CH639957A5 - IMIDAZOLINYLBENZOATE. - Google Patents
IMIDAZOLINYLBENZOATE. Download PDFInfo
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- CH639957A5 CH639957A5 CH828978A CH828978A CH639957A5 CH 639957 A5 CH639957 A5 CH 639957A5 CH 828978 A CH828978 A CH 828978A CH 828978 A CH828978 A CH 828978A CH 639957 A5 CH639957 A5 CH 639957A5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- Indole Compounds (AREA)
Description
Die Erfindung bezieht sich auf Imidazolinylbenzoate der Formel I: The invention relates to imidazolinyl benzoates of the formula I:
,coofu , coofu
(I) (I)
30 30th
35 35
40 40
45 45
50 50
Ri Ri
Ri Ri
R R
R R
55 55
worin wherein
X Wasserstoff, Ci-C3-Alkyl, Halogen oder Nitro bedeutet, C1-c4-Alkyl ist, X is hydrogen, Ci-C3-alkyl, halogen or nitro, is C1-c4-alkyl,
für Ci-C6-Alkyl, C3-C6-Cycloalkyl, C2-C4-Alkenyl, Phenyl, Halogenphenyl oder Benzyl steht, oder die Substituenten und R2 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind, Cj-Q-Cycloalkyl bedeuten, das gegebenen- 60 falls durch Methyl substituiert ist, represents Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl, halophenyl or benzyl, or the substituents and R2 together with the carbon atom to which they are attached mean Cj-Q-cycloalkyl, which optionally substituted by methyl,
Wasserstoff, Ci-Ci2-Alkyl, das gegebenenfalls mit einer Q-C-Alkoxygruppe oder einer C3-C6-Cycloalkylgruppe oder einer Phenylgruppe oder einer Furylgruppe oder 1 bis 3 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, c3-c5-Alkenyl, das gegebenenfalls mit 1 oder2C]-C3-Alkylgruppen oder einer Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, Hydrogen, Ci-Ci2-alkyl, which is optionally substituted with a QC-alkoxy group or a C3-C6-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, preferably chlorine, c3-c5-alkenyl, which is optionally substituted with 1 or 2C] -C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted,
65 65
C3-C5-Alkinyl, das gegebenenfalls mit 1 bis 2 C1-C3-Alkyl-gruppen oder einer Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, Benzyl, Cyclohexenylmethyl, Ethinylcyclohexyl, Ethinylalkyl, Pentadienyl oder C3-C6-Cycloalkyl, das gegebenenfalls mit 1 oder 2 Ci-C3-Alkylgruppen substituiert ist, oder ein salzbildendes Kation von Alkalimetallen, Ammonium oder aliphatischem Ammonium bedeutet, C3-C5-alkynyl, which is optionally substituted with 1 to 2 C1-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted with 1 or 2 Ci-C3-alkyl groups, or denotes a salt-forming cation of alkali metals, ammonium or aliphatic ammonium,
und, falls die Substituenten Rt sowie R2 nicht gleich sind, die optischen Isomeren hiervon sowie die Säureadditionssalze dieser Verbindungen, falls der Substituent R3 kein salzbildendes Kation bedeutet. and, if the substituents Rt and R2 are not the same, the optical isomers thereof and the acid addition salts of these compounds, if the substituent R3 is not a salt-forming cation.
Die Erfindung bezieht sich ferner auf ein herbizides Mittel zur Bekämpfung unerwünschter Pflanzenarten, das eine herbizid wirksame Menge eines Imidazolinylbenzoats der oben angegebenen Formel I als Wirkstoff enthält. The invention further relates to a herbicidal composition for controlling undesirable plant species which contains a herbicidally effective amount of an imidazolinyl benzoate of the formula I given above as active ingredient.
Ein solches herbizides Mittel kann entweder auf das Blattwerk unerwünschter Pflanzenarten oder auf den Boden, der Samen, Sämlinge oder Fortpflanzungsorgane solcher unerwünschter Pflanzenarten enthält, aufgebracht werden. Such a herbicidal composition can either be applied to the foliage of undesirable plant species or to the soil which contains seeds, seedlings or reproductive organs of such undesirable plant species.
