IT8222549A1 - Herbicidal compounds derived from phenoxybenzoic acids - Google Patents
Herbicidal compounds derived from phenoxybenzoic acids Download PDFInfo
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- IT8222549A1 IT8222549A1 IT1982A22549A IT2254982A IT8222549A1 IT 8222549 A1 IT8222549 A1 IT 8222549A1 IT 1982A22549 A IT1982A22549 A IT 1982A22549A IT 2254982 A IT2254982 A IT 2254982A IT 8222549 A1 IT8222549 A1 IT 8222549A1
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- 150000001875 compounds Chemical class 0.000 title claims description 40
- 230000002363 herbicidal effect Effects 0.000 title claims description 9
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 title description 5
- 239000013543 active substance Substances 0.000 claims description 52
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- 125000005843 halogen group Chemical group 0.000 claims description 9
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 229930195733 hydrocarbon Natural products 0.000 claims description 5
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- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- SUZXWXGJCOCMHU-UHFFFAOYSA-N n-sulfonylbenzamide Chemical compound O=S(=O)=NC(=O)C1=CC=CC=C1 SUZXWXGJCOCMHU-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 235000002252 panizo Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
D E S C R I Z I O N E DESCRIPTION
dell ' invenzione industriale dal titolo: of the industrial invention entitled:
"Composti erbicidi derivati da acidi fenossibenzoici" "Herbicidal compounds derived from phenoxybenzoic acids"
R I A S S U N T O SUMMARY
Nuovo erbicida per cereali oppure per soia avente la formula New herbicide for cereals or for soy having the formula
nella quale: in which:
? Y1 ? un atomo di azoto oppure ? un gruppo -CH=, ? ? ? un atomo di azoto oppure ? un gruppo -CX 4, quest'ultima possibilit? realizzandosi soltanto quando Y1 ? un gruppo -CH=, ? Y1? a nitrogen atom or? a group -CH =,? ? ? a nitrogen atom or? a group -CX 4, the latter possibility? realizing only when Y1? a group -CH =,
? X2 identici oppure diversi, rappresentano un atomo di alogeno oppure un gruppo polialogenoalchile, un gruppo ciano, un nitro-gruppo, alchile, alcossile, alchilsolfonile, -S02NH2, un nitroso-gruppo, un gruppo di un-carbossilato di alchile ? X2 identical or different, represent a halogen atom or a polyhalogenoalkyl group, a cyano group, a nitro-group, alkyl, alkoxy, alkylsulfonyl, -S02NH2, a nitro-group, an alkyl-carboxylate group
- X4 ? l?atomo di idrogeno oppure ha uno dei significati indicati per x1 fino ? X3. - X4? the hydrogen atom or does it have one of the meanings indicated for x1 up to? X3.
- Y ? un gruppo ossidrile oppure ? un atomo di alogeno - Y? a hydroxyl group or? a halogen atom
- E ? un radicale di un idrocarburo, sostituito oppure non sostituito, oppure ? un eterociclo sostituito oppure non sostituito* - AND ? a radical of a hydrocarbon, substituted or unsubstituted, or? a substituted or unsubstituted heterocycle *
D E S C R I Z I O N E DESCRIPTION
La presente invenzione riguarda erbicidi selettivi, della famiglia degli acidi fenossibenzoici, e riguarda andhe il loro procedimento di preparazione e la loro applicazione. The present invention relates to selective herbicides, of the phenoxybenzoic acid family, and relates to their preparation process and their application.
Si conoscono erbicidi derivati dall?acido fenossibenzoico e pi? in particolare dall'acido Are herbicides derived from phenoxybenzoic acid and pi? especially from acid
5-[ 2?cloro-4? (trifluororaetil)fenossi]?nitrobenzoico noto con il nome di acifluorfen* 5- [2? Chlorine-4? (trifluororaethyl) phenoxy]? nitrobenzoic known as acifluorfen *
Sono stati gi? proposti diversi derivati di questi composti ivi compresi gli esteri di alchile, di cicloalchile, di tioalchile, di fenile, le ammidi monoSichilate oppure diai chilate, i cloruri di acido* Tra i brevetti americani che descrivono tali composti si possono citare i brevetti US 3652 645, 3 784 635, 3 873 302, 3983 168, 3 907 866, 3798 276, 3928 416, 4 063 929. Were they already? various derivatives of these compounds are proposed including alkyl, cycloalkyl, thioalkyl, phenyl esters, monoSichylated or diaicated amides, acid chlorides. , 3 784 635, 3 873 302, 3983 168, 3 907 866, 3798 276, 3928 416, 4 063 929.
La denominazione chimica dei prodotti nella presente descrizione viene effettuata secondo la nomenclatura francese, ma adottando la numerazione delle posizioni dei sostituenti secondo la nomenclatura anglosassone ( numero posto davanti al nome del sostituente). The chemical name of the products in this description is carried out according to the French nomenclature, but adopting the numbering of the positions of the substituents according to the Anglo-Saxon nomenclature (number placed in front of the name of the substituent).
Nonostante il notevole numero di derivati di acidi fenossibenzoici che esistono, anche semplici difenil-eteri, ? augurabile poter disporre ancora di altri erbicidi di questi gruppi in modo da poter risolvere tutti i casi possobili di trattamento di erbicidi desiderabili, in particol?re in fase di pre-emer genza. Despite the considerable number of phenoxybenzoic acid derivatives that exist, even simple diphenyl ethers,? It is desirable to have still other herbicides of these groups available so as to be able to solve all the possible cases of treatment of desirable herbicides, in particular in the pre-emergence phase.
Nella presente descrizione, si adottano i termini di pre-sollevamento e pre emergenza come sinonimi e i termini di post-sollevamento e post-emergenza come sinonimi. In the present description, the terms pre-lift and pre-emergence are used as synonyms and the terms post-lift and post-emergence as synonyms.
La presente invenzione ha dunque per oggetto nuovi composti erbicidi di formula: The present invention therefore relates to new herbicidal compounds having the formula:
nella quale: in which:
- Y1 ? un atomo di azoto oppiare ? un gruppo -CH=, - Y1? an opiate nitrogen atom? a group -CH =,
- Y2 ? un atomo di azoto oppure ? un gruppo ~CX4=, quest*ultima possibilit? manifestandosi soltanto quando Y1 ? un gruppo ~CH=, - Y2? a nitrogen atom or? a group ~ CX4 =, this * last possibility? manifesting only when Y1? a group ~ CH =,
? X1, X2, X3, identici oppure diversi, rappresentano un ?tomo di alogeno, (in particolare cloro, bromo, oppure fluoro), un gruppo polialogenoalchile in particolare trifluorometile, un gruppo -CN oppure un nitro gruppo, un gruppo alchile, alcossile, S02 alchile, SO2NH, nitroso-gruppo carbossilato di alchile, la parte alchilica di questi radicali avendo preferibilmente da 1 a 4 atomi di carbonio, ? X1, X2, X3, identical or different, represent a? Tome of halogen, (in particular chlorine, bromine, or fluorine), a polyhalogenoalkyl group in particular trifluoromethyl, a -CN group or a nitro group, an alkyl group, alkoxy, S02 alkyl, SO2NH, nitro-alkyl carboxylate group, the alkyl part of these radicals preferably having 1 to 4 carbon atoms,
? ?4 ha i medesimi significati indicati per X1 fino a X2 e pu? essere, inoltre, 1*atomo di idrogeno, ? ? 4 has the same meanings indicated for X1 to X2 and can? also be 1 * hydrogen atom,
? R ? un radicale di un idrocarburo, sostituito, oppure non sostituito, avente in generale da 1 a ? R? a radical of a hydrocarbon, substituted or unsubstituted, generally having from 1 to
12 atomi di carbonio, in particolare un radicale alchile oppure arile, sostituito oppure non sostituito, oppure un radicale eterociclico sostituito oppure non sostituito, avente da 5 a 7 atomi di carbonio nel. -ciclo, 12 carbon atoms, in particular a substituted or unsubstituted alkyl or aryl radical, or a substituted or unsubstituted heterocyclic radical, having from 5 to 7 carbon atoms in the. -cycle,
- Y ? un gruppo ossidrile oppure ? un atomo di alogeno, preferibilmente cloro. - Y? a hydroxyl group or? a halogen atom, preferably chlorine.
