CA1243856A - Herbicidal agent - Google Patents
Herbicidal agentInfo
- Publication number
- CA1243856A CA1243856A CA000480242A CA480242A CA1243856A CA 1243856 A CA1243856 A CA 1243856A CA 000480242 A CA000480242 A CA 000480242A CA 480242 A CA480242 A CA 480242A CA 1243856 A CA1243856 A CA 1243856A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- phenyl
- compound
- octyl
- active
- 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
Links
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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
Abstract
ABSTRACT
Synergistic herbicidal agent containing, as the active constituent, a mixture of 0-[3-phenyl-6-chloro-pyridazin-4-yl] S-(n-octyl) thiocarbonate, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine and a chloro-acetamie, and its use.
Synergistic herbicidal agent containing, as the active constituent, a mixture of 0-[3-phenyl-6-chloro-pyridazin-4-yl] S-(n-octyl) thiocarbonate, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine and a chloro-acetamie, and its use.
Description
~L~3f~56 Herbici~al agen~
The Application relates to a synergistic herbi-cidal agent containing~ as the active constituent~ a mix-ture o~ O-C3-phenyL-6~chloro~pyridazin 4~yl~ S~(n-octyl~
thiocarbona~e~ 2-chloro-4-e~hylamino 6~isopropylamino-193,5-triazine and a chloroacetamide.
It is known from US Patent Speci~ication 3,953~445 that 3-phenyl-6 halogeno-pyridazinyl thiocarbonates and dithiocarbonat~s have herbicidal proper~ies and are suitable, inter alia~ for combating sensitive grasses in the juvenile stage of plant developmentO In practice, in particular~ the co~pound 0~3-phenyl-6-chloro~pyrid-azin 4-yl~ S-(n-octyl) thiocar~onate tpyridate) has proved itself as 3 herbicidal agentr However, it has been foun~
tnat certain millet ~eeds which have already de~eloped ~ore than 4 leaves an~ are accor~ingly alreany in the tillering stage can no longer be satisfac~orily com~a~ed ~ith pyridate by itself~ or ~hat un~esirably high doses of active ingredient are required for complete com~a~ing.
~0 I't is kno~n from "The Pestici~e Manual"~
edition, 1979, page 22 that 2-chloro~4 ethylamino~6~iso-propylamino~1,3~5 triazine (atrazine) can be use~ as a pre~emergence and post~e~ergence herbici~e in many crops, including maize~ Ko~ever~ ~hen combating ~ilcl ~illet, for example Echinochloa crus galli~ by the pre emergence or post-emergence method, no satisfactory result is ~o be achieved (communications from the Federal Biolo ical Institute for Agriculture an~ Forestry~ Berlin-Dah~em9 19679 No~ 121, page 237 and summaries pages 238 and 239).
It is also kno~n that 2-chloroacetanilides are suita~le as pre-emergence herbicides (Weed Control Hand-book: Principles 7th Edition, 1982 by ~lack~ell Scientific Publications), and it is kno~n from the "Zeitschrif~ fur Pflanzenkrankheiten und Planzenschutz, ~Journal of Plant Diseases and Plant Protection~ special edition No. X~
1984, Verlag Eugen Ul~er Stuttgart, pages 361 to 367, in particuLar page 365, 1s~ and last paragraph~ and summaries 366 ana 367" that the action of the 2-chloroacetanilide 2 chloro-2'~6'-dimethyloN~ pyrazo~ylrnethy~)-acetaniliae ~metazachlor) together with an anti~ote is increase~ by .~æ~3~
~ 2 --the addition of atrazine~ so that in aadition ~o ~he action on ~rasses~ the action against ~eeds is also su~stantially increasedn A precondition for an action against millet is~ howeverO that i~ can be ereated in ~he pre-emergence stage~ in the 1- to 2-leaf staye or just in the germ stage. ~rom the same ~iterature referenceO pages 369 to 376, in particular page 372 an~ summaries pages 375 and 376, it is kno~n that the actisn spectru~ of the 2-chloroacetamide~ -chloroacetiG aci~ N (3~5,5-trimethyl-cyclohexen~1-yl)-N-isopropylamide (trime~achlor) is like~ise increased in combination ~i~h atrazine, the mos~
reliable combating result ~eing achieved on emergence of the maize. Such her~icidal ~ixtures in ~hich the ctions are increased additively and in ~hich ehe particular gaps in the action of th~ indivi~ual components are fille~ are cus~omary in agrotechnology.
Unexpectedly, in contrastO it has been found that in a combination o~ pyri~ate, atrazine an~ a chloroacet-amide~ the action spectra of the individual active ingredi-~0 ents are not increase~ additively~ as is to be expeceed in principle~ but the pos~emergence action of such a com~ination is particularly pronounced an~ a~vantageously has an effectO and that this action additionally is synergistic.
The possibility of post~emergence treatment means for the practice of combating weeas that the harmful grasses (wi ld mi l let~ can be destroyed in all thei r stages oAf development from emergence to the start of tillering ~y a single combating operationO ~hilst in the case of an action9 for exampleO in only the germ stage, only the part cular weeds ~hich are just germinating are destroyed, so tha~ wee~s ~hich germinate some~hat later mus~ be com-bated againl Several applications wou~ therefore be necessary.
The synergistic action means that the amounts of tne inaivi~ual components applied can be çonsidera~ly reduced for the same level of action9 and that a higher aegree o-f com~ating of wee~s is also achievea where the individual components ~ould have lost their action in the r2gion of application amounts ~hich are altogether too lo~. This results in a consi~era~le ex~ension ot the ~eed spectrum an~ an additional increase in the safety margin for the crop plan~s~ as i5 necessary an~ aesirable for unintentional overdosing of ac~ive ingredient.
The present invention accordingly relates to a herbicidal agen~ ~hich is characterise~ in ~hat it con-tains, as the active cons~ituent~ the co~pound 0-C3-phenyl-6-chloro-pyridazjn-4 yl~ S-(n~octyl) ~hiocarbonate mixea ~ith the compound 2 chloro-4-ethylamino-6-isopro-pylamino-1~3,5-triazine and a chloroacetamide of the general formula o Il ~R
cl-cH2-c -N\ tI~
in wnich R~ denotes an alkyl~ alkoxyaLkyl or pyrazol-1-yl-methyl radical and R2 denotes a phenyl, 2D6~di~
aLkylphenyl or trime~hyLryclohexenyl ra~ical, the ~er~
alkyl or alkoxy in R1 and R2 comprising 1 to 3 car~on atoms.
