE HERBICIDES PARTICULARLY ACTIVE TO PROTECT THE MAIZE FROM TOXIC ACTION EXERCISED BY GLYCIN ESTERS N, N HERBICIDES REPLACED |
| JPS5762205A (en) * | 1977-07-07 | 1982-04-15 | Stauffer Chemical Co | Herbicidal composition for rice fields |
| CH640108A5 (en) * | 1978-02-06 | 1983-12-30 | Nitrokemia Ipartelepek | WEED KILLERS. |
| US4260410A (en) * | 1978-03-31 | 1981-04-07 | Chevron Research Company | Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes |
| US4174210A (en) * | 1978-03-31 | 1979-11-13 | Chevron Research Company | Herbicidal and plant-growth regulating N-haloacetylphenylamino carbonyl oximes |
| DE2828303A1 (en) * | 1978-06-28 | 1980-01-17 | Bayer Ag | USE OF N, N-DIALLYL DICHLORACETAMIDE FOR IMPROVING THE CROP PLANT TOLERABILITY OF HERBICIDE-ACTIVE ACETANILIDES |
| DE2832046A1 (en) * | 1978-07-21 | 1980-01-31 | Basf Ag | HERBICIDES BASED ON ACETANILIDES |
| GR66644B (en) * | 1978-07-27 | 1981-04-03 | Basf Ag | |
| DE2832950A1 (en) * | 1978-07-27 | 1980-02-21 | Basf Ag | HERBICIDAL AGENTS |
| DE2832940A1 (en) * | 1978-07-27 | 1980-02-14 | Basf Ag | HERBICIDAL AGENTS |
| US4261733A (en) * | 1978-11-30 | 1981-04-14 | Monsanto Company | Herbicidal compounds and method of preparation and use |
| US4249935A (en) | 1979-07-12 | 1981-02-10 | Basf Aktiengesellschaft | Herbicidal agents |
| DE2930448A1 (en) * | 1979-07-26 | 1981-02-26 | Bayer Ag | COUNTERPROTECTOR FOR THE PROTECTION OF CULTURAL PLANTS FROM HERBICIDE DAMAGE |
| US4606759A (en) * | 1980-03-25 | 1986-08-19 | Monsanto Company | Herbicidal 2-haloacetanilides |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| BR8206082A (en) * | 1981-10-20 | 1983-09-13 | Sipcam | SELECTIVE HERBICIDE COMPOSITION FOR MAIZE AND SORGHUM, PROCESS FOR MANUFACTURING AND PROCESS FOR APPLICATION |
| US4505738A (en) * | 1982-05-10 | 1985-03-19 | Ciba-Geigy Corporation | Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides |
| HU193171B (en) * | 1983-07-21 | 1987-08-28 | Eszakmagyar Vegyimuevek | Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote |
| US4734119A (en) | 1983-11-15 | 1988-03-29 | Ciba-Geigy Corporation | Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides |
| US4618361A (en) * | 1983-12-12 | 1986-10-21 | Ciba-Geigy Corporation | Acylamides and compositions for the protection of cultivated plants against the phytotoxic action of herbicides |
| ZA853997B (en) * | 1984-05-28 | 1986-01-29 | Ciba Geigy Ag | Composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides |
| US5215570A (en) * | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| LT3943B (en) | 1993-12-23 | 1996-05-27 | Ciba Geigy Ag | Remedy for cultured plants protection, use of sulphamoyl-phenyl-carbamides for cultured plant protection, herbicidal preparation, process for preparing sulphamoyl-phenyl-carbamides |
| CN111807984A (en) * | 2020-07-19 | 2020-10-23 | 江苏云帆化工有限公司 | Novel synthetic process of dimethachlor |
| CN113979880A (en) * | 2021-11-15 | 2022-01-28 | 上海农帆生物科技有限公司 | Novel method for preparing dimethachlor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US4033756A (en) * | 1971-09-17 | 1977-07-05 | Gulf Research & Development Company | Dichloroacetamide treated rice seeds |
-
1973
- 1973-01-25 CH CH108373A patent/CH574207A5/xx not_active IP Right Cessation
-
1974
- 1974-01-18 CA CA000190455A patent/CA1168886A/en not_active Expired
- 1974-01-18 IT IT19576/74A patent/IT1049212B/en active
- 1974-01-21 IL IL44050A patent/IL44050A/en unknown
- 1974-01-22 DE DE2402983A patent/DE2402983A1/en active Pending
- 1974-01-23 SU SU7401989303A patent/SU582740A3/en active
- 1974-01-23 FR FR7402197A patent/FR2215170B1/fr not_active Expired
- 1974-01-24 GB GB329374A patent/GB1454043A/en not_active Expired
- 1974-01-24 ZA ZA740507A patent/ZA74507B/en unknown
- 1974-01-25 JP JP49011351A patent/JPS49102837A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH574207A5 (en) | 1976-04-15 |
| DE2402983A1 (en) | 1974-08-01 |
| ZA74507B (en) | 1974-12-24 |
| JPS49102837A (en) | 1974-09-28 |
| FR2215170A1 (en) | 1974-08-23 |
| IL44050A0 (en) | 1974-05-16 |
| IT1049212B (en) | 1981-01-20 |
| GB1454043A (en) | 1976-10-27 |
| SU582740A3 (en) | 1977-11-30 |
| FR2215170B1 (en) | 1976-11-19 |
| IL44050A (en) | 1977-02-28 |
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