Für die Verwendung als herbizide Mittel werden diej enigen Imidazolinylbenzoate der eingangs genannten Formel I bevorzugt, worin X Wasserstoff, Q-c3-Alkyl oder Halogen bedeutet, Rj C1-c3-Alkyl ist, R2 für Q-Q-Alkyl oder Cyclohexyl steht, oder die Substituenten Ri sowie R2 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind, Cyclohexyl oder Methylcy-clohexyl bedeuten, R3 Wasserstoff, Q-Cn- Alkyl, das gegebenenfalls durch eine Ci-C3-Alkoxygruppe oder eine C3-C6-Cyclo-alkylgruppe oder eine Phenylgruppe oder eine Furylgruppe oder For use as herbicidal agents, those imidazolinylbenzoates of the formula I mentioned at the outset are preferred, in which X is hydrogen, Q-C3-alkyl or halogen, Rj is C1-C3-alkyl, R2 is QQ-alkyl or cyclohexyl, or the substituents R 1 and R 2 together with the carbon atom to which they are attached mean cyclohexyl or methylcy-clohexyl, R 3 is hydrogen, Q-Cn-alkyl, which may be replaced by a Ci-C3-alkoxy group or a C3-C6-cyclo-alkyl group or a Phenyl group or a furyl group or
1 bis 3 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, c3-c5-Alkenyl, das gegebenenfalls durch 1 oder 2 Q-Q-Alkylgruppenoder eine Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, C3-C5-Alkinyl, das gegebenenfalls durch 1 bis 2 Ci-C3-Alkylgruppen oder eine Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, Benzyl, Cyclohexenylmethyl, Ethinylcyclohexyl, Ethinylalkyl, Pentadienyl oder C3-C6-Cycloalkyl, das gegebenenfalls durch 1 oder 2 C1-C3-Alkylgruppen substituiert ist, oder ein salzbildendes Kation von Alkalimetallen, Ammonium oder aliphatischem Ammonium bedeutet, und, falls die Substituenten Rj sowie R2 nicht gleich sind, die optischen Isomeren und Isomerengemische hiervon sowie die Säureadditionssalze dieser Verbindungen, falls der Substituent R3 kein salzbildendes Kation bedeutet. 1 to 3 halogen substituents, preferably chlorine, is substituted, c3-c5-alkenyl, which is optionally substituted by 1 or 2 QQ-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, C3-C5-alkynyl, which is optionally substituted by 1 up to 2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted by 1 or 2 C1-C3-alkyl groups or is a salt-forming cation of alkali metals, ammonium or aliphatic ammonium, and, if the substituents Rj and R2 are not the same, the optical isomers and isomer mixtures thereof and the acid addition salts of these compounds if the substituent R3 is not a salt-forming cation.
Stärker bevorzugt sind solche Verbindungen der Formel I, bei denen Rj Methyl bedeutet und R2 für Isopropyl steht, wobei sich zusätzlich hierzu folgende Untergruppen ergeben: Compounds of the formula I in which R 1 is methyl and R 2 is isopropyl are more preferred, and the following subgroups also result:
a. Verbindungen, bei denen X Wasserstoff oder Chlor ist und R3 Wasserstoff bedeutet, sowie die Alkalimetallsalze und die Ammoniumsalze hiervon, die optischen Isomeren hiervon und die Isomerengemische hiervon, a. Compounds in which X is hydrogen or chlorine and R3 is hydrogen, and the alkali metal salts and the ammonium salts thereof, the optical isomers thereof and the isomer mixtures thereof,
b. Verbindungen, bei denen X Wasserstoff, Methyl oder Chlor bedeutet und R3 für Ci-Ci2-Alkyl, das gegebenenfalls mit einer Q-Q-Alkoxygruppe oder einer Q-Q-Cycloalkylgruppe oder einer Phenylgruppe oder einer Furylgruppe oder 1 bis 3 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, steht, die optischen Isomeren hiervon, die Isomerengemische hiervon und die Säureadditionssalze hiervon, b. Compounds in which X is hydrogen, methyl or chlorine and R3 is Ci-Ci2-alkyl, which is optionally substituted with a QQ-alkoxy group or a QQ-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, preferably chlorine, stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof,
c. Verbindungen, bei denenX Wasserstoff, Methyl oder Chlor bedeutet und R3 für c3-c5-Alkenyl, das gegebenenfalls mit 1 oder 2 Ci-C3-Alkylgruppen oder einer Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, c. Compounds in which X is hydrogen, methyl or chlorine and R3 is c3-c5-alkenyl which is optionally substituted by 1 or 2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine,
steht, die optischen Isomeren hiervon, die Isomerengemische hiervon und die Säureadditionssalze hiervon, stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof,
d. Verbindungen, bei denen X Wasserstoff, Methyl oder Chlor bedeutet und R3 für c3-c5-Alkinyl, das gegebenenfalls mit 1 oder d. Compounds in which X is hydrogen, methyl or chlorine and R3 is c3-c5-alkynyl, optionally with 1 or
2 Ci-C3-Alkylgruppen oder einer Phenylgruppe oder 1 bis 2 Halogensubstituenten, vorzugsweise Chlor, substituiert ist, 2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted,
639 957 639 957
steht, die optischen Isomeren hiervon, die Isomerengemische hiervon und die Säureradditionssalze hiervon. stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof.
