DD284583A5 - HERBICIDES AND METHOD FOR PRODUCING THE ACTIVE SUBSTANCES - Google Patents
HERBICIDES AND METHOD FOR PRODUCING THE ACTIVE SUBSTANCES Download PDFInfo
- Publication number
- DD284583A5 DD284583A5 DD89332837A DD33283789A DD284583A5 DD 284583 A5 DD284583 A5 DD 284583A5 DD 89332837 A DD89332837 A DD 89332837A DD 33283789 A DD33283789 A DD 33283789A DD 284583 A5 DD284583 A5 DD 284583A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- pyo
- polyoxethylene
- herbicidal
- hydrogen
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000004009 herbicide Substances 0.000 title abstract description 18
- 239000013543 active substance Substances 0.000 title abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 41
- 239000002253 acid Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000007513 acids Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 5
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract description 4
- 229920000768 polyamine Polymers 0.000 claims abstract description 4
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002193 fatty amides Chemical class 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 150000002462 imidazolines Chemical class 0.000 claims abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- -1 Polyoxypropylene Polymers 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 20
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
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- 239000000080 wetting agent Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims description 6
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 claims description 6
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 claims description 5
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- 239000002794 2,4-DB Substances 0.000 claims description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 3
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- UTDPHALOLFEIHB-UHFFFAOYSA-N 2-dimethylphosphoryl-2-hydroxyacetic acid Chemical compound CP(C)(=O)C(O)C(O)=O UTDPHALOLFEIHB-UHFFFAOYSA-N 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 abstract description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
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- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 5
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/14—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
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- Molecular Biology (AREA)
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- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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- Peptides Or Proteins (AREA)
Abstract
Die Erfindung betrifft herbizide Mittel und Verfahren zur Herstellung der Wirkstoffe durch Umsetzung der als Saeurekomponente zu verwendenden Herbizid-Saeure mit der Basenkomponente in waeszrigem Medium. Die in den erfindungsgemaeszen Mitteln enthaltenen Wirkstoffe sind Salze, welche als Saeurekomponenten Herbizid-Saeuren aus der Gruppe substituierte Phenoxycarbonsaeuren, Phosphinsaeuren der Formel I, worin Y1 H und Y2 Amino oder Y1 und Y2 zusammen ein Sauerstoffatom bedeuten und W Hydroxy oder ein von natuerlichen Aminosaeuren abgeleiteter Mono- oder Dipeptidrest ist, und einer Phosphinylcarbonsaeure der Formel II und als Basenkomponente ein primaeres Fettamin oder Fettamid, ein sekundaeres oder tertiaeres Amin, ein Polyamin, ein alkyliertes, gegebenenfalls oxalkyliertes Imidazolin-Derivat, ein Zuckeramin, ein ggf. oxalkyliertes Aminoethylethanolamin, ein ggf. oxalkyliertes Alkanolamin, ein alkylsubstituiertes, ggf. oxalkyliertes * 1,3- oder 1,4-Diazacyclohexan, Piperidin, Morpholin oder Aminoxid enthalten. Formeln I, II{Mittel herbizid; Salze neu; Phenoxycarbonsaeuren; Phosphinsaeuren; Phosphinylcarbonsaeure; Basenkomponenten}The invention relates to herbicidal compositions and processes for the preparation of the active compounds by reacting the herbicidal acid to be used as the acid component with the base component in a watery medium. The active substances contained in the compositions according to the invention are salts which are acidic components of herbicidal acids from the group consisting of phenoxycarboxylic acids, phosphinic acids of the formula I in which Y.sup.1 H and Y.sup.2 are amino or Y.sup.1 and Y.sup.2 together denote an oxygen atom and W is hydroxy or a derivative derived from natural amino acids Mono- or Dipeptidrest is, and a Phosphinylcarbonsaeure of formula II and as the base component a primary fatty amine or fatty amide, a secondary or tertiary amine, a polyamine, an alkylated, optionally alkoxylated imidazoline derivative, a sugar amine, an optionally alkoxylated aminoethylethanolamine, a possibly alkoxylated alkanolamine, an alkyl-substituted, optionally alkoxylated * 1,3- or 1,4-diazacyclohexane, piperidine, morpholine or amine oxide. Formulas I, II {herbicidal agent; New salts; phenoxycarbon acids; phosphinic; Phosphinylcarbonsaeure; Base component}
Description
Die vonliegende Erfindung betrifft herbizide Mittel, die neue Salze von bestimmten Herbizid-Wirkstoffen, deren Säurekomponente die wirksame Komponente darstellt, enthalten. Solche Salze leiten sich ab von den Wirkstoffsäuren Glufosinate oder von anderen phosphorhaltigen Säuren oder den substituierten Phenoxycarbonsäuren wie MCPA, CMPP oder 2,4-D.The present invention relates to herbicidal compositions containing novel salts of certain herbicidal active ingredients whose acid component is the effective component. Such salts are derived from the active ingredients glufosinate or other phosphorus-containing acids or the substituted phenoxycarboxylic such as MCPA, CMPP or 2,4-D.
Derartige herbizide Wirkstoffe und einige ihrer Salze sind in "The Pesticide Manual", 8. Aufl. (1987), British Crop Protection Council beschrieben. Phosphinsäuren und bestimmte Salze sind auch aus US-PS 4 168 936; US-PS 4 309 208; DE-OS 35 44 375, D. of Antibiotics Vol. 36(1) S. 96-98 (1983) und Vol. 37(2) S. 542 (1985) bekannt. Phosphinylcarbonsäuren und einige ihrer Salze sind xn EP-A 0 106 114 bzw. US-PS 4 594 beschrieben.Such herbicidal agents and some of their salts are described in "The Pesticide Manual", 8th Edition (1987), British Crop Protection Council. Phosphinic acids and certain salts are also disclosed in US Pat. Nos. 4,168,936; U.S. Patent 4,309,208; DE-OS 35 44 375, D. of Antibiotics Vol. 36 (1) pp. 96-98 (1983) and Vol. 37 (2) p. 542 (1985). Phosphinylcarboxylic acids and some of their salts are described in EP-A 0 106 114 and US Pat. No. 4,594, respectively.
Durch die Erfindung werden herbizide Mittel mit deutlich überlegener herbizider Wirkung bereitgestellt.The invention provides herbicidal compositions having markedly superior herbicidal activity.
Der vorliegenden Erfindung liegt die Aufgabe zugrunde, wirk-The present invention is based on the object of
33-064582733-0645827
2 8 4 -Ia-2 8 4 -Ia
samere Herbizids aufzufinden und Verfahren zu deren Herstellung sowie herbizide Mittel bereitzustellen.seedy herbicides and to provide processes for their preparation and herbicidal agents.
Bei der Suche nach Salzen mit überlegenen Anwendungseigenschaften wurde gefunden, daß Salze der genannten Herbizid-Wirkstoffe mit bestimmten langkettigen organischen Stickstoffbasen eine besonders intensive Herbizidwirkung entfalten, die gegenüber den bekannten Salzen deutlich erhöht ist.In the search for salts with superior application properties, it has been found that salts of said herbicidal active compounds with certain long-chain organic nitrogen bases exhibit a particularly intensive herbicidal action, which is markedly increased compared to the known salts.