Come esempi di radicali R, si possono citare in particolare i radicali alchile avente da 1 a 4 atomi di carbonio; i radicali arile, in particolare fenile, non sostituiti oppure sostituiti con da 1 a 4 radicali alchili aventi ciascuno da 1 a 4 atomi di carbonio oppure con atomi di cloro o di bromo, oppure con gruppi ossidrili, SH, CN, COOH, oppure con gruppi alcossile,tioalchile, carbossilato di alchile, le porzioni alchiliche di questi radicali avendo da 1 a 4 atomi di carbonio nella parte alchilica; i gruppi alchenile e alchinile avendo da 2 a 6 atomi di carbonio* As examples of R radicals, alkyl radicals having from 1 to 4 carbon atoms can be mentioned in particular; the aryl radicals, in particular phenyl, unsubstituted or substituted with from 1 to 4 alkyl radicals each having from 1 to 4 carbon atoms or with chlorine or bromine atoms, or with hydroxyl groups, SH, CN, COOH, or with alkoxy, thioalkyl, alkyl carboxylate groups, the alkyl portions of these radicals having from 1 to 4 carbon atoms in the alkyl part; the alkenyl and alkynyl groups having from 2 to 6 carbon atoms *
Tra i composti di formula (i), una classe da tutto particolarmente vantaggiosa ? rappresentata dai composti nei quali X1 e X2 sono gruppi di polialogeno alchile oppure sono atomi di alogeno, Y1 e Y sono il gruppo -CH-, X- ? il nitro?gruppo oppure ? un atomo di alogeno Pi? in particolare si preferis i composti nei quali X1 ? CF3, X2 ? Cl, X3 ? Gl oppure N?2 Y e Y2 sono -CH=. Among the compounds of formula (i), a particularly advantageous class? represented by compounds in which X1 and X2 are polyhalogen alkyl groups or are halogen atoms, Y1 and Y are the -CH-, X-? the nitro? group or? a halogen atom Pi? in particular we prefer the compounds in which X1? CF3, X2? Cl, X3? Gl or N? 2 Y and Y2 are -CH =.
Si tratta dunque in particolare di composti di formula: It is therefore in particular of compounds of the formula:
In questi composti, si preferiscono parimenti quelli per i quali R ? un gruppo alchile e Y ? un atomo di cloro. In these compounds, those for which R? an alkyl group and Y? an atom of chlorine.
Su un piano abbastanza generale, i composti secondo la presente invenzione possono venire pi? spesso preparati partendo da precursori di formula: On a fairly general level, the compounds according to the present invention can come more? often prepared starting from formula precursors:
nella quale Y<? >? 1<?>atomo di idrogeno oppure ? un atomo di un metallo alcalino, preferibilmente sodio, gli altri simboli avendo i diversi significati gi? indicati sopra. in which Y <? >? 1 <?> Hydrogen atom or? an atom of an alkali metal, preferably sodium, the other symbols having the different meanings already? indicated above.
La maggior parte dei composti di formula (III), oppure loro omologhi diretti, sono gi? descritti nelle domande di brevetti europee No.,3416 oppure 23392. Most of the compounds of formula (III), or their direct homologs, are already? described in European patent applications No., 3416 or 23392.
I composti secondo la presente invenzione nei quali ? ? un atomo di alogeno si preparano facilmente mediante reazione di un ipoalogenito su un precursore di formula (III) nella qule Y*, ? un atomo di idrogeno. The compounds according to the present invention in which? ? a halogen atom are easily prepared by reaction of a hypohalogen on a precursor of formula (III) in qule Y *,? a hydrogen atom.
Si effettua la reazione in generale in;<' >soluzione oppure in sospensione acquosa o idroorganica, in pres?nza di un solvente miscibile con acqua coma alcooli oppure chetoni, in particolare metanolo, etanolo,:.,acetone, metiletilchetone, metilisobutilchetone. Si effettua la reazione pi? spesso tra -10?C e * 6o?C, preferibilmente tra 10 e 40?C, la concentrazione del mezzo di reazione in reattivo di formula (ili) e in prodotto di formula (i) secondo l'invenzione essendo compresa tra 0,5% in peso e 30% in peso, preferibilmente tra 2% e 10%; la quantit? di ipoalogenito impiegata in generale ? compresa tra una volta e tre volte la quantit? stechiometrica* Il pH, nel corso della reazione in generale/superiore a 10, preferibilmente superiore a 11,5. The reaction is generally carried out in a solution or in aqueous or hydroorganic suspension, in the presence of a solvent miscible with water such as alcohols or ketones, in particular methanol, ethanol, acetone, methylethylketone, methylisobutylketone. Is the reaction pi? often between -10 ° C and * 6 ° C, preferably between 10 and 40 ° C, the concentration of the reaction medium in the reactive of formula (IIi) and in the product of formula (I) according to the invention being comprised between 0, 5% by weight and 30% by weight, preferably between 2% and 10%; the quantity? of hypohalite used in general? between once and three times the quantity? stoichiometric * The pH, during the reaction in general / higher than 10, preferably higher than 11.5.
I composti secondo la presente invenzione nei quali Y ? un gruppo ossidrile vengono preparati in generale secondo lo schema di reazione che segue The compounds according to the present invention in which Y? a hydroxyl group are generally prepared according to the following reaction scheme
nel quale il simbolo Ar rappresenta il radicale: in which the symbol Ar represents the radical:
La prima di queste reazioni viene effettuata . vantaggiosamente in presenza diun accettore di acido come le ammine terziarie, in particolare la piridina The first of these reactions is carried out. advantageously in the presence of an acid acceptor such as tertiary amines, in particular pyridine
La seconda di queste reazioni che ? ima alcooli? si viene effettuata mediante azione di un alcoolato alcalino ( oppure-di un idrossido alcalino in soluzione in un alcool indicato con R1 OH nello schema) quindi mediante azione di un acido forte come 1*acido cloridrico. The second of these reactions which? ima alcohols? it is carried out by the action of an alkaline alcoholate (or of an alkaline hydroxide in solution in an alcohol indicated with R1 OH in the diagram) then by the action of a strong acid such as hydrochloric acid.
I composti secondo l?invenzione sono particolarmente vantaggiosi a causa della loro selettivit?, e anche a causa della loro attivit? erbicida in fase di pre-emergenza e in fase di post-emergenza. Tra le colture suscettibili di venire trattate con i prodotti dell?invenzione si possono citare soia, cotone, riso, arachide, cereali, ivi compreso il mais. The compounds according to the invention are particularly advantageous because of their selectivity, and also because of their activity. herbicide in the pre-emergence and in the post-emergence phase. Among the crops which can be treated with the products of the invention, soybeans, cotton, rice, peanuts, cereals, including corn, can be mentioned.
Alcuni esempi indicati qui di seguito a titolo non limitativo illustrano la presente invenzione e mostrano come essa pu? venire realizzata in pratica# Esempio 1: In 20 cm di soluzione acquosa di ipoclorito di sodio che titola 1,5 moli/litro d'ipoclo? rito, e contenente soda in modo che il pH sia uguale a 12, si sciolgono 0,5 g di 5-[2,4-diclorofenossil?-?2-nitro-N-metansolfonil benzammide (punto di fusione : 181?C#)# si sottopone ad agitazione per 30 minuti a 20?C. si aggiunge acido acetico goccia a goccia fino a che si raggiunge un pH di 7,5; si prosegue quindi l?agitazione ancora per 30 minuti# Some examples indicated below by way of non-limitative illustrate the present invention and show how it can? to be carried out in practice # Example 1: In 20 cm of aqueous sodium hypochlorite solution that titrates 1.5 moles / liter of hypochlorus? rite, and containing soda so that the pH is equal to 12, dissolve 0.5 g of 5- [2,4-dichlorophenoxyl? -? 2-nitro-N-methanesulfonyl benzamide (melting point: 181? C #) # is stirred for 30 minutes at 20 ° C. acetic acid is added drop by drop until a pH of 7.5 is reached; stirring is then continued for another 30 minutes #
Si filtra, si lava il precipitato con acqua fredda e si essica all'aria; si ottengono 0,3 g di 5-[2,4-diclorofenossi ]-2-nitro-N-cloro-N-me tansolfonil benzammide con punto di fusione di 161-163?C e di formula: It is filtered, the precipitate is washed with cold water and dried in the air; 0.3 g of 5- [2,4-dichlorophenoxy] -2-nitro-N-chloro-N-m and tansulfonyl benzamide are obtained with a melting point of 161-163? C and of formula:
Questo composto comporta una banda di assorbimento nell' infrarosso a 1728 cm?1 (banda del carbonile^ mentre la banda corrispondente sul reattivo di parten-?1 This compound involves an absorption band in the infrared at 1728 cm? 1 (carbonyl band ^ while the corresponding band on the starting reagent? 1
za ? a 1688 cm' ? za? to 1688 cm '?