Diejenigen Imidazolinylbenzoate der Formel I, worin R3 nicht für Wasserstoff steht, werden erfindungsgemäss hergestellt, indem man ein Imidazoisoindoldion der später angegebenen Formel II mit einem entsprechenden Alkohol in Gegenwart eines Alkalimetalls oder einer Alkalimetallhydrids bei 20 bis 50° C umsetzt. Die Umsetzung wird vorzugsweise unter Inertgasschutz durchgeführt. Allgemein vermischt man hierzu zuerst ein Alkali-metall oder ein Alkalimetallhydrid mit einem entsprechenden Those imidazolinylbenzoates of the formula I in which R3 is not hydrogen are prepared according to the invention by reacting an imidazoisoindoldione of the formula II given later with a corresponding alcohol in the presence of an alkali metal or an alkali metal hydride at 20 to 50 ° C. The reaction is preferably carried out under inert gas protection. Generally, an alkali metal or an alkali metal hydride is first mixed with a corresponding one
Alkohol und vermischt das hiernach erhaltene Gemisch anschliessend mit dem jeweiligen Imidazoisoindoldion der Formel II. Alcohol and then mixes the mixture obtained thereafter with the respective imidazoisoindoldione of the formula II.
Als Inertgase lassen sich bei obigem Verfahren Stickstoff, 5 Argon oder Helium verwenden, wobei Stickstoff bevorzugt wird. In the above process, nitrogen, 5 argon or helium can be used as inert gases, nitrogen being preferred.
Beispiele für verwendbare Alkalimetalle oder Alkalimetallhydride sind Natrium, Natriumhydrid, Kalium, Kaliumhydrid, Lithium oder Lithiumhydrid. Examples of alkali metals or alkali metal hydrides which can be used are sodium, sodium hydride, potassium, potassium hydride, lithium or lithium hydride.
Die obigen Umsetzungen lassen sich formelmässig wie folgt io erläutern: The above implementations can be explained as follows:
(II) (II)
R30- R30-
ALkali-metall ALKALI metal
(III) (III)
(/^v^C00R3 (/ ^ v ^ C00R3
H H
Hierin haben X, Rj, R2 und R3 die oben angegebenen Bedeutungen. Herein, X, Rj, R2 and R3 have the meanings given above.