Gegenstand der Erfindung sind daher herbizide Mittel, die neue Salze von bekannten Herbiziden aus der Gruppe, bestehend aus substituierten Phenoxycarbonsäuren, Phosphinsäuren der FormelThe invention therefore provides herbicidal agents, the novel salts of known herbicides from the group consisting of substituted phenoxycarboxylic acids, phosphinic acids of the formula
Y1 Y 1
I IlI Il
- CH2CH2 - ι- CH 2 CH 2 - ι
OH YOH Y
H3C - P - CH2CH2 - C - C - V/H 3 C - P - CH 2 CH 2 - C - C - V /
enthalten, worincontain, in which
22
Y '/Wasserstoff und Y Amino oder Y und Y zusammen einY '/ hydrogen and Y amino or Y and Y together
Sauerstoffatom bedeuten und VV Hydroxy oder ein von natürlichen AminosäurenOxygen atom and VV hydroxy or one of natural amino acids
abgeleiteter Mono- oder Dipeptidrast ist, und einsr Phosphinylcarbonsäurs der Formel 0derived mono or dipeptide residue, and one phosphinylcarboxylic acid of formula 0
IlIl
H3C - P - CH - COOHH 3 C - P - CH - COOH
CH-, OHCH-, OH
dadurch gekennzeichnet, daß sie als Basenkomponente enthalten:characterized in that they contain as base component:
a) ein primäres Fettamin oder Fettamid der Formeln (Ia) oder (Ib)a) a primary fatty amine or fatty amide of the formulas (Ia) or (Ib)
R1 — NX, R1 — erR 1 - NX, R 1 - he
(Ia) (Ib)(Ia) (Ib)
worinwherein
R1= ein gesättigter oder ein- oder mehrfachR 1 = a saturated one or more times
ungesättigter Rest mit 6-22 C-Atomen, bevorzugt 12 - 14 oder 16 - 18 C-Atomen; 15unsaturated radical having 6-22 C atoms, preferably 12-14 or 16-18 C atoms; 15
Alkyl- oder Alkenylphenyi, Alkyl- oder Alkenylcyclohexyl, wobei der Alkyl- oder AlkenylrestAlkyl or Alkenylphenyi, alkyl or Alkenylcyclohexyl, wherein the alkyl or alkenyl radical
jeweils 1-30 C-Atome, bevorzugt 8-12 C-Atome enthält, und 20each containing 1-30 C atoms, preferably 8-12 C atoms, and 20
X= Wasserstoff, Polyoxethylen mit 1-40 Mol EO,X = hydrogen, polyoxethylene with 1-40 mol EO,
bevorzugt 2-20 Mol EO (EO= Ethylenoxid-Einheit), insbesondere Polyoxethylen mit 2 bis 15 Mol EO, oderpreferably 2-20 moles of EO (EO = ethylene oxide unit), in particular polyoxethylene with 2 to 15 moles of EO, or
25 Polyoxypropylen mit 1-45 Mol PyO, bevorzugt 2-1525 polyoxypropylene with 1-45 moles of PyO, preferably 2-15
Mol PyO (PyO= Propylenoxid-Einheit), oder einMol PyO (PyO = propylene oxide unit), or a
Polyoxypropylen/Polyoxethylen-Blockcopolymerisat im folgenden "Blockpolymerisat A" genannt, mit einemPolyoxypropylene / polyoxyethylene block copolymer in the following called "block polymer A", with a
30 Molverhältnis PyO/EO von 1:9 bis 9:1, bevorzugt "1:1,30 molar ratio PyO / EO of 1: 9 to 9: 1, preferably "1: 1,
2:1 oder 1:2, bedeutet;2: 1 or 1: 2, means;
b) ein sekundäres oder tertiäres Amin der Formeln (Ha), 35 (Hb) oder (lic).b) a secondary or tertiary amine of the formulas (Ha), 35 (Hb) or (lic).
? δ ; 5 ö 3? δ; 5 ö 3
worinwherein
R1 die obengenannte Bedeutung besitzt,R 1 has the abovementioned meaning,
c) ein Polyamin der nachfolgend unter C1) - C^.) definierten 10 Formeln (HIa)7 (HIb), (HIc) ode.r (HId)c) a polyamine of the formula (HIa) 7 (HIb), (HIc) ode.r (HId) defined below under C 1 ) - C ^.)
C1) R2-A-N[(CH2)r-NC]m [(CH2)J.-NX2]n (IHa)C 1 ) R 2 -AN [(CH 2 ) r -NC] m [(CH 2 ) J.-NX 2 ] n (IHa)
worin R- ein gesättigter oder ein- oder mehrfachwherein R- is a saturated one or more times
ungesättigter aliphatischer Rest mit 1-21 C-Atomen, bevorzugt 1 - 3, 11 - 13 oder 15 - 17 C-Atomen,unsaturated aliphatic radical having 1-21 C atoms, preferably 1 to 3, 11 to 13 or 15 to 17 C atoms,
A= -CO- oder -CH2- , insbesondere -CH2- / m = die Zahl 0, 2, 6 oder 14, vorzugsweise 0, 2 oder 6,A = -CO- or -CH 2 -, in particular -CH 2 - / m = the number 0, 2, 6 or 14, preferably 0, 2 or 6,
insbesondere 0, η = m + 2, undin particular 0, η = m + 2, and
r = 2 oder 3, bevorzugt 3, bedeutet, 25r = 2 or 3, preferably 3, means 25
C2) R2-A-NZ1-[ (CH2)^NZ1) ]s-(CH2)r N(Z1J2 (HIb)C 2 ) R 2 -A-NZ 1 - [(CH 2 ) 2 NZ 1 )] s - (CH 2 ) r N (Z 1 J 2 (HIb)
worinwherein
s = eine ganze Zahl von 1-20, vorzugsweise 1 bis 4 Z1= Wasserstoff oder Polyoxethylen mit 4-70 EO,s = an integer of 1-20, preferably 1 to 4 Z 1 = hydrogen or polyoxethylene with 4-70 EO,
bevorzugt 8-20 EO, Polyoxpropylen mit 4-60 PyO, bevorzugt 8-15 PyO oder ein Blockpolymerisat A, bedeutet,preferably 8-20 EO, polyoxpropylene with 4-60 PyO, preferably 8-15 PyO or a block polymer A,
C3) (Z2)2N- [(CH2)p-NZ2]o-(CH2)p-N(Z2)2 (HIc)C 3 ) (Z 2 ) 2 N- [(CH 2 ) p -NZ 2 ] o - (CH 2 ) p -N (Z 2 ) 2 (HIc)
worinwherein
o= eine ganze Zahl von 0 bis 4,o = an integer from 0 to 4,
ρ= unabhängig voneinander eine ganze Zahl von 2 bis 6, bevorzugt 2 - 3,ρ = independently of one another an integer from 2 to 6, preferably 2 to 3,
Z2= Wasserstoff, Polyoxethylen mit 5-70 EO, bevorzugt 5 8-25 EO, Polyoxpropylen mit 4-60 PyO, bevorzugtZ 2 = hydrogen, polyoxethylene with 5-70 EO, preferably 5 8-25 EO, polyoxpropylene with 4-60 PyO, preferred
8-30 PyO oder ein Blockpolymerisat A bedeutet, (hierzu zählt beispielsweise die Verbindung NH2- CH2- CH2- NH- CH2- CH2- NH2 )/ 8-30 pyo or a block polymer A means (this includes, for example, the compound NH 2 - CH 2 - CH 2 - NH- CH 2 - CH 2 - NH 2) /
C4) (Z2 )2N-CH2CH2-N (Z2) 2 (HId)C 4 ) (Z 2 ) 2 N-CH 2 CH 2 -N (Z 2 ) 2 (HId)
worinwherein
Z- unabhängig voneinander Wasserstoff, 2-Hydroxy-prop-1-yl oder 2-Hydroxy-eth-l-yl, vorzugsweise 2-Hydroxypropyl oder 2-Hydroxyethyl bedeutet,, 15Z independently of one another hydrogen, 2-hydroxy-prop-1-yl or 2-hydroxy-eth-1-yl, preferably 2-hydroxypropyl or 2-hydroxyethyl, means
d) ein Imidazolin-Derivat der Formeln (IVa) oder (IVb)d) an imidazoline derivative of the formulas (IVa) or (IVb)
N N-X1 (IVa)N NX 1 (IVa)
ΓΛΓΛ
R3 R 3
worinwherein