The synergistic herbicidal agent contains, as the active constitu~nt, a mixture of pyriaate, atrazine ana a 2-chloroacetamide~ in particular a 2-c~loroace~anilide.
Possi~le compounds of this type are, for example, ~rimexachlor, metazachlor~ alachlor (2-chloro-N-(2~6~ -diethylphenyl3-N-tmethoxymethyl)-aceta~iae)~ metolachlor (2 chloro-N-t2-ethyl-6-methylphenyl)~N-(2-methoxy-1-methylethyl)acetamide)~ azetochlor (2-chloro-N-(2-ethyl-6-methylphenyl)~N-(ethoxymethyl)acetamide) or propachlor (2-chloro-N-(1 methylethyl)-N-phenylacetamide)~
Synersistic agents which contain~ as the active constituent~ a mixture of pyrida~e, atrazine and alachlor or pyriaate~ atrazine and metolachlor are partic~larly preferre a .
The composition of the agent according to the invention can vary within a certain ranger Usually, 0.25 to 4 parts of atrazine and 0.15 to 6 parts of a chlofoacetamide are present per part of pyridate. Pre-ferably~ 0.5 to 2 parts of atra~ine and 0~3 to ?.5 par~s of a chloroacetamide are present per part of pyr1date~
The agent accorcling to the invention ~ith the ne~
active ingredient combina~ion also contains, in ad~ition to the active ingreaients mentionecl, suitable excipients and/
or other adaitives. These can ~e solid or liquid and cor-respond to the su~stances custo~ary in formulation tech-nology~ such as~ for example, natural or regenerate~
mineral substances, solvents, dispersing agents~ wetting agents, tackifying agents, thickeners, anti-foaming agents, ~inders or fertilizers. Agents ~hich r duce the ~elting point of one or more of the active ingredientts) can also be a~ded.
Suit3ble use forms are thus, for example, ~ettable powders~ directly sprayable or dilutable solutions, sus-pensions, emulsion concentrates, emulsions9 solu~le pow-ders, dUSts~ granules and also encapsulations in, for exa~pLeD polymeriç substances. The metho~s of use~ such as spraying~ mistingO dusting~ ssattering or wat~ring, are chosen according ~o the inten~e~ aims and the given circumstances~ 2S is the nature of the agents.
The formulations, that is to say the agents~ pre parations or compositions con~aining the active ingre~ient mixture according to the invention andO if appropriate~
a solia or liqui~ additive~ are prepared in a kno~n man~
ner~ for example by intimate mixing and/or grin~ing of the active ingredients ~ith extenders~ such as~ for example, ~ith solid carriers, soLvents and, if appropri-ate, surface-active compouncls (surfactants).
Solid carriers ~hich can be used, for example for wettable powdersO dispersable granules and dusts, are~
in addition to natural rock po~ders, such as bentonites, calcite, Champagne chalkO ~alc, kaolin, montmorillonite 3S or attapulgite, also synthetic substances~ such as highly disperse silicic acid or highly disperse absorbent poly-mers. Possible grained, adsorptive carriers for granules are porous types, such as, for example, pumice, brick dust, sepiolite or bentonite~ and possible non-adsorptive ~3~
~ 5 ~
carrier ma~rials areD for example, calcite or sand.
larg~ number of pre-granuLate~ materials of inorganic or organic nature can aLso be used.
Possible solvents for suspension concentrates or emulsion concen~ra~es are aroma~ic hydrocar~ons~ prefer ably C~ to C~2 fractions, such as~ for example, xylene mixtures or substitutable naphtha~enes~ phthalic aci~
esters, such as di~utyl or dioctyl phthalate~ aliphatic hydrocar~ons, such as cylcohexane or paraffins~ vegetable oils~ such as sunflo~er oil or rapesee~ oilO alcohols and glycols and ethers and esters thereof~ such as ethano~r ethylene glycol, diethylene glycol and alkyl and dialkyl ethers thereofD ke~ones, such as cyclohexanone or iso-phorone, highly polar solvents~ such as N~methyl-2-pyrro lidone, dimethyl sulfo~i~e or climethylformamide~ ana optionally epoxi~ised ve~etable oils; or ~ater.
PossiblP agents ~hich have the effect of lowering the m~lting point are all the a~ents ~hich, on the basis of cryostatic measurements, are suieable for ~his pur-~0 pose~ such as~ for example, camphor~ naphthalene~ nitro-benzene~ dimethyl sulfoxide an~ acetophenone.
Possible surface-active compounds are non-ionic~
cationic and/or anionic surfactants ~ith good emulsifying, dispersing and ~etting properties. Surfactants are also to be understood as meaning surfactant mixtures~
Suita~le anionic surfactants can be either so-called water-solu~le soaps or water-soluble synthetic surface-active compounds.
Soaps ~hich may be mentioned are the alkali metal, 3û alkaLine earth metal or optionaLly su~stituted ammonium salts of hi0her fatty aci~s (C10 to C22), such as, for exampLe, the Na or K salts of oleic or stearic aci~, or of naturally occ~rring fatty acid mixtures, ~hich can be obtained~ for example, from coconut oil or ~allo~ oil.
The fatty acid methyl-taurine salts may furthermore also bs mentionedq However, so called synthetic surfac~an~s are more frequent~y use~9 in particular fatty sulfonates~ fatty sulfates, sulfonatecl benzimidazole derivatives or ~3;~
,s ' alkylarylsulfona~es~
The fatty suLfona~es or sulfates are as a rule presPnt in ehe for~ of alkali meeal~ alkaline earth metaL
or optionally substi~u~ed ammonium sal~s an~ have an alkyl radical with 8 to 22 C atoms, alkyL also including the alkyl part of acyl ra~icals~ for example the Na or Ca salt of ligninsulfonic acid~ of dodecylsulfuric aci~
ester or of a faety alcoho~ sulfa~e mixture prepared from naturally occurring fatty acids. Thes~ also include the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts~ The suLfonated benzimid-azole deriva~ives preferably contain 2-sulfonic acid groups ana a fatty acid radical ~ith 8 to 22 C a~omsO
Alkylarylsulfonates are, for example~ the Na, Ca or tri ethanolamine salts of dodecylbenzenesulfonic aci~, of dibutylnaphthalenesulfonic acid or o-f a naphthalenesul-fonic acid/formaldehyde condensation product.