Esempio 2 : In 10 litri di acqua si aggiungono 4,46 litri di candeggina ' contenenti 1,57 moli/Litro di ipoclorito di sodio e 105 mi di NaoH al 30% in peso in modo che il pH sia uguale a 12,2, Example 2: 4.46 liters of bleach containing 1.57 moles / liter of sodium hypochlorite and 105 ml of NaoH at 30% by weight are added to 10 liters of water so that the pH is equal to 12.2,
Si aggiungono progressivamente a 18?20?C, sotto agitazione e in 1 ora e 45 minuti, 438 g di 5-[2-clor o-4? (trifluorometil)fenossi]-2-nitro-If-metan solfo? nil?benzammide avente un punto di fusione di 215-218?C e avente la formula: 438 g of 5- [2-chlor o-4? (trifluoromethyl) phenoxy] -2-nitro-If-methane sulfur? nyl? benzamide having a melting point of 215-218? C and having the formula:
Si prosegue l?agitazione per 4 ore The stirring is continued for 4 hours
Si neutralizza quindi aggiungendo progressivamente in 20 minuti 215 mi di acido acetico e mantenendo la temperatura a 18?20?C* It is then neutralized by gradually adding 215 ml of acetic acid over 20 minutes and maintaining the temperature at 18-20 ° C *
Si filtra il precipitato bianco, lo si lava con acqua, lo si asciuga e lo si essica sotto vuoto in presenza di P2?5? si ottengono 279 g di 5-[2-cloro?4-(triflurometil )fenossi]-2-ni tro-N-cloro?It-metan solfonilbenzammide che fonde a 161-162?C. Essa ? ricristallizzabile in una miscela etere dietilico / cloroformio e ha la formula: The white precipitate is filtered, washed with water, dried and dried under vacuum in the presence of P2? 5? 279 g of 5- [2-chloro? 4- (trifluromethyl) phenoxy] -2-ni tro-N-chloro? It-methan sulfonylbenzamide are obtained which melts at 161-162 ° C. It? recrystallizable in a diethyl ether / chloroform mixture and has the formula:
in risonanza magnetica nucleare non , presenta la banda NH e in infrarosso presenta la banda di assorbimento del carbonile a 1728 cm-1. in non-nuclear magnetic resonance, it presents the NH band and in infrared it presents the carbonyl absorption band at 1728 cm-1.
Esempio 3 Example 3
in recipienti di terracotta da 20 cm x 25 cm contenenti terra, si introducono specie di colture e di erbe infestanti in file lunghe 10 cm. in 20 cm x 25 cm terracotta containers containing earth, species of crops and weeds are introduced in 10 cm long rows.
Le specie impiegate vengono indicate nella Tabella (1). The species used are indicated in Table (1).
Il cotone, il mais, la soia e lo Xanthium vengono seminati in ragione di 4-5 grani per ogni fila. Cotton, corn, soy and Xanthium are sown at the rate of 4-5 grains per row.
Le specie pi? piccole (Abutilon, senape sf atica, amaranto, miglio di Italia e setaria verde) vengono seminate senza contare i grani, ma tuttavia in numero sufficiente per formare ulteriormente una linea fitta di pianticelle. The species pi? small ones (Abutilon, sf atica mustard, amaranth, Italian millet and green setaria) are sown without counting the grains, but nevertheless in sufficient numbers to further form a dense line of seedlings.
L?innaffiamento iniziale fino al periodo di emergenza viene effettuato al disopra della terra che ricopre i grani. The initial watering up to the emergency period is carried out above the earth that covers the grains.
Il trattamento di pre?emergenza viene effettuato meno di 1 giorno dopo la semina. The pre-emergency treatment is carried out less than 1 day after sowing.
Lo stadio desiderato di sviluppo per i trattamenti di post-emergenza di cotone, di soia, di xanthium, di abutilon, di senape selvatica e di chenopodio ? lo stadio di una foglia vera oppure di una prima foglia trsfogliata. per il mais? lo stadio desiderato ? una altezza di 7.5-10 cm, mentre per le graminacee, lo stadio desiderato ? una altezza di 2,5 cm. The desired stage of development for post-emergence treatments of cotton, soy, xanthium, abutilon, wild mustard and chenopodium? the stage of a true leaf or of a first transfoliated leaf. for corn? the desired stage? a height of 7.5-10 cm, while for the grasses, the desired stage? a height of 2.5 cm.
L'applicazione delle composizioni della presente invenzione viene effettuata mediante polverizzazione sotto una pressione di 2?5 bar (= 36 psi) in ragione di 375 litri/ettaro ( = 40 galloni/acro)? Le composizioni polverizzate erano costituite da una miscela in proporzioni in volume rispettivamente di 20 cm di acqua e 0,1% di agente tensio-attivo (miscela di etere poliossietilenico e di alchil (C6-C16 benzen solfonati alcalini)* The application of the compositions of the present invention is carried out by spraying under a pressure of 2? 5 bar (= 36 psi) at the rate of 375 liters / hectare (= 40 gallons / acre)? The pulverized compositions consisted of a mixture in volume proportions of 20 cm respectively of water and 0.1% of surfactant agent (mixture of polyoxyethylene ether and alkyl (C6-C16 alkaline benzene sulfonates) *
Dopo trattamento, si effettua l'irrigazione mediante sub-irrigazione per le pianticelle gi? spuntate dal terreno e mediante innaffiamento al di sopra dei grani che non hanno ancora dato pianticelle* After treatment, irrigation is carried out by sub-irrigation for the seedlings already? sprouted from the ground and by watering above the grains that have not yet given seedlings *
Due settimane dopo il trattamento, si effettuano misurazioni di attivit? secondo una scala da. 0% a 100%. Per le erbe infestanti questa misura indica il livello di distruzione; per le culture questa misura indica il grado di attacco o grado di fitotossicit?, il numero zero essendo attribuito a piante che pres?ntano il medesimo stato della pianta di riferimento e il numero cento essendo attribuito a vaia distruzione completa. Two weeks after the treatment, are activity measurements taken? according to a scale of. 0% to 100%. For weeds this measure indicates the level of destruction; for cultures this measure indicates the degree of attack or degree of phytotoxicity, the number zero being attributed to plants that have the same state as the reference plant and the number one hundred being attributed to various complete destruction.
perci? che riguarda i dosaggi di applicazione, la corrispondenza tra unit? del sistema metrico e unit? americane ? la seguente: why? which concerns the dosages of application, the correspondence between units? of the metric system and unit? American? the following:
La tabella (il) indica i risultati ottenuti con i composti degli Esempi 1 e 2, Table (II) indicates the results obtained with the compounds of Examples 1 and 2,
Esempio 4: Applicazione erbicida, in pre-energenza delle specie vegetali.; Example 4: Herbicidal application, in pre-energy of the plant species .;
In vasi da 9 x 9 x 9 cm riempiti di terra agricola leggera, si semina un certo numero di grani determinato in funzione della specie vegetale e della grossezza del grano* In 9 x 9 x 9 cm pots filled with light agricultural soil, a certain number of grains are sown, determined according to the plant species and the size of the grain *
Si ricoprono quindi i grani con uno strato di terra avente uno spessore di circa 3 mm* The grains are then covered with a layer of earth having a thickness of about 3 mm *
Dopo umidificazione della terra, i vasi vengono trattati mediante polverizzazione di poltiglia in quantit? corrispondente ad una dose chimica di applicazione di 500 litri/ettaro e contenente la sostanza attiva alla concentrazione desiderata. After humidification of the earth, the pots are treated by pulverizing the pulp in quantities? corresponding to a chemical application dose of 500 liters / hectare and containing the active substance at the desired concentration.