Bei den obigen Reaktionen wirkt der Alkohol sowohl als Reaktant als auch als Lösungsmittel. Man braucht daher kein zweites Lösungsmittel. Verwendet man bei der Umsetzung j e-doch einen teuren Alkohol und braucht man zur Erzielung optimaler Reaktionsbedingungen einen grossen Alkoholüber-schuss, dann empfiehlt sich der Zusatz eines wohlfeileren zweiten Lösungsmittels zum Reaktionsgemisch, wie Dioxan, Tetrahy-drofuran oder ein sonstiges nichtprotisches Lösungsmittel. Die Menge an dem Reaktionsgemisch zuzusetzendem nichtproti-schem Lösungsmittel kann ziemlich breit variiert werden, sie geht im allgemeinen jedoch nicht über das Vielfache der Menge In the above reactions, the alcohol acts both as a reactant and as a solvent. There is therefore no need for a second solvent. However, if an expensive alcohol is used in the reaction and a large excess of alcohol is required to achieve optimal reaction conditions, then it is advisable to add a cheaper second solvent to the reaction mixture, such as dioxane, tetrahydrofuran or another non-protic solvent. The amount of non-protic solvent to be added to the reaction mixture can be varied quite widely, but in general it does not exceed a multiple of the amount
25 25th
30 30th
35 35
an verwendetem Alkohol hinaus. Das Verhältnis aus zweitem Lösungsmittel und Alkohol, bei dem erfindungsgemäss gearbeitet werden kann, liegt daher zwischen 0,0:1 und 4,0:1. alcohol used. The ratio of second solvent and alcohol, which can be used according to the invention, is therefore between 0.0: 1 and 4.0: 1.
Diejenigen Verbindungen der Formel I, bei denen R3 Wasserstoff ist, werden hergestellt, indem man ein Imidazoisoindoldion der Formel II mit einem Überschuss an Chlorwasserstoffsäure, vorzugsweise in Gegenwart eines mit Wasser mischbaren Lösungsmittels, wie Tetrahydrofuran oder Dioxan, umsetzt. Diese Umsetzung führt zu einem Lactonhydrochlorid der im folgenden genannten Formel IV, aus dem man durch Behandeln mit einem Äquivalent Base, wie Natriumhydroxid, Kaliumhydroxid oder Natriumcarbonat, die entsprechende Säure erhält. Die Umsetzung läuft formelmässig wie folgt ab: Those compounds of formula I in which R3 is hydrogen are prepared by reacting an imidazoisoindoldione of formula II with an excess of hydrochloric acid, preferably in the presence of a water-miscible solvent, such as tetrahydrofuran or dioxane. This reaction leads to a lactone hydrochloride of the formula IV mentioned below, from which the corresponding acid is obtained by treatment with an equivalent base, such as sodium hydroxide, potassium hydroxide or sodium carbonate. The implementation proceeds formally as follows:
(II) (II)
(IV) (IV)
^T^COOH H ^ T ^ COOH H
60 60
NaOH NaOH
Die in obiger Weise erhaltene Imidazolinylbenzoesäure lässt sich dann in üblicher Weise in das j eweils gewünschte Alkalimetallsalz, Ammoniumsalz oder aliphatische Ammoniumsalz überführen. The imidazolinylbenzoic acid obtained in the above manner can then be converted in the customary manner into the alkali metal salt, ammonium salt or aliphatic ammonium salt desired in each case.
Zur Bildung eines Alkalimetallsalzes kann man die jeweilige Säure mit einer konzentrierten wässrigen Lösung des jeweiligen Alkalimetallhydroxids behandeln und dann in üblicher Weise das Wasser vom Reaktionsgemisch entfernen, vorzugsweise durch To form an alkali metal salt, the respective acid can be treated with a concentrated aqueous solution of the respective alkali metal hydroxide and then the water can be removed from the reaction mixture in a conventional manner, preferably by
65 65
(I) (I)
azeotrope Destillation mit einem organischen Lösungsmittel, wie Dioxan. azeotropic distillation with an organic solvent such as dioxane.
Die Ammoniumsalze oder die aliphatischen Ammoniumsalze lassen sich in ähnlicher Weise herstellen, wobei man abweichend davon jedoch die jeweilige Säure der Formel I teilweise in einem niederen Alkohol, wie Methanol, Ethanol oder Isopropanol, löst und die hierdurch erhaltene Lösung dann mit Ammoniak oder dem entsprechenden aliphatischen Amin behandelt. Im An- The ammonium salts or the aliphatic ammonium salts can be prepared in a similar manner, but, in deviation from this, the respective acid of the formula I is partially dissolved in a lower alcohol, such as methanol, ethanol or isopropanol, and the solution thus obtained is then dissolved in ammonia or the corresponding aliphatic Amine treated. In the arrival
639 957 639 957
schluss daran kann man das erhaltene Reaktionsgemisch einengen , den zurückbleibenden Feststoff mit Hexan behandeln und das Material schliesslich trocknen, wodurch man zu einem Ammoniumsalz oder einem aliphatischen Ammoniumsalz der Formel I gelangt. finally, the reaction mixture obtained can be concentrated, the remaining solid can be treated with hexane and the material can finally be dried, whereby an ammonium salt or an aliphatic ammonium salt of the formula I is obtained.