R= ein gesättigter oder ein- oder mehrfach ungesättigter 25 aliphatischer Rest mit 7 bis 21 C-Atomen, bevorzugtR = a saturated or mono- or polyunsaturated aliphatic radical having 7 to 21 C atoms, preferably
12 - 14 oder 16 - 18 C-Atomen/ 12 - 14 or 16 - 18 C atoms /
X= Wasserstoff oder -CO-R oder Polyoxethylen mitX = hydrogen or -CO-R or polyoxethylene with
1-55 EO, bevorzugt 4-20 EO, Polyoxpropylen mit 30 1- 40 PyO, bevorzugt 4-12 PyO oder ein1-55 EO, preferably 4-20 EO, polyoxpropylene with 30 1-40 PyO, preferably 4-12 PyO or a
Blockpolymerisat A und R= (C1-C22)AIkYl, bevorzugt (C1-Cg)AIkYl bedeutet,Block polymer A and R = (C 1 -C 22 ) AlKyl, preferably (C 1 -Cg) AlKyl,
ΓΛΓΛ
d2) N N-CH2-CH2-N(X^)2 (IVb),d 2 ) N N-CH 2 -CH 2 -N (X 1) 2 (IVb),
worinwherein
R= ein gesättigter oder ein- oder mehrfach ungesättigter aliphatischer Rest mit 6 bis 22 C-Atomen, bevorzugt 12 - 14 C-Atomen, und 5 X= unabhängig voneinander Wasserstoff, Polyoxethylen mit 2-55, bevorzugt 2-22 EO, Polyoxpropylen mit 1-40, bevorzugt 2-14 PyO, oder ein Blockpolymerisat A bedeutet,R = a saturated or mono- or polyunsaturated aliphatic radical having 6 to 22 C atoms, preferably 12-14 C atoms, and 5 X = independently of one another hydrogen, polyoxethylene with 2-55, preferably 2-22 EO, polyoxpropylene with 1-40, preferably 2-14 PyO, or a block polymer A,
10 e) ein Zuckeramin der Formeln (Va) oder (Vb)E) a sugar amine of the formulas (Va) or (Vb)
OH HHHIH H HOH HHHIH H H
I I I i
HC-C-C-C-C- CH2 H-CHC-CCCC-CH 2 HC
-i--i-
L I H ' I 1 ι L I H 'I 1 ι
OH OH OH NH OF ~OH OH OH NH OF ~
OH OH OH OH NH OH OHOH OH OH OH NH OH
x·3 x · 3
(Va) (Vb)(Va) (Vb)
X·3 X · 3
worinwherein
X3= Wasserstoff, (C1-C25)AIkYl, (C2-C25)Alkenyl oderX 3 = hydrogen, (C 1 -C 25 ) Alkyl, (C 2 -C 25 ) alkenyl or
20 -CH2-CH2-OH, bevorzugt Wasserstoff, CH3, C12H25 oder20 -CH 2 -CH 2 -OH, preferably hydrogen, CH 3 , C 12 H 25 or
CH2-CH2-OH bedeutet,CH 2 -CH 2 -OH,
f) ein Aminoethylethanolamin der Formel (VI) 25f) an aminoethylethanolamine of the formula (VI) 25
(X4J2N-CH2-CH2-NX4-CH2-CH2-OX4 (VI),(X 4 J 2 N-CH 2 -CH 2 -NX 4 -CH 2 -CH 2 -OX 4 (VI)
worinwherein
X= unabhängig voneinander Wasserstoff, Polyoxethylen 30 mit 2 - 55, bevorzugt 4-25 EO, Polyoxpropylen mitX = independently hydrogen, polyoxethylene 30 with 2-55, preferably 4-25 EO, polyoxpropylene with
2-45, bevorzugt 4-35 PyO- oder ein2-45, preferably 4-35 PyO - or a
Blockpolymerisat A bedeutet,Block polymer A means
g) ein Alkanolamin der Formel (VII) 35g) an alkanolamine of the formula (VII) 35
6 2 3 4 5 8 3 6 2 3 4 5 8 3
CH2-CH2-OX6 X5-N^ (VIi;CH 2 -CH 2 -OX 6 X 5 -N ^ (VIi;
CH2-CH2-OX6 worin 5 X5= H, CH3, CH2-CH3, CH2-CH2-CH3, CH2-CH2-OX6 oder dieCH 2 -CH 2 -OX 6 wherein 5 X 5 = H, CH 3 , CH 2 -CH 3 , CH 2 -CH 2 -CH 3 , CH 2 -CH 2 -OX 6 or the
Bedeutung von X6 undMeaning of X 6 and
X6= unabhängig voneinander Wasserstoff, Polyoxethylen mit 2-55 EO, bevorzugt 4- 15 EO, Polyoxpropylen mit 2-40 PyO, bevorzugt 2-12 PyO oder ein 10 Blockpolymerisat AX 6 = independently of one another hydrogen, polyoxethylene with 2-55 EO, preferably 4-15 EO, polyoxpropylene with 2-40 PyO, preferably 2-12 PyO or a 10 block polymer A.
bedeutet,means
h) eine Verbindung der Formeln (Villa), (VIIIb) oder (VIIIc)h) a compound of the formulas (Villa), (VIIIb) or (VIIIc)
15 X7 15 X 7
,6, 6
(Villa) (VIIIb) (VIIIc)(Villa) (VIIIb) (VIIIc)
worinwherein
R= ein gesättigter oder ein- oder mehrfach ungesättigter 25 aliphatisolier Rest mit 1-22 C-Atomen, bevorzugtR = a saturated or mono- or polyunsaturated radical having 1-22 C atoms, preferably
12 - 14 oder 16 - 18 C-Atomen und12 - 14 or 16 - 18 carbon atoms and
X- unabhängig voneinander Wasserstoff, PolyoxethylenX- independently hydrogen, polyoxethylene
mit 2-60 EO, bevorzugt 8-30 EO, Polyoxpropylen 30 mit 2-50 PyO, bevorzugt 4-20 PyO oder einwith 2-60 EO, preferably 8-30 EO, polyoxpropylene 30 with 2-50 PyO, preferably 4-20 PyO or a
Blockpolymerisat A bedeutet,Block polymer A means
i) ein Piperidin-Derivat der Formel (IX) 35 I —\ R6 i) a piperidine derivative of the formula (IX) 35 I - \ R 6
Ν" (IX)Ν "(IX)
X8 X 8
3 4 3 S 33 4 3 S 3
worinwherein
X8= Wasserstoff, Polyoxethylen mit 1- 50 EO, bevorzugt 4-18 EO, Polyoxpropylen 1-40 PyO, bevorzugt 2-12 PyO oder ein Blockpolymerisat A bedeutet,X 8 = hydrogen, polyoxethylene having 1-50 EO, preferably 4-18 EO, polyoxpropylene 1-40 PyO, preferably 2-12 PyO or a block polymer A,
j) ein Morpholin-Derivat der Formel (X)j) a morpholine derivative of the formula (X)
(X)(X)
x: x :
worinwherein
X= Wasserstoff, Polyoxethylen mit 1- 65 EO, bevorzugt 4-25 EO, Polyoxpropylen mit 1-50 PyO, bevorzugt 4-15 PyO oder ein Blockpolymerisat A bedeutet,X = hydrogen, polyoxethylene having 1-65 EO, preferably 4-25 EO, polyoxpropylene having 1-50 PyO, preferably 4-15 PyO or a block polymer A,
oder die Bedeutung von R1 oder R-1^-CO- besitzt, oderor has the meaning of R 1 or R 1 1 -CO-, or
. k) ein Aminoxid der Formel (XI), k) an amine oxide of the formula (XI)
SS
R6-N(X10)2 (XI)R 6 -N (X 10 ) 2 (XI)
worinwherein
χ10= (C1-C5)AIkYl, bevorzugt (C1-C2)AIkYl,= 10 = (C 1 -C 5 ) alkyl, preferably (C 1 -C 2 ) alkyl,
Polyoxethylen mit 1-65 EO, bevorzugt 2-20 EO, Polyoxpropylen mit 1-45 PyO, bevorzugt 2- 15 PyO,Polyoxethylene with 1-65 EO, preferably 2-20 EO, polyoxpropylene with 1-45 PyO, preferably 2-15 PyO,
oder ein Blockpolymerisat A bedeutet.or a block polymer A means.
Bei den Resten R1, R2, R3, R6 ist der aliphatische Rest, falls er ungesättigt ist, vorzugsweise ein- oder zweifach ungesättigt. Bevorzugt sind jedoch gesättigte aliphatische (=Alkyl)Reste.In the case of the radicals R 1 , R 2 , R 3 , R 6 , the aliphatic radical, if it is unsaturated, is preferably mono- or diunsaturated. However, preferred are saturated aliphatic (= alkyl) radicals.