La poltiglia ? stata preparata mediante diluizione di una polvere umidificabile preparata, a sua volta,jartendo da: The mush? been prepared by diluting a humidifiable powder prepared, in turn, from:
- 500 g di sostanza attiva - 500 g of active substance
- 15 g di un alchilnaftalin solfonato di sodio - 15 g of an alkylnaphtalin sulfonate of sodium
? 50 g di metilen bis (naftalin solfonato di sodio) ? 50 g di silice ? 50 g of methylene bis (sodium naphthalene sulfonate)? 50 g of silica
? 390 g di caolino ? 390 g of kaolin
A seconda della concentrazione di'sostanza attiva della poltiglia, la dose di sostanza attiva applicata ? stata di 0,25 - 2 Kg/ettaro. Depending on the concentration of active substance in the mash, the dose of active substance applied? was 0.25 - 2 kg / hectare.
I vasi trattati vengono quindi posti in vaschette destinate a ricevere l'acqua dinnaff lamento, in subirrigazione, e vengono mantenuti per 21 giorni ad una temperatura di 22?24?C con una umidit? relativa di 70%? The treated pots are then placed in trays intended to receive the water for watering, in sub-irrigation, and are kept for 21 days at a temperature of 22? 24? C with a humidity? 70% relative?
Al termine di 21 giorni, si conta il numero di piante viventi nei vasi trattati con la poltiglia che contiene la sostanza attiva da esaminare e si conta il numero di piante viventi in un vaso di riferimento trattato secondo le medesime condizioni, ma usando una poltiglia che non contiene sostanza attiva, si determina cos? la percentuale di distruzione delle piante trattate rispetto al riferimento non trattato. Una percentuale di distruzione uguale al 100% indica che si ? avuto distruzione completa della specie vegetale considerata e una percentuale di distruzione di 0% indica che il numero di piante viventi nel vaso trattato ? identico a quello nel vaso di riferimento At the end of 21 days, the number of living plants in the pots treated with the slurry containing the active substance to be examined is counted and the number of living plants in a reference pot treated under the same conditions, but using a slurry which does not contain active substance, it is determined cos? the percentage of destruction of the treated plants compared to the untreated reference. Does a destruction rate of 100% mean yes? had complete destruction of the plant species considered and a destruction percentage of 0% indicates that the number of living plants in the treated pot? identical to that in the reference vessel
Esempio 5 ; Applicazione erbicida in fase di postemergenza delle specie vegetali. Example 5; Herbicidal application in the post-emergence phase of plant species.
In vasi da 9 x 9 x 9- cm riempiti di terra agricola leggera , si semina un numero di grani determinato in funzione della specie vegetale e della grossezza del grano? In 9 x 9 x 9-cm pots filled with light agricultural soil, are you sowing a number of grains determined according to the plant species and the size of the grain?
Si ricoprono quindi i grani con uno strato di terra avente uno spessore di circa 3 mm e si lascia germogliare il grano fino a che esso fa nascere una pianticella avente un'altezza di 5-10 era. The grains are then covered with a layer of earth having a thickness of about 3 mm and the grain is allowed to sprout until it gives birth to a seedling having a height of 5-10 age.
I vasi vengono quindi trattati mediante polverizzazione di una poltiglia in quantit? corrispondente ad una dose in volume di applicazione di 500 litri/ /ettaro e contenente la sostanza attiva alla concentrazione desiderata. The jars are then treated by pulverizing a pulp in quantity? corresponding to an application volume dose of 500 liters / hectare and containing the active substance at the desired concentration.
La poltiglia ? stata preparata in modo uguale a quello descritto nell'esempio 4. The mush? was prepared in the same way as described in Example 4.
A seconda della concentrazione in sostanza attiva della poltiglia, la dose di sostanza attiva applicata ? stata di 0,125-1 Kg/ettaro# Depending on the active substance concentration of the slurry, the dose of active substance applied? state of 0.125-1 Kg / hectare #
I vasi trattati vengono quindi posti in bacinelle destinate a ricevere 1*acqua diinnaffiatura, in subirrigazione e vengono mantenuti per 14 giorni ad una temperatura di 22-24?C con una umidit? relativa di 70%. The treated pots are then placed in basins intended to receive 1 * water for irrigation, in sub-irrigation and are kept for 14 days at a temperature of 22-24 ° C with a humidity. relative of 70%.
Al termine di 14 giorni, si conta il numero di piante viventi nei vasi trattati con la poltiglia che contiene la sostanza attiva da esaminare e il numero di piante viventi in un vaso di riferimento trattato adottando le medesime condizioni , ma con una poltiche che non contiene sostanza attiva. Si determina cos? la percentuale di distruzione delle piante trattate rispetto al riferimento non trattato. Una percentuale di distruzione uguale al 100% indica che si ? avuta distruzione completa delle speie vegetale considerata e una percentuale di 0% indica che il numero di piante viventi nel vaso trattato ? identico a quello nel vaso di riferimento. At the end of 14 days, the number of living plants in the pots treated with the slurry containing the active substance to be examined and the number of living plants in a reference pot treated under the same conditions, but with a policy that does not contain, are counted. active substance. It is determined cos? the percentage of destruction of the treated plants compared to the untreated reference. Does a destruction rate of 100% mean yes? had complete destruction of the plant species considered and a percentage of 0% indicates that the number of living plants in the treated pot? identical to that in the reference vessel.
I risultati degli esempi 4 :e 5 sono indicati nella Tabella (ili). The results of examples 4: and 5 are indicated in Table (11i).
Questa tabella (III) comprende, da un lato, risultati di prei-emergenza ottenuti secondo l'esempio 4 e, d'altro canto, risultati di post-emergenza ottenuti secondo l'esempio 5? This table (III) includes, on the one hand, pre-emergence results obtained according to Example 4 and, on the other hand, post-emergence results obtained according to Example 5?
Le prove realizzate mostrano dunque le propriet? notevolmente vantaggiose dei composti secondo la presente invenzione sia nel caso di trattamenti in pre-emergenza delle colture e pi? in particolare dei The tests carried out therefore show the properties? remarkably advantageous of the compounds according to the present invention both in the case of pre-emergence treatments of the crops and more? in particular of the
della soia e/ cereali, che nel caso di trattamenti di post-emergenza in particolare della soia e dei ce- ?/ ? xng. garzano & zanarao of soy and / cereals, which in the case of post-emergency treatments in particular of soy and ce-? /? xng. garzano & zanarao
realie Nel caso della soia, l'attivit? dei colcosti ? particolarmente interesscinte quando questa coltura ? infestata da vegetali infestanti dicotiledoni? Abutilon, Xanthium e ipomea. Nel caso di cereali, l'attivit? di composti ? particolarmente interessante quando questa coltura /infestata da erbe infestanti dicotiledoni, in particolare Polygonum, Amarantus, Ambr?sia, Chrysanthenum, steliaria e Galium* realie In the case of soy, the activity? of the colcosti? particularly interesscinte when this crop? infested with dicotyledonous weeds? Abutilon, Xanthium and hypomea. In the case of cereals, the activity? of compounds? particularly interesting when this crop / infested with dicotyledonous weeds, in particular Polygonum, Amarantus, Ambr? sia, Chrysanthenum, steliaria and Galium *
Per il loro impiego pratico, i composti secondo l'invenzione vengono. impiegati raramente da soli? Pi? sovente, questi,composti fanno parte di composizioni? Queste composizioni impiegabili come agenti erbicidi, contengono come sostanza attiva un composto secondo l'invenzione come descritto precedentemente in associazione c<n supporti solidi oppure liquidi, accettabili in agricoltura e con agenti tensio-attivi parimenti accettabili in agricoltura. In particolare si possono impiegare le sostanze-veicolo inerti e usuali e gli agenti tensio-attivi usuali. Queste composizioni fanno anch'esse parte della presente invenzione? For their practical use, the compounds according to the invention are. rarely employed alone? Pi? are these compounds often part of compositions? These compositions, which can be used as herbicidal agents, contain as the active substance a compound according to the invention as described above in association with solid or liquid supports, acceptable in agriculture and with surfactant agents equally acceptable in agriculture. In particular, the inert and usual carriers and the usual surface-active agents can be used. Are these compositions also part of the present invention?