It is furthermore also possible ~o use correspon~-ing phosphatesO such as, for ex~mple, sa~ts of the phos~
The Application relates to a synergistic herbi-cidal agent containing~ as the active constituent~ a mix-ture o~ O-C3-phenyL-6~chloro~pyridazin 4~yl~ S~(n-octyl~
thiocarbona~e~ 2-chloro-4-e~hylamino 6~isopropylamino-193,5-triazine and a chloroacetamide.
It is known from US Patent Speci~ication 3,953~445 that 3-phenyl-6 halogeno-pyridazinyl thiocarbonates and dithiocarbonat~s have herbicidal proper~ies and are suitable, inter alia~ for combating sensitive grasses in the juvenile stage of plant developmentO In practice, in particular~ the co~pound 0~3-phenyl-6-chloro~pyrid-azin 4-yl~ S-(n-octyl) thiocar~onate tpyridate) has proved itself as 3 herbicidal agentr However, it has been foun~
tnat certain millet ~eeds which have already de~eloped ~ore than 4 leaves an~ are accor~ingly alreany in the tillering stage can no longer be satisfac~orily com~a~ed ~ith pyridate by itself~ or ~hat un~esirably high doses of active ingredient are required for complete com~a~ing.
~0 I't is kno~n from "The Pestici~e Manual"~
edition, 1979, page 22 that 2-chloro~4 ethylamino~6~iso-propylamino~1,3~5 triazine (atrazine) can be use~ as a pre~emergence and post~e~ergence herbici~e in many crops, including maize~ Ko~ever~ ~hen combating ~ilcl ~illet, for example Echinochloa crus galli~ by the pre emergence or post-emergence method, no satisfactory result is ~o be achieved (communications from the Federal Biolo ical Institute for Agriculture an~ Forestry~ Berlin-Dah~em9 19679 No~ 121, page 237 and summaries pages 238 and 239).
It is also kno~n that 2-chloroacetanilides are suita~le as pre-emergence herbicides (Weed Control Hand-book: Principles 7th Edition, 1982 by ~lack~ell Scientific Publications), and it is kno~n from the "Zeitschrif~ fur Pflanzenkrankheiten und Planzenschutz, ~Journal of Plant Diseases and Plant Protection~ special edition No. X~
1984, Verlag Eugen Ul~er Stuttgart, pages 361 to 367, in particuLar page 365, 1s~ and last paragraph~ and summaries 366 ana 367" that the action of the 2-chloroacetanilide 2 chloro-2'~6'-dimethyloN~ pyrazo~ylrnethy~)-acetaniliae ~metazachlor) together with an anti~ote is increase~ by .~æ~3~
~ 2 --the addition of atrazine~ so that in aadition ~o ~he action on ~rasses~ the action against ~eeds is also su~stantially increasedn A precondition for an action against millet is~ howeverO that i~ can be ereated in ~he pre-emergence stage~ in the 1- to 2-leaf staye or just in the germ stage. ~rom the same ~iterature referenceO pages 369 to 376, in particular page 372 an~ summaries pages 375 and 376, it is kno~n that the actisn spectru~ of the 2-chloroacetamide~ -chloroacetiG aci~ N (3~5,5-trimethyl-cyclohexen~1-yl)-N-isopropylamide (trime~achlor) is like~ise increased in combination ~i~h atrazine, the mos~
reliable combating result ~eing achieved on emergence of the maize. Such her~icidal ~ixtures in ~hich the ctions are increased additively and in ~hich ehe particular gaps in the action of th~ indivi~ual components are fille~ are cus~omary in agrotechnology.
Unexpectedly, in contrastO it has been found that in a combination o~ pyri~ate, atrazine an~ a chloroacet-amide~ the action spectra of the individual active ingredi-~0 ents are not increase~ additively~ as is to be expeceed in principle~ but the pos~emergence action of such a com~ination is particularly pronounced an~ a~vantageously has an effectO and that this action additionally is synergistic.
The possibility of post~emergence treatment means for the practice of combating weeas that the harmful grasses (wi ld mi l let~ can be destroyed in all thei r stages oAf development from emergence to the start of tillering ~y a single combating operationO ~hilst in the case of an action9 for exampleO in only the germ stage, only the part cular weeds ~hich are just germinating are destroyed, so tha~ wee~s ~hich germinate some~hat later mus~ be com-bated againl Several applications wou~ therefore be necessary.
The synergistic action means that the amounts of tne inaivi~ual components applied can be çonsidera~ly reduced for the same level of action9 and that a higher aegree o-f com~ating of wee~s is also achievea where the individual components ~ould have lost their action in the r2gion of application amounts ~hich are altogether too lo~. This results in a consi~era~le ex~ension ot the ~eed spectrum an~ an additional increase in the safety margin for the crop plan~s~ as i5 necessary an~ aesirable for unintentional overdosing of ac~ive ingredient.
The present invention accordingly relates to a herbicidal agen~ ~hich is characterise~ in ~hat it con-tains, as the active cons~ituent~ the co~pound 0-C3-phenyl-6-chloro-pyridazjn-4 yl~ S-(n~octyl) ~hiocarbonate mixea ~ith the compound 2 chloro-4-ethylamino-6-isopro-pylamino-1~3,5-triazine and a chloroacetamide of the general formula o Il ~R
cl-cH2-c -N\ tI~
in wnich R~ denotes an alkyl~ alkoxyaLkyl or pyrazol-1-yl-methyl radical and R2 denotes a phenyl, 2D6~di~
aLkylphenyl or trime~hyLryclohexenyl ra~ical, the ~er~
alkyl or alkoxy in R1 and R2 comprising 1 to 3 car~on atoms.
The synergistic herbicidal agent contains, as the active constitu~nt, a mixture of pyriaate, atrazine ana a 2-chloroacetamide~ in particular a 2-c~loroace~anilide.
Possi~le compounds of this type are, for example, ~rimexachlor, metazachlor~ alachlor (2-chloro-N-(2~6~ -diethylphenyl3-N-tmethoxymethyl)-aceta~iae)~ metolachlor (2 chloro-N-t2-ethyl-6-methylphenyl)~N-(2-methoxy-1-methylethyl)acetamide)~ azetochlor (2-chloro-N-(2-ethyl-6-methylphenyl)~N-(ethoxymethyl)acetamide) or propachlor (2-chloro-N-(1 methylethyl)-N-phenylacetamide)~
Synersistic agents which contain~ as the active constituent~ a mixture of pyrida~e, atrazine and alachlor or pyriaate~ atrazine and metolachlor are partic~larly preferre a .