Als aliphatisches Ammonium kommen in Betracht: Monoal-kylammonium, Dialkylammonium, Trialkylammonium, Mono-alkenylammonium, Dialkenylammonium, Trialkenylammo-nium, Monoalkinylammonium, Dialkinylammonium, Trialkinylammonium, Monoalkanolammonium, Dialkanolam-monium oder Trialkanolammonium handelt, wobei diese aliphatischen Ammoniumgruppen 1 bis 18 Kohlenstoffatome enthalten. Suitable aliphatic ammonium are: monoalkylammonium, dialkylammonium, trialkylammonium, monoalkenylammonium, dialkenylammonium, trialkenylammonium, monoalkynylammonium, dialkinylammonium, monoalkanolammonium, or trialkanolammonium contains 1
Die erfindungsgemässen aliphatischen Ammoniumsalze können aus organischen Aminen mit einem Molekulargewicht von unter etwa300 hergestellt werden. Beispiele für solche Amine sind Methylamin, Ethylamin, n-Propylamin, Isopropylamin, n-Butylamin, Isobutylamin, s-Butylamin, n-Amylamin, Isoamyl-amin, Hexylamin, Heptylamin, Octylamin, Nonylamin, Decyl-amin, Undecylamin, Dodecylamin, Tridecylamin, Tetradecyl-amin, Pentadecylamin, Hexadecylamin, Heptadecylamin, Octa-decylamin, Methylethylamin, Methylisopropylamin, Methylhe- The aliphatic ammonium salts according to the invention can be prepared from organic amines with a molecular weight of less than about 300. Examples of such amines are methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine , Tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octa-decylamine, methylethylamine, methylisopropylamine, methylhe-
10 10th
15 15
20 20th
xylamin, Methylnonylamin, Methylpentadecylamin, Methyloc-tadecylamin, Ethylbutylamin, Ethylheptylamin, Ethyloctyl-amin, Hexylheptylamin, Hexyloctylamin, Dimethylamin, Diethylamin, Di-n-propylamin, Diisopropylamin, Di-n-amyla-min, Diisoamylamin, Dihexylamin, Diheptylamin, Dioctylamin, Trimethylamin, Triethylamin, Tri-n-propylamin, Triisopropyla-min, Tri-n-butylamin, Triisobutylamin, Tri-s-butylamin, Tri-n-amylamin, Ethanolamin, n-Propanolamin, Isopropanolamin, Diethanolamin, N,N-Diethylethanolamin, N-Ethylpropanola-min, N-Butylethanolamin, Allylamin, n-Butenyl-2-amin, n-Pen-tenyl-2-amin, 2,3-Dimethylbutenyl-2-amin, Dibutenyl-2-amin, n-Hexenyl-2-amin, und Propylendiamin. xylamine, methylnonylamine, methylpentadecylamine, methyloc-tadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-amylamine, diptylamine, diptylamine, diisoaminamine Trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-s-butylamine, tri-n-amylamine, ethanolamine, n-propanolamine, isopropanolamine, diethanolamine, N, N-diethylethanolamine, N-ethylpropanola-min, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl- 2-amine, and propylenediamine.