Queste composizioni possono contenere anche qualsiasi tipo di siitri ingredienti come per esempio colloidi protettori,adesivi, addensanti, agenti tixotropi, agenti di penetrazione, stabilizzanti, sequestranti, ecc,??. e anche,altre sostanze attive note dotate di propriet? pesticide ( in particolare insetticidi* fungicidi, oppure erbicidi) oppure dotati di propriet? che favoriscono la crescita delle piante (in particolare fertilizzanti) oppure dotate di propriet? che regolano la crescita delle piante? pi? in generale, i composti impiegati nella presente invenzione possono essere associati a tutti gli additivi solidi oppure liquidi secondo le tecniche usuali della realizzazione di formulazioni. These compositions can also contain any type of several ingredients such as for example protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, stabilizers, sequestrants, etc. and also, other known active substances with properties? pesticide (in particular insecticides * fungicides, or herbicides) or with properties? that favor the growth of plants (in particular fertilizers) or with properties? that regulate plant growth? pi? in general, the compounds used in the present invention can be associated with all the solid or liquid additives according to the usual techniques of making formulations.
Le dosi di impiego dei composti impiegati nella presente invenzione possono variare entro ampi limiti, in particolare a seconda della natura delle piante avventizie da eliminare e a seconda del grado di infestazione usuale delle coltura con queste piante avventizie. The doses of use of the compounds used in the present invention can vary within wide limits, in particular according to the nature of the adventitious plants to be eliminated and according to the usual degree of infestation of the crops with these adventitious plants.
In modo generale, le composizioni secondo la presente invenzione contengono usualmente da 0,05% a 95% circa (Ln peso) di una o pi? sostanze attive secondo la presente invenzione, da 1% a 95% circa di una o pi? sostanze - veicolo solide oppure liquide ed eventualmente da 0,1% a 20% circa di uno o pi? agenti tensio-attivi. Generally, the compositions according to the present invention usually contain from 0.05% to about 95% (Ln weight) of one or more? active substances according to the present invention, from about 1% to 95% of one or more? solid or liquid vehicle substances and possibly from 0.1% to about 20% of one or more? surfactant agents.
Secondo quanto ? stato gi? indicato, i composti impiegati nella presente invenzione sono generaimente associati a supporti e eventualmente a sostanze tensio?attive. In accordance to ? been already? indicated, the compounds used in the present invention are generally associated with supports and optionally with surfactant substances.
Con il termine "supporto?, nella presente descrizione, si indica una sostanza organica o minerale, naturale oppure sintetica, con la quale la sostanza attiva ? associata per facilitare la sua applicazione sulla pianta, sui grani oppure sul suolo. Questo supporto ? dunque in generale inerte e deve essere accettabile in agricoltura, in particolare sulla pianta trattata, il supporto pu? essere solido (argille, silicati naturali o sintetici, silice, resine, cere, fertilizzanti solidi, ecc.;.) oppure liquido (acqua, alcooli, in particolare butanolo; esteri, in particolare acetato di metilglicol, chetoni, in particolare cicloesanone e isoforone; frazioni di petrolio; idrocarburi aromatici in particolare xileni oppure idrocarburi paraffinici; idrocarburi clorurati alifatici, in particolare tricloroetano, oppure aromatici, in particolare clorobenzeni; solventi idrosolubili come dimetilformammide, dimetilsolfossido, N-metil?pirrolidone; gas liquefatti, ecc....)? The term "support" in the present description indicates an organic or mineral substance, natural or synthetic, with which the active substance is associated to facilitate its application on the plant, on the grains or on the soil. generally inert and must be acceptable in agriculture, in particular on the treated plant, the support can be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.;.) or liquid (water, alcohols, in particular butanol; esters, in particular methylglycol acetate, ketones, in particular cyclohexanone and isophorone; petroleum fractions; aromatic hydrocarbons in particular xylenes or paraffinic hydrocarbons; aliphatic chlorinated hydrocarbons, in particular trichloroethane, or aromatic, in particular chlorobenzenes; such as dimethylformamide, dimethyl sulfoxide, N-methyl? pyrrolidone; liquefied gases, etc ....)?
L?agente tensio-attivo pu? essere un agente emulsionante, disperdente oppure umidificante. The surfactant agent can be an emulsifying, dispersing or wetting agent.
~ del tipo ionico oppure non ionico oppure ima miscela di tali agenti tensioattivi, si possono citare per esempio sali di acidi poliacrilici, sali di acidi lignosolfonici, sali di acidi fenolsolfonici oppure naftalinsolf onici, prodotti di policondensazio? ne dell*ossido di etilene su alcooli grassi oppure su acidi grassi oppure su animine grasse, fenoli sostituiti (in particolare alchilfenoli oppure arilfe? noli), sali di esteri di acidi solfosuccinici, derivati della taurina (in particolare alchiltaurati), esteri fosforici di alcooli oppure di fenoli poliossietilati, esteri di acidi grassi.e di polioli, derivati con funzione di solfati, solfonati e fosfati dei composti precedenti. La presenza almeno di un agente tensio-attivo in generale,? indispensabile nel caso in cui la materia prima e/o il supporto inerte non siano solubili in acqua e nel caso in cui la sostanza-veicolo di applicazione sia l'acqua, ~ of the ionic or non-ionic type or a mixture of such surfactants, for example salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalinsulphonic acids, polycondensation products? of ethylene oxide on fatty alcohols or on fatty acids or on fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of esters of sulphosuccinic acids, derivatives of taurine (in particular alkyltaurates), phosphoric esters of alcohols or polyoxyethylated phenols, esters of fatty acids and polyols, derivatives with the function of sulphates, sulfonates and phosphates of the preceding compounds. The presence of at least one surfactant agent in general ,? indispensable in the event that the raw material and / or the inert support are not soluble in water and in the event that the substance-vehicle of application is water,
per la loro applicazione, i composti di formula (l) si trovano dunque in generale, sottoforma di composizioni; queste composizioni secondo la presente sono for their application, the compounds of formula (I) are therefore generally found in the form of compositions; these compositions according to the present are
invenzione,/anch'esse, sotto forme molto diverse, solide oppure liquide, invention, / also, in very different forms, solid or liquid,
Come forme di composizioni solide, si possono citare polveri per polverizzazione (aventi un contenuto in un composto di formula (i) che pu? arrivare fino a 100%) e granuli, in particolare quelli ottenuti mediante estrusione, mediante costipamento, mediante impregnazione di un supporto granulato, mediante granulazione partendo da una polvere (il contenuto in composto di formula (l) in questi granuli essendo compreso tra 0,5% e 80% per questi ultimi casi)? As forms of solid compositions, it is possible to mention powders for pulverization (having a content in a compound of formula (i) that can reach up to 100%) and granules, in particular those obtained by extrusion, by compaction, by impregnation of a granulated support, by granulation starting from a powder (the content in compound of formula (1) in these granules being between 0.5% and 80% for the latter cases)?
Le composizioni solide contengono pi? spesso da 20%' The solid compositions contain more? often by 20% '
a 80% di sostanza attiva? to 80% active substance?
Come forme di composizioni liquide oppure As forms of liquid compositions or
destinate a costituire composizioni liquide nel corso dell,ag3Licazionet si possono citare soluzioni, in. particolare concentrati emulsionatali, emulsioni, sospensioni concentrate, aerosol, polveri umidificatali (oppure polvere da polverizzare), grani auto?disperdibili e paste. intended to constitute liquid compositions in the course of bonding, solutions can be mentioned in. particular emulsified concentrates, emulsions, concentrated suspensions, aerosols, humidifying powders (or powder to be pulverized), self-dispersible grains and pastes.