Die Polyamine des Typs C1) sind sternförmig konfiguriert in der Weise, daß für m= >0 die mit m indizierten Amino-Reste (CH2)r-NC untereinander so verknüpft sind, daß der entstehende Rest verzweigt ist und nur an den EndenThe polyamines of type C 1 ) are configured star-shaped in such a way that for m => 0, the m-indexed amino radicals (CH 2 ) r -NC are linked to one another such that the resulting radical is branched and only at the ends
ο /> ο ,; τ ί η ο />ο,; τ ί η
O ζ_ '*J ι' O J \j O ζ_ '* J ι ' OJ \ j
Stickstoffatome mit freien Valenzen auftreten, die durch die Reste -(CH2)r-NX2 substituiert sind. So ist beispielsweise für m = 4 die Konstitution demnach wie folgt:Nitrogen atoms occur with free valences, which are substituted by the radicals - (CH 2 ) r -NX 2 . For example, for m = 4, the constitution is as follows:
^,(CH2 )r{N-(CH2 )r-NX2]2 ^, (CH 2 ) r {N- (CH 2 ) r -NX 2 ] 2
~(CH2)r{N-(CH2)r-NX2]2 R2-A-N~ (CH 2 ) r {N- (CH 2 ) r -NX 2 ] 2 R 2 -AN
\ (CH2)r{N-(CH2)r-NX2]2 \ (CH 2 ) r {N- (CH 2 ) r -NX 2 ] 2
(CH2)r-N^(CH 2 ) r -N ^
ίCH2)r{N-(CH2)r-NX2] 2 ίCH 2 ) r {N- (CH 2 ) r -NX 2 ] 2
Als Beispiele für die Amine des Typs a) (Formel Ia) sind 15 insbesondere zu nennen: Cocosfettamin, Talgfettamin, als Beispiele für Amine des Typs b) (Formel IIa) insbesondere Dioctylamin, Didecylamin, Dimethylcocosfettamin, die alleExamples of amines of type a) (formula Ia) include, in particular: coconut fatty amine, tallow fatty amine, as examples of amines of type b) (formula IIa), in particular dioctylamine, didecylamine, dimethylcocosaminetamine, all
wie oben angegeben ethoxyliert oder propoxyliert,ethoxylated or propoxylated as indicated above,
insbesondere ethoxyliert, sein können. 20especially ethoxylated, may be. 20
Als Säurekomponenten für die genannten Wirkstoffsalze können beispielsweise eingesetzt werden:As acid components for the mentioned active substance salts it is possible to use for example:
a) substituierte Phenoxycarbonsäuren wie (4-Chlor-2-methyl-25 phenoxy)essigsäure (MCPA), 2-(4-Chlor-2-methyl-phenoxy)-a) substituted phenoxycarboxylic acids such as (4-chloro-2-methyl-25-phenoxy) acetic acid (MCPA), 2- (4-chloro-2-methyl-phenoxy) -
propionsäure (Mecoprop), 2,4-Dichlorphenoxyessigsäure# (2,4-D); 2,4,5-Trichlorphenoxyessigsäure (2,4,5-T) oder 4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB) oder 2-[4-(2,4-Dichlor-phenoxy)-phenoxy]-propionsäure 30 (Diclofop) oder 2-[4-(6-Chlorbenzoxazol-2-yloxy)-phenoxy]-propionsäure (Fenoxaprop);propionic acid (mecoprop), 2,4-dichlorophenoxyacetic acid # (2,4-D); 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) or 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB) or 2- [4- (2,4-dichlorophenoxy) - phenoxy] -propionic acid 30 (diclofop) or 2- [4- (6-chlorobenzoxazol-2-yloxy) -phenoxy] -propionic acid (fenoxaprop);
b) Phosphinsäuren der Formel (XII)b) Phosphinic acids of the formula (XII)
0 Y1 00 Y 1 0
Il I IlIl I Il
H3C - P - CH2 - CH2 - C - C - W (XU)H 3 C - P - CH 2 - CH 2 - C - C - W (XU)
OH γ2 OH γ 2
2 8 4 5 3 32 8 4 5 3 3
worinwherein
Y1= H,Y 1 = H,
Y2= NH2 oderY 2 = NH 2 or
-ι ο-ι ο
Y und Y zusammen = 0Y and Y together = 0
W= OH oder ein Mono- oder Dipeptidrest abgeleitet von den natürlichen Aminosäuren, bevorzugt die Verbindungen der Formel XII mit Y1= H7 Y2= NH2 und W= OH (XIIa, common name = Glufosinate), -NHCH(CH3)-CONHCH(CH3)-COOH (XIIb, common name= Bialaphos) oder -CH(CH3J-CONH-CH[CH2CH-(CH3J2]COOH (XIIc; common name: Phosalacine),W = OH or a mono- or dipeptide radical derived from the natural amino acids, preferably the compounds of the formula XII where Y 1 = H 7 Y 2 = NH 2 and W = OH (XIIa, common name = glufosinate), -NHCH (CH 3 ) -CONHCH (CH 3 ) -COOH (XIIb, common name = bialaphos) or -CH (CH 3 J-CONH-CH [CH 2 CH- (CH 3 J 2 ] COOH (XIIc; common name: phosalacine),
c) die Phosphinylcarbonsäure der Formel (XIII)c) the phosphinylcarboxylic acid of the formula (XIII)
0 Il0 Il
H3C -P-CH- COOH (XIII)H 3 C -P-CH-COOH (XIII)
CH3 OHCH 3 OH
Die genannten Herbizide und einige ihrer Salze sind zum großen Teil in "The Pesticide Manual", 8. Aufl. (1987), British Crop Protection Council beschrieben. DieThe herbicides mentioned and some of their salts are described in large part in "The Pesticide Manual", 8th Ed. (1987), British Crop Protection Council. The
Verbindungen der Formel XII und bestimmte Salze sind auch aus US-PS 4,168,936; US-PS 4 309 208, DE-OS 35 44 375, J. of Antibiotics Vol. 36(1) S. 96-98 (1983) und Vol. 37(2) S. 542 (1985) bekannt. Die Verbindung der Formel XIII undCompounds of formula XII and certain salts are also disclosed in U.S. Patent 4,168,936; US Pat. No. 4,309,208, DE-OS 35 44 375, J. of Antibiotics Vol. 36 (1) pp. 96-98 (1983) and Vol. 37 (2) p. 542 (1985). The compound of the formula XIII and
einige ihrer Salze ist in EP-A 0106114 bzw. US-PS 4 594 098 beschrieben.Some of their salts are described in EP-A 0106114 and US-PS 4 594 098, respectively.
Die obengenannten Herbizide können soweit sie optisch aktive Zentren enthalten, z.B. die Verbindungen XIIa - XIIb 30 oder Verbindung XIII als Racemate oder in Form ihrerThe above-mentioned herbicides, insofar as they contain optically active centers, e.g. the compounds XIIa - XIIb 30 or compound XIII as racemates or in the form of their
Enantiomeren eingesetzt werden. Von der Erfindung werden daher sowohl die Racematsalze wie auch die Salze der Enantiomeren oder beliebige Mischungen derselben erfaßt.Enantiomers are used. Therefore, both the racemate salts and the salts of the enantiomers or any mixtures thereof are covered by the invention.
Die erfindungsgemäßen Salze besitzen im Vergleich zu den bekannten Salzen wie z.B. dem Ammoniumsalz von Verbindung XIIa oder dem Na-SaIz von Verbindung XIII eine deutlich überlegene herbizide Wirkung.The salts of the invention have compared to the known salts such. the ammonium salt of compound XIIa or the Na salt of compound XIII a significantly superior herbicidal activity.
ίο 2 8 4 5 3 32ο 2 8 4 5 3 3
Zur Herstellung der erfindungsgemäßen Salze werden die Herbizid-Säuren mit den Basenkomponenten in wäßrigem Medium umgesetzt. Beispielsweise werden die Herbizid-Säuren in Wasser gelöst oder dispergiert und vorzugsweise bei Temperaturen zwischen 25 und 500C mit der obengenannten, gegebenenfalls geeignet gelösten Base oder einem Gemisch derselben tropfenweise versetzt.To prepare the salts according to the invention, the herbicidal acids are reacted with the base components in an aqueous medium. For example, the herbicidal acids are dissolved or dispersed in water and preferably added dropwise at temperatures between 25 and 50 0 C with the above, optionally suitably dissolved base or a mixture thereof.
Zweckmäßig geschieht dies durch Zutropfen oder Zulaufen der Base unter Temperaturkontrolle.This is conveniently done by dropwise addition or running the base under temperature control.
Es ist nicht erforderlich, äquimolare Mengen der Reaktionspartner einzusetzen, da die erfindungsgemäßen Salze bei ihrer Anwendung in Mischung mit der Herbizid-15 Säure vorliegen können. Durch Wahl entsprechenderIt is not necessary to use equimolar amounts of the reactants, since the salts according to the invention may be present in their use in admixture with the herbicide acid. By choosing appropriate
Mischungsverhältnisse können sowohl die Ökotoxizität als auch die biologische Wirksamkeit beeinflußt bzw. optimiert werden.Mixing conditions can be influenced or optimized both the ecotoxicity and the biological effectiveness.