Die Verbindungen der obigenFormel I können Gemische aus zwei Stellungsisomeren sein, falls X eine andere Bedeutung als Wasserstoff hat, da die als Zwischenprodukte verwendeten Imidazoisoindoldione der Formel II ebenfalls Isomerengemische sind, falls X nicht für Wasserstoff steht. Die Ausgangsprodukte der Formel II lassen sich herstellen, indem man ein entsprechendes Phthalimidocarboxamid cyclisiert. Die Cyclisierung kann dabei an einer der beiden Imidcarbonylgruppen auftreten, wodurch ein Isomerengemisch entsteht, falls X eine andere Bedeutung als Wasserstoff hat: The compounds of formula I above can be mixtures of two positional isomers if X has a meaning other than hydrogen, since the imidazoisoindoldiones of formula II used as intermediates are also mixtures of isomers if X is not hydrogen. The starting products of formula II can be prepared by cyclizing an appropriate phthalimidocarboxamide. The cyclization can occur on one of the two imide carbonyl groups, which results in a mixture of isomers if X has a meaning other than hydrogen:
A A
c — conh-j I * c - conh-j I *
oder or
oh oder h oh or h
,4" , 4 "
und and
Die Substituenten Rj, R2 und X haben darin die oben angegebenen Bedeutungen, mit der Ausnahme, dass X nicht für Wasserstoff stehen kann. The substituents Rj, R2 and X have the meanings given above, with the exception that X cannot stand for hydrogen.
Die Imidazolinylbenzoate der obigen Formel I können ferner auch tautomer sein. Sie sind der Einfachheit halber zwar durch goor. The imidazolinyl benzoates of formula I above can also be tautomeric. They are through goor for simplicity.
x- x-
45 45
Die Substituenten X, Rj, R2 und R3 haben darin die oben angegebenen Bedeutungen. Unter der Formel I werden daher auch beide isomeren Formen der Imidazolinylbenzoate verstanden. The substituents X, Rj, R2 and R3 have the meanings given above. Formula I is therefore also understood to mean both isomeric forms of imidazolinyl benzoates.
Die Verbindungen sind amphoter. Sie lösen sich sowohl in sauren als auch in basischen wässrigen Lösungen, wobei sich bei Behandlung mit starken Säuren, insbesondere starker Mineralsäure, wie Chlorwasserstoffsäure, Schwefelsäure oderBromwas-serstoffsäure, die Säureadditionssalze der Imidazolinylbenzoate der Formel I bilden. The connections are amphoteric. They dissolve in both acidic and basic aqueous solutions, the acid addition salts of the imidazolinylbenzoates of the formula I being formed on treatment with strong acids, in particular strong mineral acid, such as hydrochloric acid, sulfuric acid or bromohydric acid.
Bedeuten bei den Imidazolinylbenzoaten der Formel I die Substituenten Ri und R2 verschiedene Gruppen, dann ist das If the substituents R 1 and R 2 in the imidazolinyl benzoates of the formula I mean different groups, then that is
60 60
eine einzelne Struktur mit der Formel I bezeichnet, können jedoch in einer der beiden folgenden isomeren Formen vorkommen: denotes a single structure with the formula I, but can occur in one of the following two isomeric forms:
Kohlenstoffatom, an das diese Gruppen gebunden sind, ein asymmetrisches Kohlenstoffatom. Solche Verbindungen kommen daher (genauso wie ihre Zwischenprodukte) in d- und 1-Formen sowie in dl-Formen vor. Carbon atom to which these groups are attached is an asymmetric carbon atom. Such compounds therefore (as well as their intermediates) occur in d and 1 forms as well as in dl forms.
Zur Herstellung der jeweiligen d- oder 1-Form setzt man das jeweilige optisch aktive d- oder 1-Imidazoisoindoldion der Formel II mit dem entsprechenden Alkohol der Formel III um, wodurch man zum entsprechenden d- oder 1-Imidazolinylbenzoat 65 der Formel I gelangt. To prepare the respective d- or 1-form, the respective optically active d- or 1-imidazoisoindoldione of the formula II is reacted with the corresponding alcohol of the formula III, which gives the corresponding d- or 1-imidazolinylbenzoate 65 of the formula I.
Die Imidazoisoindoldione der Formel II stellen Zwischenprodukte zur Herstellung der erfindungsgemässen Imidazolinylbenzoate dar und werden in US-PS 4017510 beschrieben. The imidazoisoindoldiones of the formula II are intermediates for the preparation of the imidazolinylbenzoates according to the invention and are described in US Pat. No. 4,017,510.