Le composizioni liquide contengono pi? spesso The liquid compositions contain more? often
da 10% a 80 % di sostanza attiva. from 10% to 80% of active substance.
I concentrati emulsionatali oppure solubili contengono pi? spesso dal 10% a 80% di sostanza attiva, le emulsioni oppure le soluzioni pronte per The emulsified or soluble concentrates contain more? often from 10% to 80% of active substance, emulsions or ready-to-use solutions
1*applicazione contenendo, a loro volta, 0,01 fino 1 * application containing, in turn, 0.01 up
a 20% di sostanza attiva. Oltre al solvente, i concentrati emulsionabili possono contenere, quando to 20% of active substance. In addition to the solvent, the emulsifiable concentrates may contain, when
? necessario, da 2% a 20% di additivi opportuni, come stabilizzanti, agenti tensio attivi, agenti di penetrazione, inibitori di corrosione, coloranti. ? necessary, from 2% to 20% of suitable additives, such as stabilizers, surfactant agents, penetrating agents, corrosion inhibitors, dyes.
adesivi stickers
partendo da questi concentrati, si possono ottenere mediante diluizione con acqua emulsioni oppure soluzioni aventi qualsiasi concentrazione desiderata, che sono particolarmente convenienti per l'applicazione sui vegetali,, starting from these concentrates, it is possible to obtain by dilution with water emulsions or solutions having any desired concentration, which are particularly suitable for application on vegetables.
A titolo esemplificativo si riporta la composizione di alcuni concentrati emulsionabili: By way of example, the composition of some emulsifiable concentrates is shown:
? sostanza attiva 250 g ? active substance 250 g
? alchilfenolopolietossilato 30 g ? alkylphenolopolyethoxylate 30 g
? alchilarilsolfonato di calcio 50 g ? calcium alkylaryl sulphonate 50 g
? frazione di distillazione del petrolio, ? oil distillation fraction,
che distilla tra 160?C e 185?C 670 g Altra formula: distilling between 160? C and 185? C 670 g Other formula:
? sostanza attiva 350 g ? active substance 350 g
? olio di ricino polietossilato 60 g ? polyethoxylated castor oil 60 g
- alchilarilsolfonato di sodio 40 g - sodium alkylaryl sulphonate 40 g
? cicloesanone 150 g ? cyclohexanone 150 g
? xilene 400 g Altra formula: ? xylene 400 g Other formula:
? sostanza attiva 400 g ??alchilfenolo polietossilato 100 g ? active substance 400 g ?? alkylphenol polyethoxylate 100 g
? etere metilico del glicol etilenico 250 g ? methyl ether of ethylene glycol 250 g
? frazione del petrolio aromatica che ? fraction of the aromatic oil which
distilla tra 160?185?C 250 g Altra formula distils between 160? 185? C 250 g Other formula
? sostanza attivi 400 g ? active substances 400 g
? fosfato di tristirilfenolo polietossilato 50 g. ? polyethoxylated tristyrylphenol phosphate 50 g.
?^fosfato di alchilfenolo polietossilato 65 g ? ^ polyethoxylated alkylphenol phosphate 65 g
? alchil benzen solfonato di sodio 35 g ? sodium alkyl benzene sulfonate 35 g
? cicloesanone 300 g ? cyclohexanone 300 g
? frazi?ne di petrolio aromatica ? fractions of aromatic petroleum
che distilla tra 160-185?C .150 g Altra formula: distilling between 160-185? C. 150 g Other formula:
? sostanza attiva 400 g/litro ? dodecilbeiEen solfonato alcalino 24 g/litro ? nonilfenolo ossietilato cpn 10 molecole ? active substance 400 g / liter? dodecylbeiEen alkaline sulfonate 24 g / liter? nonylphenol oxyethylated cpn 10 molecules
di ossido di etilene 16 g/litro ? cicloesan?ne 200 g/litro ? solvente aromatico quanto basta a 1 litro. Secondo un?altra forma di concentrato emulsionabile, si impiegano: of ethylene oxide 16 g / liter? cyclohexane? ne 200 g / liter? aromatic solvent as required for 1 liter. According to another form of emulsifiable concentrate, the following are used:
? sostanza attiva 250 g ? olio vegetale epossidato 25 g ? active substance 250 g? epoxidized vegetable oil 25 g
? miscela di solfonato di alchilarile e ? mixture of alkylaryl sulfonate e
di etere di poliglicol e di alcodi.grassi 100 g of polyglycol ether and of alkodes. fats 100 g
- dimetilformammide 50 g - dimethylformamide 50 g
- xilene 575 g - xylene 575 g
Le sospensioni concentrate, che sono applicabili mediante polverizzazione, vengono preparate Concentrated suspensions, which are applicable by spraying, are prepared
in modo da ottenere un prodotto fluido stabile che non si deposita (polverizzazione fine) e contengono usualmente da 10% al 75% di sostanza attiva, da o,5% a 15% di agenti tensio-attivi, da 0,1% a 10% di agenti tissotropici, da 0% a 10% di additivi opportuni, come anti?schiuma, inibitori di corrosione, stabilizzanti, agenti di penetrazione e adesivi e, come supporto, acqua oppure un liquido organico nel quale la so?tanza attiva ? poco solubile oppure ? insolubile: certe sostanze solide organiche oppure sali minerali possono venire sciolti nel supporto per aiutare a impedire la sedimentazione oppure come prodotti antigelo per l'acqua* in order to obtain a stable fluid product that does not settle (fine pulverization) and usually contain from 10% to 75% of active substance, from 0.5% to 15% of surfactant agents, from 0.1% to 10 % of thixotropic agents, from 0% to 10% of suitable additives, such as anti-foam, corrosion inhibitors, stabilizers, penetrating agents and adhesives and, as support, water or an organic liquid in which the active substance? slightly soluble or? insoluble: certain solid organic substances or mineral salts can be dissolved in the support to help prevent sedimentation or as antifreeze products for water *
A titolo esemplificativo, viene riportata qui di seguito una composizione di sospensione concentrata: By way of example, a concentrated suspension composition is reported below:
? sostanza attiva . 50 g ? fosfato di tristirilfenolo polietossilato 50 g ? alchilfenolo polietossilato 50 g ? policarbossilato di sodio ? 20 g ? glicoletilenico 50 g ? olio organopolisilossanico (antischiuma) 1 g ? polisaccaride 12,5 g ? acqua 316,5 g Le polveri umidificabili (o polvere da polverizzare) vengono preparate usualmente in modo che esse contengono 20-95% di sostanza attiva, e esse contengono usualmente, oltre alla sostanza solida di supporto, da 0 a '5% di un agente umidificante, 3-10% di un agente disperdente e quando ? necessario, 0?10% di uno o pi? stabilizzanti e/o altri additivi, come.agenti di penetrazione, adesivi, oppure agenti antiagglomeranti, coloranti, eccee.* ? active substance. 50 g polyethoxylated tristyrylphenol phosphate 50 g? polyethoxylated alkylphenol 50 g? sodium polycarboxylate? 20 g ethylene glycol 50 g? organopolysiloxane oil (antifoam) 1 g? polysaccharide 12.5 g? water 316.5 g The humidifiable powders (or powder to be pulverized) are usually prepared in such a way that they contain 20-95% of active substance, and they usually contain, in addition to the supporting solid substance, from 0 to 5% of a wetting agent, 3-10% of a dispersing agent and when? necessary, 0? 10% of one or more? stabilizers and / or other additives, such as penetrating agents, adhesives, or anti-caking agents, dyes, etc. *
A titolo esemplificativo, vengono riportate qui. , di seguito diverse composizioni di polveri umidifi? cabili: By way of example, they are listed here. , hereinafter various compositions of wet powders? cabili:
? sostanza attiva 50 % ? active substance 50%
? ligninsolfonato di c?lcio (deflocculante) 5 % ? calcium lignosulfonate (deflocculant) 5%
? isopropilnaftalin solfonato (agente tensioattivo anionico) 1 % ? isopropylnaphtalin sulfonate (anionic surfactant) 1%
? silice antiagglomerante 5,% ? anti-caking silica 5,%
? caolino (carica) 39 % ? kaolin (filler) 39%
Qui di seguito viene riportato un altro esempio Here is another example
di polvere umidificabile al'80% : 80% humidifiable powder:
? sostanza attiva 80%r ? active substance 80% r
? alchilnaftalinsolfonato di sodio 2% ? 2% sodium alkylnaphthalinsulphonate