Bei schlechter Löslichkeit der Salze in Wasser ist der Einsatz von Lösevermittlern wie (C^-CgJ-Alkanolen, beispielsweise Isopropanol oder Diolen wie Propylenglykol, Ethylenglykol, ferner Polyglykolen oder Dimethylformamid zweckmäßig.In the case of poor solubility of the salts in water, the use of solubilizers such as (C 1 -C 6) -alkanols, for example isopropanol or diols, such as propylene glycol, ethylene glycol, furthermore polyglycols or dimethylformamide, is expedient.
Die vorteilhafte Wirkung der erfindungsgemäßen Salze kann noch durch Zugabe von anionischen oder nichtionischen Netzmitteln oder von Elektrolyten wie beispielsweise Ammoniumchlorid oder Ammoniumsulfat verstärkt werden. Die Netzmittel oder Elektrolyte können entweder in die Lösung bzw. Formulierung der Salze eingearbeitet oder als Tankmix-Zusätze hinzugefügt werden. Ausreichend sind 0,01-0,9 Gew.-% bevorzugt 0,1-0,3 Gew.-% Netzmittel und/oder Elektrolyt bezogen auf die Spritzbrühe.The beneficial effect of the salts according to the invention can be further enhanced by adding anionic or nonionic wetting agents or electrolytes such as ammonium chloride or ammonium sulfate. The wetting agents or electrolytes can either be incorporated into the solution or formulation of the salts or added as tank mix additives. Sufficient are 0.01-0.9 wt .-%, preferably 0.1-0.3 wt .-% wetting agent and / or electrolyte based on the spray mixture.
Als anionische Netzmittel kommen in Frage u.a. Alkali-, Erdalkali- und Ammonium-Salze von Alkyl-aryl-sulfonsäuren mit einem (C6-C30)- bevorzugt (Cg-C12)Alkyl-Rest, vonAs anionic wetting agents are, inter alia, alkali metal, alkaline earth metal and ammonium salts of alkyl-aryl-sulfonic acids having a (C 6 -C 30 ) - preferably (Cg-C 12 ) alkyl radical of
• Ii 2 8 4 5 3 3• Ii 2 8 4 5 3 3
Alkylsulfaten mit einem (C6-C1Q)Alkyl-, bevorzugt (Cg-C14)Alkyl-Rest oder von (C12-ci5JAlkyl)-polyglykolethersulfaten mit 1-10, bevorzugt 2-5 EO, oder Partialester der mit Alkali, Erdalkali oder Ammoniak ganz oder teilweise neutralisierten Orthophosphorsäure^ Die Partialester können gebildet werden z.B. mit Alkylphenolpolyglykolethern mit einem (C6-C3Q), bevorzugt (Cg-C12)Alkyl-Rest und ***** 2-50 EO, bevorzugt 4-10 EO, ferner mit Fettalkoholen, Fettalkoholpolyglykolethern mit einem (Cg-C22) - bevorzugt (C12-C14) -, oder (C16-C18)-Fettalkoholrest, mit 2,4,6-Tri(l-phenylethyl)-phenolpolyglykolethern mit 1-60 EO, bevorzugt 4-30 EO oder mit anderen Verbindungen.Alkyl sulfates having a (C 6 -C 1 Q) alkyl, preferably (Cg-C 14 ) alkyl radical or (C 12 - C i5JAlkyl) polyglycol ether with 1-10, preferably 2-5 EO, or partial esters with Alkali, alkaline earth or ammonia completely or partially neutralized orthophosphoric acid ^ The partial esters can be formed, for example, with alkylphenolpolyglycol ethers having a (C 6 -C 3Q), preferably (C g -C 12 ) alkyl radical and ***** 2-50 EO, preferably 4-10 EO, furthermore with fatty alcohols, fatty alcohol polyglycol ethers having a (Cg-C 22 ) - preferably (C 12 -C 14 ) -, or (C 16 -C 18 ) -fatty alcohol residue, with 2,4,6-tri ( 1-phenylethyl) phenol polyglycol ethers having 1-60 EO, preferably 4-30 EO or with other compounds.
15 Als nichtionische Netzmittel bzw. Additive können15 As non-ionic wetting agents or additives
eingesetzt werden: Alkylphenylpolyglykolether mit einem (C6-C30)-bevorzugt (CQ-C12)-Alkylrest und 2-50 EO, bevorzugt 4 - 10 EO, Fettalkoholpolyglykolether mit einem <C6-C22)' bevorzugt (C12-C14) oder (C16-C18)-Fettalkoholrest mit 1-50, bevorzugt 2-10 EO, sowie Derivate dieser Verbindungen, die einen entständigen Methyl- oder Isocyanatrest enthalten, z.B. veretherte Verbindungen der obengenannten nichtionischen Substanzen.are used: alkylphenyl polyglycol ether with a (C 6 -C 30)-preferably (C Q -C 12) alkyl radical and 2-50 EO, preferably 4 - 10 EO, fatty alcohol polyglycol ethers with a <C 6- C 22) 'preferably (C 12 -C 14 ) or (C 16 -C 18 ) -Fettalkoholrest with 1-50, preferably 2-10 EO, and derivatives of these compounds containing an entstehende methyl or Isocyanatrest, eg etherified compounds of the above-mentioned nonionic substances.
Die Wirkungsverstärkung dieser Netzmittel äußert sich zum Teil überraschenderweise auch in einer Selektivitätssteigerung der betreffenden Salze. So wurde beobachtet, daß monokotyle Pflanzen wie Hordeum vulgäre kaum geschädigt werden, dikotyle Pflanzen wie Sinapis albaThe effect enhancement of these wetting agents is expressed, in part, surprisingly, in an increase in the selectivity of the salts in question. It has been observed that monocotyledonous plants such as Hordeum vulgaris are hardly damaged, dicotyledonous plants such as Sinapis alba
30 oder Chrysanthemum segetum aber vollständig kontrolliert werden.30 or Chrysanthemum segetum but are completely controlled.
Die erfindungsgemäßen Mittel können als Spritzpulver, emulgierbare Konzentrate, versprühbare Lösungen, 35 Stäubemittel, Beizmittel, Dispersionen, Granulate oder Mikrogranulate in den üblichen Zubereitungen angewendet werden; bevorzugt ist der Einsatz von wäßrigen Lösungen.The compositions according to the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, sprays, mordants, dispersions, granules or microgranules in the customary formulations; preferred is the use of aqueous solutions.
; 8 ; 8th
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer gegebenenfalls einem Verdünnungs- oder Inertstoff noch Netzmittel, z.B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenylsulfonate und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,61-disulfonsaures Natrium, dibutylnaphthalinsulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Die Herstellung erfolgt in üblicher Weise, z.B. durch Mahlen und Vermischen der Komponenten.Injectable powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, optionally also a diluent or inert substance, are wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenylsulphonates and dispersants, for example sodium lignosulphonate, 2,2'-dinaphthylmethane-6,6 1- disulfonic acid sodium, dibutylnaphthalenesulfonate sodium or oleoylmethyltaurine acid. The preparation is carried out in a customary manner, for example by grinding and mixing the components.
Emulgierbare Konzentrate können z.B. durch Auflösen des Wirkstoffes in einem inerten organischen Lösungsmittel,Emulsifiable concentrates may e.g. by dissolving the active ingredient in an inert organic solvent,
z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt werden. Bei flüssigen Wirkstoffen kann der Lösungsmittelanteil auch ganz oder teilweise entfallen. Alse.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the solvent content may also be omitted in whole or in part. When
20 Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calciumsalze wieFor example, emulsifiers may be used: alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkyl-arylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Fettalkohol-Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyglykolether, Sorbitanfettsäureester, Polyoxethylensorbitanfettsäureester oder Polyoxethylensorbitester.Calcium dodecyl benzene sulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide-ethylene oxide condensation products, alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
Stäubemittel kann man durch Vermählen des Wirkstoffes mit feinverteilten, festen Stoffen z.B. Talkum, natürlichen Tonen wie Kaolin, Bentonit, Pyrophillit oder Diatomeenerde erhalten.Dusts may be obtained by grinding the active ingredient with finely divided solid materials, e.g. Talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth obtained.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen vonGranules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentrationen mittels Bindemitteln, z.B. Polyvinylalkohol, polyacrylsaurjem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können 5 geeignete Wirkstoffe in der für die Herstellung vonDrug concentrations by binders, e.g. Polyvinyl alcohol, polyacrylsaurjem sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable for the production of 5 suitable active ingredients
Düngemittelgranulaten üblichen Weise, gewünschtenfalls in Mischung mit Düngemitteln, granuliert werden.Fertilizer granules are customary manner, if desired in admixture with fertilizers, granulated.