639 957 639 957
Die erfindungsgemässen Verbindungen sind äusserst wirksame herbizide Mittel zur Bekämpfung einkeimblättriger Pflanzen, Riedgräser (Cyperacae) und zweikeimblättriger Pflanzen. Sie können zur Nachauflaufbekämpfung unerwünschter Pflanzenarten verwendet werden, indem man das Blattwerk solcher Pflanzen mit einer herbizid wirksamen Menge derartiger Verbindungen behandelt, oder sie lassen sich auch zur Vorauflaufbekämp-fung unerwünschter Pflanzen einsetzen, indem man auf den Boden, der Samen, Sämlinge oder Fortpflanzungsorgane der unerwünschten Pflanzen enthält, eine herbizid wirksame Menge des jeweiligen Wirkstoffs aufträgt. Da die erfindungsgemässen Imidazolinylbenzoate der Formel I in Wasser sehr begrenzt löslich sind, werden sie im allgemeinen als Spritzpulver, emul-gierbare Konzentrate oder fliessfähige Flüssigkeiten formuliert, die man dann zum Versprühen normalerweise in Wasser oder einem sonstigen wohlfeilen flüssigen Verdünnungsmittel disper-giert. Die erfindungsgemässen Verbindungen können ferner auch als Granulate formuliert werden, die im allgemeinen etwa 10 bis 15 Gew.-% Wirkstoff enthalten. The compounds according to the invention are extremely effective herbicidal compositions for controlling monocotyledonous plants, sedge grasses (Cyperacae) and dicotyledonous plants. They can be used to control the emergence of undesirable plant species by treating the foliage of such plants with a herbicidally active amount of such compounds, or they can also be used to control the emergence of undesirable plants by applying to the soil, seeds, seedlings or reproductive organs contains unwanted plants, applies a herbicidally effective amount of the respective active ingredient. Since the imidazolinylbenzoates of the formula I according to the invention have very limited solubility in water, they are generally formulated as wettable powders, emulsifiable concentrates or free-flowing liquids, which are then normally dispersed in water or another cheap liquid diluent for spraying. The compounds according to the invention can also be formulated as granules which generally contain about 10 to 15% by weight of active ingredient.
Zur Herstellung eines Spritzpulvers vermischt man beispielsweise 25 bis 80 Gew.-% des jeweiligen Imidazolinylbenzoats, 2 bis 5 Gew.-% eines oberflächenaktiven Mittels, wie Natrium-N-methyl-N-oleyltautrat, Alkylphenoxypolyoxyethylenethanol oder Natriumalkylnaphthalinsulfonat, 5 bis 10 Gew.-% eines Dispergiermittels, wie hochgereinigtes Natriumlignosulfonat, und 25 bis 63 Gew.-% eines feinteiligen Trägers, wie Kaolin, Attapulgit oder Diatomeenerde, miteinander. To produce a wettable powder, for example, 25 to 80% by weight of the respective imidazolinylbenzoate, 2 to 5% by weight of a surface-active agent, such as sodium N-methyl-N-oleyltautrate, alkylphenoxypolyoxyethylene ethanol or sodium alkylnaphthalenesulfonate, 5 to 10% by weight are mixed. % of a dispersant, such as highly purified sodium lignosulfonate, and 25 to 63% by weight of a finely divided carrier, such as kaolin, attapulgite or diatomaceous earth, with one another.
Eine in obiger Weise hergestellte typische Formulierung setzt sich wie folgt zusammen: A typical formulation produced in the above way is composed as follows:
50 Gew.-% 2-Propinyl-o-(5-isopropyl-5-methyl-4-oxo-2-imi-dazolin-2-yl)-benzoat, 3 Gew.-% Natrium-N-methyl-N-oleoyl-tautrat, 10 Gew.-% Natriumlignosulfonat und 37 Gew.-% Kaolin. 50% by weight of 2-propynyl-o- (5-isopropyl-5-methyl-4-oxo-2-imi-dazolin-2-yl) benzoate, 3% by weight of sodium N-methyl-N- oleoyl tautrate, 10% by weight sodium lignosulfonate and 37% by weight kaolin.