? ligninsolfonato di sodio - 2% ? sodium lignosulfonate - 2%
? silice antiagglomerante 3% ? 3% anti-caking silica
? caolino - 13% ? kaolin - 13%
Qui di seguito viene riportato un altro esempio di polvere umidificabile; Here is another example of a humidifiable powder;
? sostanza attiva 50 % ? alchilnaftalin solfonato di sodio 2i% ? metil cellulosa di bassa viscosit? 2 % ? terra di diatomee 46 % ? active substance 50%? 2% alkylnaphtalin sodium sulfonate? low viscosity methyl cellulose 2 % ? diatomaceous earth 46%
Un altro esempio di polvere umidificabile Another example of a humidifiable powder
viene indicato qui di seguito: is indicated below:
? sostanza attiva 90 % ? diottilsolfosuccinato di sodio 0,2 % ? silice sintetica 9,8 % In un?altra composizione di polvere da polverizzare al 40% si impiegano i seguenti costituenti: ? active substance 90%? 0.2% sodium dioctyl sulfosuccinate? synthetic silica 9.8% In another 40% powder composition to be pulverized, the following constituents are used:
? sostanza attiva 400 g ? ligninsolfonato di sodio 50 g ? dibutilnaftalinsolfonato di sodio 10 g ? silice 540 g In un'altra composizione di polvere da polverizzare al 25% si impiegano i seguenti costituenti: ? sostanza attiva 250 g ? isoottilfenossi-poliossietilene-etanolo 25 g ? miscela equiponderaie di gesso di ? active substance 400 g? sodium lignosulfonate 50 g? sodium dibutylnaphthalin sulfonate 10 g? silica 540 g In another composition of powder to be pulverized at 25% the following constituents are used:? active substance 250 g? isooctylphenoxy-polyoxyethylene-ethanol 25 g? gypsum equipment mixture of
Champagne e di idrossietilcellulosa 17 g ? alluminosilicato di sodio 543 g ? ferina fossile 165 g In un?altra composizione di polvere da polverizzare al 10% si impiegano i seguenti costituenti: Champagne and hydroxyethylcellulose 17 g? sodium aluminosilicate 543 g? fossil ferine 165 g In another 10% powder composition to be pulverized, the following constituents are used:
- sostanza attiva 100 g - miscela di sali di sodio di solfati di acidi grassi saturi 30 g - prodotto di condensazione di acido naftalin solfonico e di formaldeide 50 g - caolino 820 g Per ott?nere queste polveri da polverizzare o polveri umidificabili, si mescolano intimamente le sostanze attive in mescolatori appropriati con le sostanze additive oppure si impregna la sostanza attiva fusa sulla carica porosa e si effettua la macinazione con mulini oppure con altri apparecchi di macinazione opportuni. Si ottengono cosi polveri da polverizzare la cui umidificabilit? e la cui disperdibilit? sono vantaggine ; si possono mettere dette polveri in sospensioni con acqua in corrispondenza di qualsiasi concentrazione desiderata e questa sospensione ? utilizzabile molto vantaggiosamente 9 in particolare per l?applicazione su foglie di vegetali. - active substance 100 g - mixture of sodium salts of sulphates of saturated fatty acids 30 g - condensation product of naphthalene sulphonic acid and formaldehyde 50 g - kaolin 820 g To obtain these powders to be pulverized or humidifiable powders, they are mixed the active substances are intimately mixed in suitable mixers with the additives or the melted active substance is impregnated on the porous filler and the grinding is carried out with mills or with other suitable grinding devices. In this way we obtain powders to pulverize whose humidifiability? and whose dispersibility? they are advantage; can said powders be put in suspensions with water at any desired concentration and this suspension? it can be used very advantageously 9 in particular for application on vegetable leaves.
I granuli "autodisperdibili" ( in lingua inglese "dry flowable"; si tratta pi? esattamente di granuli facilmente disperdibili in acqua ) hanno una composizione sensibilmente prossima a quelle delle polveri umidificabili* Essi possono venire preparati mediante granulazione di formulazioni descritte per le polveri umidificabili, sia per via umida (messa a contatto della sostanza attiva finemente suddivisa con la carica inerte e con un p? di acqua? per esempio 1?20%, oppure con una soluzione acquosa di disperdente o di agente legante, quindi essicamento e setacciatura), sia per via secca ( compattazione,'quindi macinazione e setacciatura ). The "self-dispersible" granules (in English "dry flowable"; more precisely, they are granules that are easily dispersible in water) have a composition sensitively close to that of the humidifiable powders * They can be prepared by granulating the formulations described for the humidifiable powders. , either by wet way (contact of the finely divided active substance with the inert filler and with some water? for example 1? 20%, or with an aqueous solution of dispersant or binding agent, then drying and sieving) , both dry (compaction, then grinding and sieving).
A titolo esemplificativo viene riportata qui di seguito una formulazione di g?nulato autodisperdibile: By way of example, a formulation of self-dispersible g? Nulate is given below:
- sostanza attiva 800 g - alchilnaftalin solfonato di sodio 20 g - metilen bis naftalin solfonato di sodio 80 g - caolino 100 g Al posto delle polveri umidificabili, si possono realizzare paste* Le condizioni e le modalit? di realizzazione e di impiego di queste paste sono para^? gonabili a quelle di polveri umidificabili o polveri da polverizzare* - active substance 800 g - alkylnaphtalin sodium sulfonate 20 g - methylene bis naphthalene sodium sulfonate 80 g - kaolin 100 g of realization and use of these pastes are para. to those of humidifiable powders or powders to be pulverized *
Come ? gi? stato indicato, le dispersioni e le emulsioni acquose, per esempio _ composizioni ottenute diluendo con acqua una polvere umidificabile oppure un concentrato emulsionabile secondo la presente invenzione, sono comprese nell'ambito generale, delle composizioni impiegabili nella presente invenzione. Le emulsioni possono essere del tipo acqua? in-olio oppure olio?in-acqua e possono avere la consistenza densa come quella di una "mayonnaise". How ? already? It has been indicated that the aqueous dispersions and emulsions, for example compositions obtained by diluting a humidifiable powder or an emulsifiable concentrate according to the present invention with water, are included in the general scope of the compositions usable in the present invention. Can the emulsions be of the water type? in-oil or oil? in-water and can have a thick consistency like that of a "mayonnaise".
Tutte queste dispersioni o emulsioni acquose o poltiglie sono applicabili a colture che devono venire disinfestate da erbe infestanti adottando qualsiasi mezzo adatto, principalmente mediante polverizzazione, in corrispondenza di dosi, che in generale, sono dell'ordine di grandezza di 100-1200 litri di poltiglie per ettaro. All these aqueous dispersions or emulsions or slurries are applicable to crops that must be disinfected from weeds by adopting any suitable means, mainly by spraying, in correspondence with doses, which in general, are of the order of magnitude of 100-1200 liters of slurry. per hectare.
I granuli destinati a venire collocati sul terreno vengono preparati usualmente in modo che essi abbiano dimensioni comprese tra 0,1 mm e 2 mm e . ..essi possono venire preparati mediante agglomerazione oppure mediante impregnazione. Preferibilmente, i granuli contengono 1-25% di sostanza attiva e o a 10% di additivi come stabilizzanti, agenti modificanti a rilascio ritardato, agenti leganti e solventi. The granules intended to be placed on the ground are usually prepared so that they have dimensions between 0.1 mm and 2 mm e. .. they can be prepared by agglomeration or by impregnation. Preferably, the granules contain 1-25% active substance and or 10% additives such as stabilizers, delayed release modifying agents, binding agents and solvents.