Die erfindungsgemäßen Mittel enthalten in der Regel 1 bis 95 Gew.-%, vorzugsweise 2 bis 90 Gew.-% der erfindungsgemäßen herbiziden Salze (Wirkstoffe).As a rule, the compositions according to the invention contain 1 to 95% by weight, preferably 2 to 90% by weight, of the herbicidal salts (active substances) according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbarenIn wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. When emulsifiable
Konzentraten kann die Wirkstoffkonzentration etwa 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen etwa 2 bis 20 Gew.-%. Bei Granulaten hängt derConcentrates, the drug concentration may be about 5 to 80 wt .-%. Dusty formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. For granules depends on the
Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.Part of active ingredient content depends on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-,In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting,
Dispergier-, Emulgier-, Penetrations-, Lösungsmittel, Fülloder Trägerstoffe.Dispersing, emulsifying, penetrating, solvent, filling or excipients.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Konzentrate gegebenenfalls in üblicher Weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser. Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.For use, the commercially available concentrates are optionally diluted in a conventional manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules by means of water. Dusty and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
O -4O -4
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u. a. variiert die erforderliche Aufwandmenge. Sie kann innerhalb weiter Grenzen schwanken, z. B. zwischen 0,005 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,01 und 5 kg/ha.With the external conditions such as temperature, humidity, etc. varies the required application rate. It can vary within wide limits , eg. B. between 0.005 and 10.0 kg / ha or more active substance, but it is preferably between 0.01 and 5 kg / ha.
Auch Mischungen oder Mischformulierungen mit anderen Wirkstoffen, wie z. B. Insektiziden, Akariziden, Herbiziden, Düngemitteln, Wachstumsregulatoren oder Fungiziden sind gegebenenfalls möglich.Also mixtures or mixed formulations with other active ingredients, such as. As insecticides, acaricides, herbicides, fertilizers, growth regulators or fungicides may be possible.
In den folgenden Beispielen beziehen sich Prozentangaben auf das Gewicht, sofern nichts anderes angegeben ist.In the following examples, percentages are by weight unless otherwise specified.
Herstellungsbeispiele Allgemeine VorschriftProduction Examples General rule
Di3 Herbizid-Säure wird wie in den Tabellen angegeben in Wasser und/oder einem organischen Lösungsmittel gelöst und bei Temperaturen zwischen 25-50 C mit der betreffenden Base oder deren Gemisch in den gewünschten molaren Mengen tropfenweise versetzt. Nach beendeter Zugabe wird noch 10 Minuten nachgerührt. Man erhält eine leicht gefärbte Lösung. Bei schlechter Löslichkeit der entstandenen Salze ist der Einsatz von Lösevermittlern wie Isopropanol, Propylenglykol, Ethylenglykol, oder Polyglykole oder von Dimethylformamid zweckmäßig.Di3 herbicidal acid is dissolved in water and / or an organic solvent as indicated in the tables and mixed at temperatures between 25-50 C with the relevant base or mixture thereof in the desired molar amounts dropwise. After completion of the addition, stirring is continued for 10 minutes. This gives a slightly colored solution. With poor solubility of the resulting salts, the use of solubilizers such as isopropanol, propylene glycol, ethylene glycol, or polyglycols or of dimethylformamide is appropriate.
Nach dieser Verfahrensweise lassen sich die Salze der folgenden Beispiele herstellen.Following this procedure, the salts of the following examples can be prepared.
Beispiele für die Umsetzung der Verbindung XIIa und XIIb mit Aminkomponenten. Mengen berechnet für 100 g Lösung Examples of the reaction of the compounds XIIa and XIIb with amine components. Quantities calculated for 100 g of solution
Beispiel Nr.Example no.
Aminkomponenteamine component
Verbindung XIIa fg] Compound XIIa fg]
Aminkomponente WasserAmine component water
fgi M fgi M
Konz. Wirkstoffkonzentration [Gew.-%] Conc. Active substance concentration [% by weight]
) Molverhältnis Verbindung XIIa:Amin ^= 1:2) Molar ratio of compound XIIa: amine ^ = 1: 2
TABELLE 1 (Fortsetzung)TABLE 1 (continued)
Beispiel Aminkomponente Nr.Example Amine Component No.
Herbizid- Aminkompo- Wasser Lösungsvermittler Säure nente [g] [g] u. NetzmittelHerbicide Amine Compound Water Solubilizer Acid Nucleus [g] [g] u. wetting agent
Wirkstoffkonzentration fGew.-%1 Active ingredient concentration% by weight 1
Dodecylamindodecylamine
IlIl
8 g Ua 8 g Ha8 g and 8 g of Ha
Cocosfettamin + 2EO 10 g HaCoconut fat amine + 2EO 10 g Ha
8 88 8
22,222.2
g Dimethylformamid g Dimethylformamid u. g Nonylphenol + 10EO 6,7 g Propylenglykolmono-g dimethylformamide g dimethylformamide u. Nonylphenol + 10EO 6.7 g of propylene glycol mono-
methylether und 11,1 g Natrium-Alkylether-methyl ether and 11.1 g of sodium alkyl ether
sulfat (®Genapol LRO, 70 %ig in Wasser) 3,5 g PropylenglykolmonomethyletherSulfate (®Genapol LRO, 70% in water) 3.5 g of propylene glycol monomethyl ether
8 % 8 %8% 8%
10 %10%
7,8 %7.8%
Beispiele für die Umsetzung der Verbindung XIII mit Aminkomponenten Mengen berechnet für 100 g LösungExamples of the reaction of compound XIII with amine components. Quantities calculated for 100 g of solution
Aminkomponenteamine component
Verbindung XIII Compound XIII
m Aminkomponentem amine component
fglfgl
m Wasserm of water
Konz. Verbindung XIIIConc. Compound XIII
Molverhältnis Verbindung XIIIrAmin = 1:2Molar ratio of compound XIIIrAmin = 1: 2
TABELLE 2 (Fortsetzung) Beispiel Aminkomponente Nr.TABLE 2 (continued) Example Amine Component No.