The composition of the agent according to the invention can vary within a certain ranger Usually, 0.25 to 4 parts of atrazine and 0.15 to 6 parts of a chlofoacetamide are present per part of pyridate. Pre-ferably~ 0.5 to 2 parts of atra~ine and 0~3 to ?.5 par~s of a chloroacetamide are present per part of pyr1date~
The agent accorcling to the invention ~ith the ne~
active ingredient combina~ion also contains, in ad~ition to the active ingreaients mentionecl, suitable excipients and/
or other adaitives. These can ~e solid or liquid and cor-respond to the su~stances custo~ary in formulation tech-nology~ such as~ for example, natural or regenerate~
mineral substances, solvents, dispersing agents~ wetting agents, tackifying agents, thickeners, anti-foaming agents, ~inders or fertilizers. Agents ~hich r duce the ~elting point of one or more of the active ingredientts) can also be a~ded.
Suit3ble use forms are thus, for example, ~ettable powders~ directly sprayable or dilutable solutions, sus-pensions, emulsion concentrates, emulsions9 solu~le pow-ders, dUSts~ granules and also encapsulations in, for exa~pLeD polymeriç substances. The metho~s of use~ such as spraying~ mistingO dusting~ ssattering or wat~ring, are chosen according ~o the inten~e~ aims and the given circumstances~ 2S is the nature of the agents.
The formulations, that is to say the agents~ pre parations or compositions con~aining the active ingre~ient mixture according to the invention andO if appropriate~
a solia or liqui~ additive~ are prepared in a kno~n man~
ner~ for example by intimate mixing and/or grin~ing of the active ingredients ~ith extenders~ such as~ for example, ~ith solid carriers, soLvents and, if appropri-ate, surface-active compouncls (surfactants).
Solid carriers ~hich can be used, for example for wettable powdersO dispersable granules and dusts, are~
in addition to natural rock po~ders, such as bentonites, calcite, Champagne chalkO ~alc, kaolin, montmorillonite 3S or attapulgite, also synthetic substances~ such as highly disperse silicic acid or highly disperse absorbent poly-mers. Possible grained, adsorptive carriers for granules are porous types, such as, for example, pumice, brick dust, sepiolite or bentonite~ and possible non-adsorptive ~3~
~ 5 ~
carrier ma~rials areD for example, calcite or sand.
larg~ number of pre-granuLate~ materials of inorganic or organic nature can aLso be used.
Possible solvents for suspension concentrates or emulsion concen~ra~es are aroma~ic hydrocar~ons~ prefer ably C~ to C~2 fractions, such as~ for example, xylene mixtures or substitutable naphtha~enes~ phthalic aci~
esters, such as di~utyl or dioctyl phthalate~ aliphatic hydrocar~ons, such as cylcohexane or paraffins~ vegetable oils~ such as sunflo~er oil or rapesee~ oilO alcohols and glycols and ethers and esters thereof~ such as ethano~r ethylene glycol, diethylene glycol and alkyl and dialkyl ethers thereofD ke~ones, such as cyclohexanone or iso-phorone, highly polar solvents~ such as N~methyl-2-pyrro lidone, dimethyl sulfo~i~e or climethylformamide~ ana optionally epoxi~ised ve~etable oils; or ~ater.
PossiblP agents ~hich have the effect of lowering the m~lting point are all the a~ents ~hich, on the basis of cryostatic measurements, are suieable for ~his pur-~0 pose~ such as~ for example, camphor~ naphthalene~ nitro-benzene~ dimethyl sulfoxide an~ acetophenone.
Possible surface-active compounds are non-ionic~
cationic and/or anionic surfactants ~ith good emulsifying, dispersing and ~etting properties. Surfactants are also to be understood as meaning surfactant mixtures~
Suita~le anionic surfactants can be either so-called water-solu~le soaps or water-soluble synthetic surface-active compounds.
Soaps ~hich may be mentioned are the alkali metal, 3û alkaLine earth metal or optionaLly su~stituted ammonium salts of hi0her fatty aci~s (C10 to C22), such as, for exampLe, the Na or K salts of oleic or stearic aci~, or of naturally occ~rring fatty acid mixtures, ~hich can be obtained~ for example, from coconut oil or ~allo~ oil.
The fatty acid methyl-taurine salts may furthermore also bs mentionedq However, so called synthetic surfac~an~s are more frequent~y use~9 in particular fatty sulfonates~ fatty sulfates, sulfonatecl benzimidazole derivatives or ~3;~
,s ' alkylarylsulfona~es~
The fatty suLfona~es or sulfates are as a rule presPnt in ehe for~ of alkali meeal~ alkaline earth metaL
or optionally substi~u~ed ammonium sal~s an~ have an alkyl radical with 8 to 22 C atoms, alkyL also including the alkyl part of acyl ra~icals~ for example the Na or Ca salt of ligninsulfonic acid~ of dodecylsulfuric aci~
ester or of a faety alcoho~ sulfa~e mixture prepared from naturally occurring fatty acids. Thes~ also include the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts~ The suLfonated benzimid-azole deriva~ives preferably contain 2-sulfonic acid groups ana a fatty acid radical ~ith 8 to 22 C a~omsO
Alkylarylsulfonates are, for example~ the Na, Ca or tri ethanolamine salts of dodecylbenzenesulfonic aci~, of dibutylnaphthalenesulfonic acid or o-f a naphthalenesul-fonic acid/formaldehyde condensation product.
It is furthermore also possible ~o use correspon~-ing phosphatesO such as, for ex~mple, sa~ts of the phos~
2~ phoric asi~ ester of a p nonylphenol-(4 14)~ethylene oxi~e adductl Pocsi~le non-ionic surfactants are~ a~ove all, polyglycol e~her derivatives of aliphatic or cycloali-phatic alcohols, saturated or unsaturate~ fatty acids and alkylphenols~ ~hich may con~ain 3 to 30 glycol eeher groups and 8 to 20 carbon atoms in the talipha~ic) hydro carbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
Other suitable non-ionic surfactants are the water-soluble polyethylene oxide adducts on polypropylene glycol, ethylenediaminepolypropylene glycol and alkyl-polypropylene glycol with 1 to 10 carbon atoms in the alkyl chain, the adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
Examples which may be mentioned of non-ionic sur-factan~s are nonylphenol polyethoxyethanols, castor oil polyglycol e~hers, polypropylene/polyethyLene oxide ~3~
a~ucts~ tri~utylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanDl.