Secondo un esempio di composizione di granulato, si impiegano i seguenti costituenti: According to an example of granulate composition, the following constituents are used:
? sostanza attiva 50 g glicol propilenico 25 g - argilla (granulometria: 0,3 - 0, 8 mm) 925 g . Come indicato sopra, la presente invenzi?ne riguarda anche un procedimento di diserbo di colture, in particolare cereali come frumento e anche soia, secondo il quale si applica sulle piante e/o sul terreno della zona da diserbare, una quantit? efficace e non fitotossica nei confronti della coltura in questione di almeno uno dei composti secondo la presente invenzione. Questi vengono impiegati praticamente sotto forma di composizioni erbicide secondo la presente invenzione che sono state descritte sopra, in generale, quantit? di sostanza attiva comprese tra 0,01 kg/ettaro e 5 Kg/ettaro, preferibilmente comprese tra 0,1 Kg/ettaro e 2 kg/ettaro, danno buoni risultati, essendo inteso che la scelta della quantit? di sostanza attiva da impiegare ? funzione della gravit? del problema da risolvere, delle condizioni climatiche e della coltura desiderata. Il trattamento pu? venire effettuato sia in pre?emergenza delle colture e delle piante avventizie, oppure in pre?semina delle colture con incorporazione nel'terreno (questa incorporazione ? dunque un'operazione complementare del procedimento di trattamento della presente invenzione), sia in post-emergenza. Si possono adottare inoltre altri metodi di realizzazione del procedimento di trattamento secondo la presente invenzione cos? , si pu? applicare la sostanza atttiva sul terreno, con oppure senza incorporazione, prima del trapianto di una coltura* ? active substance 50 g propylene glycol 25 g - clay (grain size: 0.3 - 0.8 mm) 925 g. As indicated above, the present invention also relates to a process of weeding crops, in particular cereals such as wheat and even soybeans, according to which a quantity of crops is applied to the plants and / or the soil of the area to be weeded. effective and non-phytotoxic towards the crop in question of at least one of the compounds according to the present invention. These are used practically in the form of herbicidal compositions according to the present invention which have been described above in general quantities. of active substance between 0.01 kg / hectare and 5 kg / hectare, preferably between 0.1 kg / hectare and 2 kg / hectare, give good results, it being understood that the choice of quantity? of active substance to be used? function of gravity? the problem to be solved, the climatic conditions and the desired crop. The treatment can? be carried out both in pre-emergence of the crops and adventitious plants, or in pre-sowing of crops with incorporation into the soil (this incorporation is therefore a complementary operation of the treatment process of the present invention), and in post-emergence. It is also possible to adopt other methods of carrying out the treatment process according to the present invention so? , can you? apply the active substance on the soil, with or without incorporation, before transplanting a crop *
Il procedimento di trattamento della presente invenzione viene applicato sia nel caso di colture annuali, che nel caso di colture perenni; in questo caso, si preferisce applicare le sostanze attive della presente invenzione in modo localizzato, per esempio tra le file di dette colture* The treatment process of the present invention is applied both in the case of annual crops and in the case of perennial crops; in this case, it is preferred to apply the active substances of the present invention in a localized way, for example between the rows of said crops *
Col With the
Er inf Er inf
Claims (16)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28699881A | 1981-07-27 | 1981-07-27 | |
US06/286,935 US4744818A (en) | 1981-07-27 | 1981-07-27 | Herbicidal N-halo-5(substituted-phenoxy or -pyridyloxy)-2-substituted benzoic acid sulfonamides and sulfamates |
Publications (3)
Publication Number | Publication Date |
---|---|
IT8222549A0 IT8222549A0 (en) | 1982-07-23 |
IT8222549A1 true IT8222549A1 (en) | 1984-01-23 |
IT1198401B IT1198401B (en) | 1988-12-21 |
Family
ID=26964152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IT22549/82A IT1198401B (en) | 1981-07-27 | 1982-07-23 | HERBICIDAL COMPOUNDS DERIVED FROM PHENOXYBENZOIC ACIDS |
Country Status (21)
Country | Link |
---|---|
KR (1) | KR840000480A (en) |
AU (1) | AU8642882A (en) |
BR (1) | BR8204350A (en) |
DD (1) | DD203679A5 (en) |
DE (1) | DE3227818A1 (en) |
DK (1) | DK333382A (en) |
ES (1) | ES8305715A1 (en) |
FR (1) | FR2510103A1 (en) |
GB (1) | GB2103609A (en) |
GR (1) | GR76231B (en) |
IL (1) | IL66241A0 (en) |
IT (1) | IT1198401B (en) |
LU (1) | LU84296A1 (en) |
MA (1) | MA19550A1 (en) |
NL (1) | NL8202993A (en) |
OA (1) | OA07161A (en) |
PL (1) | PL132197B1 (en) |
PT (1) | PT75320B (en) |
SE (1) | SE8204457L (en) |
SU (1) | SU1149857A3 (en) |
TR (1) | TR21427A (en) |
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TW201101999A (en) * | 2009-06-12 | 2011-01-16 | United Phosphorus Ltd | Herbicidal composition |
Family Cites Families (1)
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EP0003416B1 (en) * | 1978-01-19 | 1981-08-26 | Imperial Chemical Industries Plc | Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them |
-
1982
- 1982-06-25 FR FR8211330A patent/FR2510103A1/en active Granted
- 1982-07-06 IL IL66241A patent/IL66241A0/en unknown
- 1982-07-21 MA MA19758A patent/MA19550A1/en unknown
- 1982-07-23 IT IT22549/82A patent/IT1198401B/en active
- 1982-07-23 PL PL1982237636A patent/PL132197B1/en unknown
- 1982-07-26 LU LU84296A patent/LU84296A1/en unknown
- 1982-07-26 AU AU86428/82A patent/AU8642882A/en not_active Abandoned
- 1982-07-26 GR GR68860A patent/GR76231B/el unknown
- 1982-07-26 DK DK333382A patent/DK333382A/en not_active Application Discontinuation
- 1982-07-26 OA OA57753A patent/OA07161A/en unknown
- 1982-07-26 PT PT75320A patent/PT75320B/en unknown
- 1982-07-26 ES ES514355A patent/ES8305715A1/en not_active Expired
- 1982-07-26 GB GB08221570A patent/GB2103609A/en not_active Withdrawn
- 1982-07-26 DE DE19823227818 patent/DE3227818A1/en not_active Withdrawn
- 1982-07-26 SU SU823467050A patent/SU1149857A3/en active
- 1982-07-26 NL NL8202993A patent/NL8202993A/en not_active Application Discontinuation
- 1982-07-26 SE SE8204457A patent/SE8204457L/en not_active Application Discontinuation
- 1982-07-26 BR BR8204350A patent/BR8204350A/en unknown
- 1982-07-27 TR TR21427A patent/TR21427A/en unknown
- 1982-07-27 DD DD82241977A patent/DD203679A5/en unknown
- 1982-07-27 KR KR1019820003346A patent/KR840000480A/en unknown
Also Published As
Publication number | Publication date |
---|---|
ES514355A0 (en) | 1983-04-16 |
PL237636A1 (en) | 1983-09-12 |
PL132197B1 (en) | 1985-02-28 |
DE3227818A1 (en) | 1983-02-24 |
DD203679A5 (en) | 1983-11-02 |
NL8202993A (en) | 1983-02-16 |
LU84296A1 (en) | 1984-03-22 |
MA19550A1 (en) | 1983-04-01 |
GR76231B (en) | 1984-08-04 |
IT8222549A0 (en) | 1982-07-23 |
IT1198401B (en) | 1988-12-21 |
FR2510103B1 (en) | 1984-06-29 |
BR8204350A (en) | 1983-07-19 |
PT75320A (en) | 1982-08-01 |
PT75320B (en) | 1985-11-29 |
FR2510103A1 (en) | 1983-01-28 |
ES8305715A1 (en) | 1983-04-16 |
DK333382A (en) | 1983-01-28 |
GB2103609A (en) | 1983-02-23 |
KR840000480A (en) | 1984-02-22 |
IL66241A0 (en) | 1982-11-30 |
SU1149857A3 (en) | 1985-04-07 |
SE8204457L (en) | 1983-01-28 |
AU8642882A (en) | 1983-02-03 |
SE8204457D0 (en) | 1982-07-26 |
TR21427A (en) | 1984-06-01 |
OA07161A (en) | 1984-03-31 |
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