1818
Verbindung Wasser Lösungs- und XIII [gl Netzmittel Compound water solution and XIII [g wetting agent
Wirkstoffkonzentrationdrug concentration
g Cocosfettamin + 2EO 19,3 g 9,7 g 20 g Isotridecanol + 6EO undg coconut fatty amine + 2EO 19.3 g 9.7 g 20 g isotridecanol + 6EO and
10 g Propylenglykolmonomethylether 10 g of propylene glycol mono methyl ether
19,3 %19.3%
41 g Cocosfettamin + 2E0 19,3 g 7,7 g 17 g Isotridecanol + 6EO, 9 g Polyglykol 200 und 6,0 Propylenglykolmono-41 g coconut fatty amine + 2E0 19.3 g 7.7 g 17 g isotridecanol + 6EO, 9 g polyglycol 200 and 6.0 propylene glycol mono-
methylethermethyl ether
19,3 %19.3%
30 g N,N,N',N'-Tetrakis-(2-hydroxypropyl) ethylendiamin30 g of N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine
29,6 g 15,6 g 8,0 g Propylenglykolmono-29.6 g 15.6 g 8.0 g propylene glycol mono
methylether und 16,8 g einer 40 %igen wäßrigen Lösung eines Na-SuIfobernsteinsäureestersmethyl ether and 16.8 g of a 40% aqueous solution of a Na-succinic acid ester
29,6 %29.6%
20,2 g Ν,Ν,Ν',N'-Tetrakis- 20,0 g (2-hydroxypropyl)-ethylendiamine 19,8 10,0 g Propylenglykolmethyl-20.2 g of Ν, Ν, Ν ', N'-tetrakis 20.0 g (2-hydroxypropyl) ethylenediamine 19.8 10.0 g of propylene glycol methyl
ether und 30,0 g Natrium-Alkylethersulfat (®Genapol LRO, %ig in Wasser) ether and 30.0 g of sodium alkyl ether sulfate (®Genapol LRO, % in water)
20,0 %20.0%
20,2 g Ν,Ν,Ν',N'-Tetrakis- 20,0 g (2-hydroxypropyl)-ethylendiamin und 5,0 g Cocosfettamin + 2EO 31,5 g 10,0 g Propylenglykolmonomethyl- 20 %20.2 g of Ν, Ν, Ν ', N'-tetrakis 20.0 g (2-hydroxypropyl) ethylenediamine and 5.0 g of coconut fatty amine + 2EO 31.5 g 10.0 g of propylene glycol monomethyl 20%
ether und 13,3 g Isotridecanol + 6EOether and 13.3 g isotridecanol + 6EO
40 g Cocosfettamin + 2EO 20 g 16,8 g Dimethylformamid, 10,5 g Nonylphenol + 10EO und 12,7 g ®Solvesso 20040 g coconut fatty amine + 2EO 20 g 16.8 g dimethylformamide, 10.5 g nonylphenol + 10EO and 12.7 g ®Solvesso 200
20 %20%
40 g Cocosfettamin + 2EO 20 g 16,8 g Dimethylformamid, 12,7 g ®Solvesso 200 und40 g coconut fatty amine + 2EO 20 g 16.8 g dimethylformamide, 12.7 g ®Solvesso 200 and
10,5olsotridecanol + 6EO ο10, 5olotridecanol + 6EO o
20 %20%
Beispiel 3.1Example 3.1
EC — Formulierung eines Diclofop-Salzes EC = wasseremulgierbares KonzentratEC formulation of a diclofop salt EC = water emulsifiable concentrate
14,6 g Diclofop werden mit14.6 g of diclofop are added
8,6 g Dodecylamin in 34,28 g Xylol8.6 g of dodecylamine in 34.28 g of xylene
17 Stunden auf 1300C erwärmt. Nach Abkühlen auf 22°C wird mit 19,05 g Cyclohexanon verdünnt und mit 19,05 g einer Mischung aus einem Calciumsalz einerHeated to 130 0 C for 17 hours. After cooling to 22 ° C is diluted with 19.05 g of cyclohexanone and with 19.05 g of a mixture of a calcium salt
chlorierten sekundären C-^-C-^g-Paraff insulfonsaure und ethoxyliertem Rizinusöl (36 EO) (®Emulsogen ITN) undchlorinated secondary C - ^ - C - g-paraffinsulfuric acid and ethoxylated castor oil (36 EO) (®Emulsogen ITN) and
4,76 g ethoxylierten 2,4,6-Tributylphenol (30 EO) (®Sapogenat T-300) versetzt.Add 4.76 g of ethoxylated 2,4,6-tributylphenol (30 EO) (®Satogenate T-300).
Biologische Beispiele Beispiel IBiological Examples Example I
Verschiedene Pflanzenarten wurden auf sandigem Lehmboden in Töpfen von 9 cm Durchmesser ausgesät und unter Gewächshausbedingungen angezogen, bis sie ein Stadium vonVarious plant species were sown on sandy loam soil in pots of 9 cm diameter and grown under greenhouse conditions until they reached a stage of
4-5 Blättern erreicht hatten. Dann wurden sie mit denHad reached 4-5 leaves. Then they were with the
erfindungsgemäßen Salzen besprüht, wobei ein Spritzvolumen von 300 1 Wasser/ha zur Anwendung kam. Die Pflanzen wurden sodann weitere 3-5 Wochen im Gewächshaus kultiviert. Anschließend wurde die herbizide Wirksamkeit im Vergleichsprayed salts according to the invention, wherein a spray volume of 300 1 water / ha was used. The plants were then cultivated in the greenhouse for another 3-5 weeks. Subsequently, the herbicidal activity was compared
zur unbehandelten Kontrolle visuell bonitiert. Als Vergleichsmittel wurden herkömmliche Formulierungen eingesetzt. Der Versuch wurde mit 2 Wiederholungen durchgeführt.visually scored for untreated control. Comparative agents used were conventional formulations. The experiment was carried out with 2 repetitions.
Pflanzenarten: SIAL = Sinapis albaPlant species: SIAL = Sinapis alba
CRSE = Chrysanthemum segetumCRSE = Chrysanthemum segetum
AVFA = Avena fatuaAVFA = Avena fatua
AGRE = Agropyron repensAGRE = Agropyron repens
CYDA = Cynodon dactylonCYDA = Cynodon dactylon
ν 3 4 5 3ν 3 4 5 3
Die Ergebnisse der Versuche sind in Ta.bel.le Ia - Ic dargestellt. Daraus wird die überlegene Wirksamkeit der erfindungsgemäßen Formulierungen gegenüber den Vergleichsformulierungen sichtbar.The results of the experiments are shown in Ta.bel.le Ia - Ic. From this, the superior efficacy of the formulations according to the invention over the comparison formulations is visible.
Tabelle Ia: Herbizide Wirkung verschiedenerTable Ia: Herbicidal action of various
erfindungsgemäßer Salze enthaltend Wirkstoffsalts according to the invention containing active ingredient
der Formel XIIIof formula XIII
(Bonitur 5 Wochen nach Applikation)(Rating 5 weeks after application)
Salzsalt
Dosis in Herbizide Wirksamkeit in % kg AS/ha AGRE CYDADose in herbicides Efficacy in% kg AS / ha AGRE CYDA
AS bedeutet hier wie in den folgenden Tabellen die eingesetzte Menge der Herbizid-Säure des betreffenden SalzesAS here means, as in the following tables, the amount of herbicidal acid of the salt in question
21 2 δ J. 5 3 321 2 δ J. 5 3 3
Tabelle Ib: Herbizide Wirkung verschiedener Salze der Verbindung XIIb (Bialaphos) (Bonitur 3 Wochen nach Behandlung)Table Ib: Herbicidal activity of various salts of compound XIIb (bialaphos) (scoring 3 weeks after treatment)
2 8 4 5]2 8 4 5]
Tabelle Ic: Herbizide Wirksamkeit verschiedenerTable Ic: Herbicidal activity of various
erfindungsgemäßer Salze von Glufosinate (Verbindung XIIa) bei Zusatz von Additiven (Bonitur 3 Wochen nach Applikation)salts of glufosinate according to the invention (compound XIIa) with addition of additives (rating 3 weeks after application)
X-060 = Isotridecanol + 5 Mol EO N-060 = Nonylphenol + 5 Mol EO LRO = LaurylpolyglykolethersulfatnatriumsalzX-060 = isotridecanol + 5 moles EO N-060 = nonylphenol + 5 moles EO LRO = lauryl polyglycol ether sulfate sodium salt
Die Konzentration der Additive X-060, N-060 und LRO beträgt jeweils 0,3 % bezogen auf das Spritzvolumen von 300 l/ha.The concentration of the additives X-060, N-060 and LRO is in each case 0.3% with respect to the spray volume of 300 l / ha.
In Topfen von 13 cm Durchmesser wurden verschiedene Pflanzenarten auf sandigem Lehmboden ausgesät und anschließend bei guten Wachstumsbedingungen bis zur Größe von 4-6 Blättern unter Freilandbedingungen angezogen. Dann wurden sie mit den verschiedenen erfindungsgemäßen Salzen der beanspruchten Herbizidwirkstoffe behandelt. Hierbei kam ein Sprühvolumen von 300 l/ha Wasser zur Anwendung. DieIn pots of 13 cm diameter, various plant species were sown on sandy loam soil and then grown under good growth conditions up to the size of 4-6 leaves under field conditions. Then they were treated with the various salts of the claimed herbicidal active ingredients according to the invention. Here, a spray volume of 300 l / ha of water was used. The
24 2 8 «l 5 8 324 2 8 «l 5 8 3
Pflanzen wurden nach der Herbizidbehandlung weitere 5 Wochen unter guten Wachstumsbedingungen im Freien kultiviert, und anschließend wurde die herbizide Wirkung im Vergleich zu unbehandelten Kontrollpflanzen visuell bonitiert, wobei die Schädigung der Pflanzen in Prozent geschätzt wurde. Es wurden zwei Wiederholungen durchgeführt.Plants were cultivated outdoors after the herbicidal treatment for another 5 weeks under good growth conditions, and then the herbicidal activity was scored vis-à-vis untreated control plants, with percent damage to the plants estimated. There were two repetitions.