Fatty acid esters of polyoxy~hyLene sorbi~an, such as polyoxyethylene sorbitan trioleate~ are further-5 more also possible..
The cationic surfactants are, aboYe all, qua~er-nary ammonium salts ~hich contain at least one alkyl radi-cal ~ith 8 to 22 C atoms as N-substi~uents and lower op~ionaLly halogenated alkyl~ benzyl or lo~er hydroxy-alkyl radical~ as further substituents. The salts arepreferably present in the for~ of halides, methyl-sulfates or ethyl-sulfates, for example seearyltrime~hylammonium chlori~e or ~enzyLdi(2-chloroethyl)ethylammonium bromide~
The surfac~ants customary in formuLation techno-lo3y are described, inter alia, in the following pu~
cations: "McCutcheon's Detergents and Emulsifiers Annual"
MC Publishing Corp., Ringwood, New Jersey, 1979 and Sisely and Wood, "Encyclopedia of Surface Active Agen~s", Chemical Publishing Co.~ Xncl New York, 1964.
The active ingredient content in commercial agents is bet~een 0.1 and 95 per cent ~y weigh~, preferably between 1 and 80 per cent by weight.
The active ingredients pyridate and atra2ine are usually added in an application a~ount of 0.5 to 2 kg/haD
25 prefera~ly in an amount of 0O75 to 1.5 kg/ha, ana the active ingredients of the chloroace~amide type are usu-ally added in an application amount of 0.3 to 3 kg/ha9 preferably in an amount of 0.5 to 2 kgtha~ The total application amount of active substance in the synergistic 30 agent is 1.3 to 5.0 kg/ha, preferably 2 to 3.5 kg~ha.
The synergistic agent is used by the post-emergence methodu Its ~ain field of use is maize crops.
However~ it can also be used in permanent crops, such as fruit orchar~s and vineyards, or in other plantation crops~ and for totaL combating of wee~s on areas which are not used agriculturally, such as on indus~rial or railway landD
The herbicidal agent exhibits a synergistic effect.
To calcuLate such a synergistic effect, it is assumed 5~
that a p~rely additive effect is calc~lated from ~he fol-lo~in3 formula:
E = X ~ y ~ X x r S (accor~ing eo L~E. Limpel et al.~ 1962, Wee~ control by di-methyl tetrachloro~erephthalate alone and in certain combin~
ations. Proc.NE~CC 16: 48-53, ~ased on DJP. Gowing, 1960, Comments on tests of herbicide mixtures~ ~eeds 8r 379-391~u E = the degree of herbici~al action (X ~estruction) to be expected (in the case of additive ac~ion) after appli-cation of A ~ B in an amount of p ~ q kg/ha~
X ~ degree of action ~%) on application of the active ingre~ient A at p kg/haO
Y = degree o~ action (X) on ap~lication of the active ingreaient B a~ q kg/ha~
The above formula ~as extended by Colby SCalcula-tion Synergistic and Antagonistic Responses of Her~icide Combinations, ~eeds~ 15, 20~ to the effect that 3^
component ~ix~ures can also ~e investigate~ for any synergis~ic actions~
The degree of action to be expected from a mix-~ure of three components is accordingly calculatPd by the follo~ing formula ~X x Y + X x Z ~ Y ~ Z~ X ~s ~ x E ~ X ~ r ~
If the degree of action found experimentally for the component mixture is above the value of E calcula~ed accor~ing to the above formulae~ synergism exists, and if the value is less than E, antagonism is present.
Example 1:
Active ingre~ient 1 (tec'nical grade atrazine) 10.20%
Active ingredient 2 (technical grade alachlor) 22.00%
Active ingredient 3 (technical grade pyridate) 13.90X
35 Technical gra~e camphor 3.65X
Na ~ibutylnaphthalenesulfonate2.50X
Na oleylmethyltauri~e 5.00~
Champagn~ chalk 6.25X
Highly disperse silicic acid36.50%
~ 31~56 _ 9 _ A homogeneous solution was prepared from active ingre~ients 2 and 3 and technical gra~e camphor~ with gentle var~ing.
A pow~er ~as prepars~ from active ingredient 1 and the remaining additives in a suitable mixer and the solution defined a~ove ~as sprayed onto the powder -with the stirrer s~itched on. When ~he spraying opera tion had ended, the co~ponents ~ere nixed intensively for a~out a fur~her 15 minutes and then ground via a pin ~isc mill. A spray liquor which can be used for application can be prepared using the ~etta~le po~der prepared in this manner.
Example 2:
Active ingredient 1 ttechnical grade atrazine) 12.75%
Active ingredien~ 3 (technical grade pyridate) 12.50X
Artive ingredient 4 ~technical grade metolachlor) 2~00X
Teshnical gra~e camphor 3.~5X
Na dibutyLnaphthaleneswlfonate2.50X
Na oleylmethyltauri ae 5 . oo%
Z0 Champagne chalk ~.25%
Highly d1sperse precipitated silicic acia 31.35X
The formulation ~as prepared as in Example 1 except that active ingredients 3 an~ 4 were no~ use~
instea~ of ac~ive ingredients ~ and 3.
Example 3:
~ xperimen~al areas which ~ere cultiva~ed with maize and ~hich~ by application of chlorotriazines for several years, were unilaterally and heavily contaminated by the gramineous weeas Echinochloa crus galli (cockspur grass~ and Setaria viridis ~green panic grass) ~ere divided into 25 m2 plots. In each case t~o plots were provided per experimental !~roduc~ or pro~uct combina~ion.
As soon as the harmful grasses were mostly in the 3-leaf stage to the tillerin0 stageO the active ingredients or ac~ive ingredient com~inations listed ~elo~ were applied to the experimental plots in the form of water-dispersible formulations~ A plot spraying apparatus operatea with compressed air was usea for tne application. The pro-ducts were tnereby applied wi~h an amount of wa~er
Other suitable non-ionic surfactants are the water-soluble polyethylene oxide adducts on polypropylene glycol, ethylenediaminepolypropylene glycol and alkyl-polypropylene glycol with 1 to 10 carbon atoms in the alkyl chain, the adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
Examples which may be mentioned of non-ionic sur-factan~s are nonylphenol polyethoxyethanols, castor oil polyglycol e~hers, polypropylene/polyethyLene oxide ~3~
a~ucts~ tri~utylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanDl.
Fatty acid esters of polyoxy~hyLene sorbi~an, such as polyoxyethylene sorbitan trioleate~ are further-5 more also possible..
The cationic surfactants are, aboYe all, qua~er-nary ammonium salts ~hich contain at least one alkyl radi-cal ~ith 8 to 22 C atoms as N-substi~uents and lower op~ionaLly halogenated alkyl~ benzyl or lo~er hydroxy-alkyl radical~ as further substituents. The salts arepreferably present in the for~ of halides, methyl-sulfates or ethyl-sulfates, for example seearyltrime~hylammonium chlori~e or ~enzyLdi(2-chloroethyl)ethylammonium bromide~
The surfac~ants customary in formuLation techno-lo3y are described, inter alia, in the following pu~
cations: "McCutcheon's Detergents and Emulsifiers Annual"
MC Publishing Corp., Ringwood, New Jersey, 1979 and Sisely and Wood, "Encyclopedia of Surface Active Agen~s", Chemical Publishing Co.~ Xncl New York, 1964.
The active ingredient content in commercial agents is bet~een 0.1 and 95 per cent ~y weigh~, preferably between 1 and 80 per cent by weight.
The active ingredients pyridate and atra2ine are usually added in an application a~ount of 0.5 to 2 kg/haD
25 prefera~ly in an amount of 0O75 to 1.5 kg/ha, ana the active ingredients of the chloroace~amide type are usu-ally added in an application amount of 0.3 to 3 kg/ha9 preferably in an amount of 0.5 to 2 kgtha~ The total application amount of active substance in the synergistic 30 agent is 1.3 to 5.0 kg/ha, preferably 2 to 3.5 kg~ha.
The synergistic agent is used by the post-emergence methodu Its ~ain field of use is maize crops.
However~ it can also be used in permanent crops, such as fruit orchar~s and vineyards, or in other plantation crops~ and for totaL combating of wee~s on areas which are not used agriculturally, such as on indus~rial or railway landD
The herbicidal agent exhibits a synergistic effect.
To calcuLate such a synergistic effect, it is assumed 5~
that a p~rely additive effect is calc~lated from ~he fol-lo~in3 formula:
E = X ~ y ~ X x r S (accor~ing eo L~E. Limpel et al.~ 1962, Wee~ control by di-methyl tetrachloro~erephthalate alone and in certain combin~
ations. Proc.NE~CC 16: 48-53, ~ased on DJP. Gowing, 1960, Comments on tests of herbicide mixtures~ ~eeds 8r 379-391~u E = the degree of herbici~al action (X ~estruction) to be expected (in the case of additive ac~ion) after appli-cation of A ~ B in an amount of p ~ q kg/ha~
X ~ degree of action ~%) on application of the active ingre~ient A at p kg/haO
Y = degree o~ action (X) on ap~lication of the active ingreaient B a~ q kg/ha~
The above formula ~as extended by Colby SCalcula-tion Synergistic and Antagonistic Responses of Her~icide Combinations, ~eeds~ 15, 20~ to the effect that 3^
component ~ix~ures can also ~e investigate~ for any synergis~ic actions~
The degree of action to be expected from a mix-~ure of three components is accordingly calculatPd by the follo~ing formula ~X x Y + X x Z ~ Y ~ Z~ X ~s ~ x E ~ X ~ r ~
If the degree of action found experimentally for the component mixture is above the value of E calcula~ed accor~ing to the above formulae~ synergism exists, and if the value is less than E, antagonism is present.
Example 1:
Active ingre~ient 1 (tec'nical grade atrazine) 10.20%
Active ingredient 2 (technical grade alachlor) 22.00%
Active ingredient 3 (technical grade pyridate) 13.90X
35 Technical gra~e camphor 3.65X
Na ~ibutylnaphthalenesulfonate2.50X
Na oleylmethyltauri~e 5.00~
Champagn~ chalk 6.25X
Highly disperse silicic acid36.50%
~ 31~56 _ 9 _ A homogeneous solution was prepared from active ingre~ients 2 and 3 and technical gra~e camphor~ with gentle var~ing.
A pow~er ~as prepars~ from active ingredient 1 and the remaining additives in a suitable mixer and the solution defined a~ove ~as sprayed onto the powder -with the stirrer s~itched on. When ~he spraying opera tion had ended, the co~ponents ~ere nixed intensively for a~out a fur~her 15 minutes and then ground via a pin ~isc mill. A spray liquor which can be used for application can be prepared using the ~etta~le po~der prepared in this manner.
Example 2:
Active ingredient 1 ttechnical grade atrazine) 12.75%
Active ingredien~ 3 (technical grade pyridate) 12.50X
Artive ingredient 4 ~technical grade metolachlor) 2~00X
Teshnical gra~e camphor 3.~5X
Na dibutyLnaphthaleneswlfonate2.50X
Na oleylmethyltauri ae 5 . oo%
Z0 Champagne chalk ~.25%
Highly d1sperse precipitated silicic acia 31.35X
The formulation ~as prepared as in Example 1 except that active ingredients 3 an~ 4 were no~ use~
instea~ of ac~ive ingredients ~ and 3.
Example 3:
~ xperimen~al areas which ~ere cultiva~ed with maize and ~hich~ by application of chlorotriazines for several years, were unilaterally and heavily contaminated by the gramineous weeas Echinochloa crus galli (cockspur grass~ and Setaria viridis ~green panic grass) ~ere divided into 25 m2 plots. In each case t~o plots were provided per experimental !~roduc~ or pro~uct combina~ion.
As soon as the harmful grasses were mostly in the 3-leaf stage to the tillerin0 stageO the active ingredients or ac~ive ingredient com~inations listed ~elo~ were applied to the experimental plots in the form of water-dispersible formulations~ A plot spraying apparatus operatea with compressed air was usea for tne application. The pro-ducts were tnereby applied wi~h an amount of wa~er
3~
C Q rrespon~ing ~o 400 l~ha.
The experiment was evaluated by first aeterminin3 ~he quaneity of harmful grasses in the untreate~ part areas b~/ counting the plan~ den~ity on in each case
C Q rrespon~ing ~o 400 l~ha.
The experiment was evaluated by first aeterminin3 ~he quaneity of harmful grasses in the untreate~ part areas b~/ counting the plan~ den~ity on in each case
4 x 0.25 m2 part areas in duplicate ~accordingly 8 x 0~25 m2 2 m2 per experimental member~. This value ~as set a~ 1QOX as a reference parameter. 8y similar deter~inations of the quanti~y of grasses in the particu-lar plots treated with the products or product com~ina-tions listed, the residual contamination with gramineous~eeds was determined and was re.ated to the value for the control plots9 and the ~egree of her~icidal ac~ion was thus determineC~ The experi~ental pro~ram was carried out on a total of 7 experimental sites.