Pflanzenarten: SIAL = Sinapis albaPlant species: SIAL = Sinapis alba
10 CRSE = Chrysanthemum segetum10 CRSE = Chrysanthemum segetum
HOVU = Hordeum vulgäre AGRE = Agropyron repens CYDA = Cynodon dactylonHOVU = Hordeum vulgar AGRE = Agropyron repens CYDA = Cynodon dactylon
15 Die Ergebnisse der Bonituren sind in Tabelle Ha15 The results of the assessments are shown in Table Ha
dargestellt. Sie zeigen die überlegene herbizide Wirkung der erfindungsgemäßen Salze. Darüber hinaus wirken einige Salze gegen grasartige Kulturpflanzen wie z.B. Gerste deutlich schwächer, als gegen breitblättrige, so daß sie selektiv in Getreidearten zur Bekämpfung von Unkräutern eingesetzt werden können.shown. They show the superior herbicidal activity of the salts according to the invention. In addition, some salts are active against grassy crops such as e.g. Barley is significantly weaker than broadleaf, so that they can be used selectively in cereals to control weeds.
Tabelle Ha: Herbizide Wirksamkeit und SelektivitätTable Ha: Herbicidal activity and selectivity
verschiedener Salze von Glufosinate 25 (Verbindung XIIa)various salts of glufosinate 25 (compound XIIa)
2 8 4 5 0 32 8 4 5 0 3
Dosis in Herbizide Wirksamkeit in % kg AS · SIAL CRSE HOVUDose in herbicidal activity in% kg AS · SIAL CRSE HOVU
Claims (9)
20CH 3 OH
20
25or (Ib)
25
Alkyl- oder Alkenylphenyl, Alkyl- oderR = a saturated or mono- or polyunsaturated aliphatic radical having 6-22 C atoms;
Alkyl or alkenylphenyl, alkyl or
X= Wasserstoff, Polyoxethylen mit 1-40 Mol EOeach containing 1-30 C atoms, preferably 8-12 C atoms, and
X = hydrogen, polyoxethylene with 1-40 moles of EO
p= unabhängig voneinander eine ganze Zahl von 2 bis 6,t
p = independently an integer from 2 to 6,
R4= (C1-C22)AIkYl, bevorzugt (C1-Cg)AIkYl bedeutet,with 1-40 PyO, preferably 4-12 PyO or a block polymer A and
R 4 = (C 1 -C 22 ) AlKyl, preferably (C 1 -Cg) AlKyl,
5 X= unabhängig voneinander Wasserstoff, PolyoxethylenC atoms and
5 X = independently hydrogen, polyoxethylene
R= ein gesättigter oder ein- oder mehrfachwherein
R = one saturated or one or more times
X7- unabhängig voneinander Wasserstoff, Polyoxethylenunsaturated aliphatic radical having 1-22 C atoms, and
X 7 - independently hydrogen, polyoxethylene
X = (C1-C1-)Alkyl, Polyoxethylen mit 1-65 EO, Polyoxpropylen mit 1-45 PyO oder ein Blockpolymerisat A bedeutet.10
X = (C 1 -C 1 -) alkyl, polyoxethylene with 1-65 EO, polyoxpropylene with 1-45 PyO or a block polymer A.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE3832147 | 1988-09-22 |
Publications (1)
Publication Number | Publication Date |
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DD284583A5 true DD284583A5 (en) | 1990-11-21 |
Family
ID=6363454
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DD89332837A DD284583A5 (en) | 1988-09-22 | 1989-09-20 | HERBICIDES AND METHOD FOR PRODUCING THE ACTIVE SUBSTANCES |
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EP (1) | EP0360181A2 (en) |
JP (1) | JPH02124846A (en) |
KR (1) | KR900004258A (en) |
AU (1) | AU4157689A (en) |
BR (1) | BR8904779A (en) |
DD (1) | DD284583A5 (en) |
HU (1) | HUT51859A (en) |
IL (1) | IL91697A0 (en) |
MY (1) | MY104908A (en) |
ZA (1) | ZA897205B (en) |
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IL101539A (en) * | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Non-hygroscopic mono-ammonium salts of n-phosphonomethyl glycine derivatives their preparation and pesticidal compositons containing them |
JP3853356B2 (en) * | 1994-06-02 | 2006-12-06 | 花王株式会社 | Agricultural efficacy enhancer, agrochemical efficacy enhancer composition, and method for enhancing agrochemical efficacy |
US5849663A (en) * | 1994-06-02 | 1998-12-15 | Kao Corporation | Enhancer for agricultural chemicals, enhancer composition for agricultural chemicals and method for enhancing the efficacy of agricultural chemical |
US6211139B1 (en) | 1996-04-26 | 2001-04-03 | Goldschmidt Chemical Corporation | Polyester polyquaternary compounds, compositions containing them, and use thereof |
DE69816988T2 (en) * | 1997-06-27 | 2004-07-22 | Flamel Technologies | METHOD AND COMPOSITIONS FOR PROMOTING THE BIOLOGICAL EFFECTIVENESS OF EXOGENIC CHEMICAL SUBSTANCES IN PLANTS |
EP1121341A1 (en) * | 1998-10-13 | 2001-08-08 | Goldschmidt Chemical Corporation | Polyester polyquaternary compounds, compositions containing them, and uses thereof |
ES2237202T3 (en) | 1998-11-30 | 2005-07-16 | Flamel Technologies | IMPROVEMENT OF THE BIOLOGICAL EFFECTIVENESS OF CHEMICAL SUBSTANCES EXOGENATED IN THE VEGETABLES. |
BR9916573A (en) * | 1998-12-23 | 2001-10-02 | Monsanto Technology Llc | Process and compositions to promote the biological effectiveness of exogenous chemicals in plants |
DE19953274A1 (en) * | 1999-11-05 | 2001-05-10 | Cognis Deutschland Gmbh | Emulsions |
RU2489857C2 (en) | 2006-12-06 | 2013-08-20 | Акцо Нобель Н.В. | Compatibility of preparations for herbicide compositions, containing salts of 2,4-(dichlorophenoxy)acetic acid |
EP2094083B1 (en) | 2006-12-06 | 2014-07-23 | Akzo Nobel N.V. | Alkylamidopropyl dialkylamine surfactants as adjuvants |
EP2296477B1 (en) * | 2008-04-18 | 2016-08-31 | Oxiteno S.A. Industria e Comercio | Herbicide formulation |
AU2011206563B2 (en) * | 2010-01-18 | 2015-01-22 | Basf Se | Compound comprising a pesticide and an alkoxylate of 2-propylheptyl amine |
UY39627A (en) | 2011-10-26 | 2022-03-31 | Monsanto Technology Llc | HERBICIDE SALTS OF CARBOXYLIC ACID |
US20130303369A1 (en) * | 2011-12-29 | 2013-11-14 | E. I. Du Pont De Nemours And Company | Fatty Amine Salts Of Herbicidal Pyrimidines |
AU2012382165B2 (en) | 2012-06-07 | 2016-11-17 | Shinko Chemical Co., Ltd. | Safety cap |
BR112015010075A2 (en) | 2012-11-05 | 2017-07-11 | Monsanto Technology Llc | auxin herbicidal mixtures |
-
1989
- 1989-09-16 EP EP89117188A patent/EP0360181A2/en not_active Withdrawn
- 1989-09-20 MY MYPI89001290A patent/MY104908A/en unknown
- 1989-09-20 KR KR1019890013494A patent/KR900004258A/en not_active Application Discontinuation
- 1989-09-20 IL IL91697A patent/IL91697A0/en unknown
- 1989-09-20 DD DD89332837A patent/DD284583A5/en not_active IP Right Cessation
- 1989-09-21 AU AU41576/89A patent/AU4157689A/en not_active Abandoned
- 1989-09-21 HU HU894915A patent/HUT51859A/en unknown
- 1989-09-21 BR BR898904779A patent/BR8904779A/en unknown
- 1989-09-21 JP JP1246234A patent/JPH02124846A/en active Pending
- 1989-09-21 ZA ZA897205A patent/ZA897205B/en unknown
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MY104908A (en) | 1994-06-30 |
HUT51859A (en) | 1990-06-28 |
BR8904779A (en) | 1990-05-01 |
ZA897205B (en) | 1990-06-27 |
AU4157689A (en) | 1990-03-29 |
JPH02124846A (en) | 1990-05-14 |
IL91697A0 (en) | 1990-06-10 |
KR900004258A (en) | 1990-04-12 |
EP0360181A2 (en) | 1990-03-28 |
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