The values ~ere subjected to analysis in accor~
~ance with the method of Limpel and Colby to calculate any synergistic effectsu ` " ~2~315 5~
Ta~le 1 Degree of herbicidal ac~ion (% destruction) of Ech i noch Loa c rus ga l L i NoO Active 3 of found calc.~iffer~
ingredient~s) ai/ha ence At razi ne1~01D0 65 Alachlor10680 6 - -3 Pyrida~e 900 60 4 Metolachlor1~980 15 - -+ 2 1, 000 ~70 67 ~3 1 ~ 68 0 1 ~ 3 1~000 ~85 86 -1 9~0 2 ~ 3 ~ ~680 +65 62 ~3 1 ~ 2 ~ 3 1~000 +100 37+13 1 ~680 1 ~ 4 1,000 +74 70 ~4 1 ~980 3 ~ 4 900 ~63 66 -3 1 , 9 80 1 ~ 3 ~ 4 1~000 +99 88~11 1 ~980 ~ ~3~
- ~2 -Exampl~ 4:
As ~escribe~ in Example l, experi~ental areas ~ere again discov2re~ on ~hich chiefly wil~ milL2t of the genus Digitaria ~D. sanguinalis, common finger grass) haa been se~ectione~ ~y applic3tion of chloro~riazine for several years.
The experimental procedure ana al50 the method of evaluation are the same as those describe~ in Example 1.
Ta~le 2 Degree of herbiciaal action (X ~estruceion3 of Digitaria sanguinalis No. Active g of found calc. ~iffer-ingredients(s)ai/ha ence 1 Atrazine 1,000 10* - -15 2 AlachLor 1,680 25 - -3 Pyri~ate 900 45 - -1 ~ 2 1~000 + 37 33 +4 1~680 1 ~ 3 1~000 ~ 53 51 ~2 Z ~ 3 1~680 + 55 59 -4 1 ~ 2 + 31,000 ~ 10063 ~37 1~680 *) Digitar~3 sanguinalis is known to be insensitive ~resistant) towar~ a~razine.
The values ~ere subjected to analysis in accor~
~ance with the method of Limpel and Colby to calculate any synergistic effectsu ` " ~2~315 5~
Ta~le 1 Degree of herbicidal ac~ion (% destruction) of Ech i noch Loa c rus ga l L i NoO Active 3 of found calc.~iffer~
ingredient~s) ai/ha ence At razi ne1~01D0 65 Alachlor10680 6 - -3 Pyrida~e 900 60 4 Metolachlor1~980 15 - -+ 2 1, 000 ~70 67 ~3 1 ~ 68 0 1 ~ 3 1~000 ~85 86 -1 9~0 2 ~ 3 ~ ~680 +65 62 ~3 1 ~ 2 ~ 3 1~000 +100 37+13 1 ~680 1 ~ 4 1,000 +74 70 ~4 1 ~980 3 ~ 4 900 ~63 66 -3 1 , 9 80 1 ~ 3 ~ 4 1~000 +99 88~11 1 ~980 ~ ~3~
- ~2 -Exampl~ 4:
As ~escribe~ in Example l, experi~ental areas ~ere again discov2re~ on ~hich chiefly wil~ milL2t of the genus Digitaria ~D. sanguinalis, common finger grass) haa been se~ectione~ ~y applic3tion of chloro~riazine for several years.
The experimental procedure ana al50 the method of evaluation are the same as those describe~ in Example 1.
Ta~le 2 Degree of herbiciaal action (X ~estruceion3 of Digitaria sanguinalis No. Active g of found calc. ~iffer-ingredients(s)ai/ha ence 1 Atrazine 1,000 10* - -15 2 AlachLor 1,680 25 - -3 Pyri~ate 900 45 - -1 ~ 2 1~000 + 37 33 +4 1~680 1 ~ 3 1~000 ~ 53 51 ~2 Z ~ 3 1~680 + 55 59 -4 1 ~ 2 + 31,000 ~ 10063 ~37 1~680 *) Digitar~3 sanguinalis is known to be insensitive ~resistant) towar~ a~razine.
Claims (6)
1. Herbicidal agent, characterised in that it contains, as the active constituent, the compound 0-(3-phenyl-6-chloro-pyridazin-4-yl)S-(n-octyl)thiocarbonate mixed with 0,25 to 4 parts of the compound 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine and 0,15 - 6 parts of a chloroacetamide of the general formula (I) in which R1 denotes an alkyl, alkoxyalkyl or pyrazol-1-yl-methyl radical and R2 denotes a phenyl, 2,6-dialkylphenyl or trimethylcyclohexenyl radical, the term alkyl or alkoxy in R1 and R2 comprising 1 to 3 carbon atoms, per part of 0-(3-phenyl-6-chloropyridazin-4-yl)S-(n-octyl).
2. Herbicidal agent according to claim 1, characterised in that it contains, as the active constituent, the compound 0-(3-phenyl-6-chloro-pyridazin-4-yl)S-(n-octyl) thiocarbonate mixed with the compound 2-chloro-4-ethylamino-6-isopropyl-amino-1,3,5-triazine and the chloroacetamide 2-chloro-N-(2,6-diethylphenyl)-N
(methoxymethyl)-acetamide.
(methoxymethyl)-acetamide.
3. Herbicidal agent according to claim 1, characterised in that it contains, as the active constituent, the compound 0-(3-phenyl-6-chloro-pyridazin-4-yl)S-(n-octyl) thiocarbonate mixed with the compound 2-chloro-4-ethylamino-6-isopropyl-amino-1,3,5-triazine and the chloroacetamide 2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methylethyl)-acetamide.
4. Method of combating weeds and harmful grasses in areas which are used or not used agriculturally, characterised in that, after emergence of the plants, the areas are treated with an agent according to claim 1 in application amounts which correspond to 1,3 to 5,0 kg/ha, preferably 2 to 3,5 kg of active substance per hectare.
5. Method according to claim 4, characterised in that maize crops are treated with the agent mentioned.
6. Method according to claim 4, characterised in that maize crops which contain wild millet of the genus Digtaria and Echinochloa as harmful grasses are treated with the agents mentioned.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843419050 DE3419050A1 (en) | 1984-05-22 | 1984-05-22 | HERBICIDAL AGENT |
| DEP3419050.3 | 1984-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1243856A true CA1243856A (en) | 1988-11-01 |
Family
ID=6236562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000480242A Expired CA1243856A (en) | 1984-05-22 | 1985-04-26 | Herbicidal agent |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0165393B1 (en) |
| AT (1) | ATE38310T1 (en) |
| BG (1) | BG60892B1 (en) |
| CA (1) | CA1243856A (en) |
| CS (1) | CS250685B2 (en) |
| DE (2) | DE3419050A1 (en) |
| DK (1) | DK165155C (en) |
| GR (1) | GR850957B (en) |
| HU (1) | HU198610B (en) |
| PL (1) | PL142819B1 (en) |
| PT (1) | PT80490B (en) |
| RO (1) | RO91411A (en) |
| SU (1) | SU1382391A3 (en) |
| ZA (1) | ZA853842B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006202047B2 (en) * | 1995-04-12 | 2009-04-09 | Syngenta Participations Ag | Synergistic herbicidal compositions of metolachlor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH668530A5 (en) * | 1986-10-22 | 1989-01-13 | Ciba Geigy Ag | SYNERGISTIC AGENT AND METHOD FOR SELECTIVELY WEED CONTROL IN RICE. |
| AT401994B (en) * | 1994-07-25 | 1997-01-27 | Sandoz Ag | CONCENTRATED STABLE SUSPENSION OF HERBICIDE 1,3,5-TRIAZINE AND PYRIDATE |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA847250A (en) * | 1970-07-21 | M. Lebaron Homer | Weed killing compositions and use thereof | |
| NL157008B (en) * | 1966-02-01 | 1978-06-15 | Monsanto Co | PROCESS FOR PREPARING A PREPARATION WITH PHYTOTOXIC ACTION, FORMED PREPARATIONS WITH THIS ACTION, AND PROCEDURE FOR PREPARING N-DIG-SUBSTITUTED ALPHA-CHLORACETAMIDE DERIVATIVES. |
| US3547620A (en) * | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| NL144477B (en) * | 1970-04-15 | 1975-01-15 | Monsanto Co | PROCESS FOR PREPARING A GRAIN-SHAPED PREPARATION WITH HERBICIDE EFFECT. |
| DD112988A5 (en) * | 1972-06-06 | 1975-05-12 | ||
| DE2331398C3 (en) * | 1973-06-20 | 1979-10-11 | Lentia Gmbh | Esters of S-PhenyM-hydroxy-e-halopyridazine compounds, their preparation and herbicidal compositions containing them |
| DE2351553A1 (en) * | 1973-10-13 | 1975-04-24 | Basf Ag | (Non)selective synergistic herbicide - contg. two or more of triazine; benzothiadiazinone dioxide, benzonitrile, phenoxy - carboxylic acid, dinitrophenol, benzaldoxime aryl ether |
| DE2648008C3 (en) * | 1976-10-23 | 1980-09-04 | Basf Ag, 6700 Ludwigshafen | Acetanilide |
| DE2704281A1 (en) * | 1977-02-02 | 1978-08-03 | Bayer Ag | Herbicidal N-heterocyclyl-methyl-halo-acetanilide derivs. - prepd. from a N-halomethyl-chloro:acetanilide and a heterocycle |
| AT357818B (en) * | 1978-09-29 | 1979-12-15 | Chemie Linz Ag | HERBICIDAL AGENT |
| DE2856651A1 (en) * | 1978-12-29 | 1980-07-10 | Huels Chemische Werke Ag | N-Tri:methyl-cycloalkenyl-acetamide derivs. - useful as selective herbicides and plant growth regulators |
| US4411692A (en) * | 1981-03-26 | 1983-10-25 | Monsanto Company | Flowable herbicides |
| US4461641A (en) * | 1982-02-25 | 1984-07-24 | Ciba-Geigy Corporation | Herbicidal mixtures |
-
1984
- 1984-05-22 DE DE19843419050 patent/DE3419050A1/en not_active Withdrawn
-
1985
- 1985-04-10 EP EP85104337A patent/EP0165393B1/en not_active Expired
- 1985-04-10 AT AT85104337T patent/ATE38310T1/en not_active IP Right Cessation
- 1985-04-10 DE DE8585104337T patent/DE3565928D1/en not_active Expired
- 1985-04-22 GR GR850957A patent/GR850957B/el unknown
- 1985-04-26 CA CA000480242A patent/CA1243856A/en not_active Expired
- 1985-05-06 SU SU853886704A patent/SU1382391A3/en active
- 1985-05-17 RO RO85118781A patent/RO91411A/en unknown
- 1985-05-20 CS CS853604A patent/CS250685B2/en unknown
- 1985-05-20 PT PT80490A patent/PT80490B/en not_active IP Right Cessation
- 1985-05-20 PL PL1985253496A patent/PL142819B1/en unknown
- 1985-05-21 ZA ZA853842A patent/ZA853842B/en unknown
- 1985-05-21 BG BG70355A patent/BG60892B1/en unknown
- 1985-05-21 HU HU851919A patent/HU198610B/en not_active IP Right Cessation
- 1985-05-21 DK DK223885A patent/DK165155C/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006202047B2 (en) * | 1995-04-12 | 2009-04-09 | Syngenta Participations Ag | Synergistic herbicidal compositions of metolachlor |
| AU2006202047B9 (en) * | 1995-04-12 | 2009-04-23 | Syngenta Participations Ag | Synergistic herbicidal compositions of metolachlor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3565928D1 (en) | 1988-12-08 |
| ZA853842B (en) | 1986-01-29 |
| GR850957B (en) | 1985-05-08 |
| PL142819B1 (en) | 1987-12-31 |
| HU198610B (en) | 1989-11-28 |
| ATE38310T1 (en) | 1988-11-15 |
| BG60892B1 (en) | 1996-06-28 |
| EP0165393B1 (en) | 1988-11-02 |
| CS250685B2 (en) | 1987-05-14 |
| RO91411A (en) | 1987-04-30 |
| PT80490B (en) | 1987-09-30 |
| DE3419050A1 (en) | 1985-11-28 |
| DK165155B (en) | 1992-10-19 |
| SU1382391A3 (en) | 1988-03-15 |
| EP0165393A1 (en) | 1985-12-27 |
| DK223885D0 (en) | 1985-05-21 |
| HUT37862A (en) | 1986-03-28 |
| DK165155C (en) | 1993-03-01 |
| DK223885A (en) | 1985-11-23 |
| PL253496A1 (en) | 1986-05-20 |
| PT80490A (en) | 1985-06-01 |
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