Fliessfähige flüssige Formulierungen lassen sich herstellen, indem man etwa 40 bis 60 Gew.-% eines Imidazolinylbenzoats der Formel 1,2 bis 3 Gew.-% des Natriumsalzes von kondensierter Naphthalinsulfonsäure, 2 bis 3 Gew.-% eines gebildeten Tons, 2 Gew.-% Propylenglykol und 54 bis 32 Gew.-% Wasser miteinander vermahlt. Flowable liquid formulations can be prepared by mixing about 40 to 60% by weight of an imidazolinyl benzoate of the formula 1.2 to 3% by weight of the sodium salt of condensed naphthalenesulfonic acid, 2 to 3% by weight of a clay formed, 2% by weight. -% propylene glycol and 54 to 32 wt .-% water ground together.
Zur Herstellung eines entsprechenden Granulats kann man den jeweiligen Wirkstoff in einem Lösungsmittel lösen oder dispergieren und den Wirkstoff dann auf einen sorptionsfähigen oder nichtsorptionsfähigen Träger, wie Attapulgit, Maiskolbengrütze, Bimsstein oder Talkum, aufbringen. To produce a corresponding granulate, the respective active ingredient can be dissolved or dispersed in a solvent and the active ingredient can then be applied to a sorptive or non-sorptive carrier, such as attapulgite, corncob groats, pumice stone or talc.
Die Imidazolinylverbindungen der Formel I sind, wie oben angegeben, wirksame Vorauflaufherbizide. Sie eignen sich zur Bekämpfung breitblättriger Unkräuter und Gräser, wenn man den Boden, der Samen, Sämlinge oder Fortpflanzungsorgane breitblättriger Unkräuter, Riedgräser oder Graspflanzen enthält, mit Wirkstoffmengen von 0,07 bis 11,2 kg/ha behandelt. As indicated above, the imidazolinyl compounds of the formula I are effective pre-emergence herbicides. They are suitable for controlling broad-leaved weeds and grasses if the soil, seeds, seedlings or reproductive organs of broad-leaved weeds, sedge grasses or grass plants are treated with active compound amounts of 0.07 to 11.2 kg / ha.
Die den erfindungsgemässen Verbindungen eignen sich ferner zur Bekämpfung breitblättriger Unkräuter, Riedgräser und Graspflanzen, wenn man das Blattwerk derartiger Pflanzen mit Wirkstoffmengen von etwa 0,28 bis 11,2 kg/ha behandelt. The compounds according to the invention are also suitable for controlling broad-leaved weeds, sedge grasses and grass plants if the foliage of such plants is treated with active compound amounts of about 0.28 to 11.2 kg / ha.
Mit den erfindungsgemässen Verbindungen lassen sich zwar die verschiedensten Pflanzenarten wirksam bekämpfen, sie unterscheiden sich von den bekannten Herbiziden jedoch dadurch, dass sie sich besonders gut zur Bekämpfung bestimmter Cyperacaen , insbesondere Riedgräser, in verhältnismässig niedrigen A wide variety of plant species can be effectively combated with the compounds according to the invention, but they differ from the known herbicides in that they are particularly good at combating certain cyperaceans, in particular reed grasses, at relatively low levels
Anwendungskonzentrationen einsetzen lassen. Die Verbindungen der Formel I haben sich daher in der Praxis bei Vorauflaufbe-handlungen in Wirkstoffmengen von 0,14 bis 11,2 kg/ha als besonders wirksame Mittel zur Bekämpfung von Riedgräsern 5 erwiesen. Selbstverständlich kann zur Bekämpfung von Riedgräsern und anderen einjährigen Pflanzen auch mit höheren Anwendungsmengen der Verbindungen der Formel I gearbeitet werden, wenn der Bestand an Cyperacaen oder einjährigen Pflanzen besonders stark ist. Allow application concentrations to be used. In practice, the compounds of the formula I have therefore proven to be particularly effective agents for combating reed grasses 5 in pre-emergence treatments in amounts of active ingredient from 0.14 to 11.2 kg / ha. To control reed grasses and other annual plants, it is of course also possible to use higher amounts of the compounds of the formula I if the stock of cyperaceas or annual plants is particularly strong.
10 Unter solchen Bedingungen lassen sich die Imidazolinylbenzoate der Formel I zur Vorauflaufbehandlung oder zur Nachauf-laufbehandlung in Mengen von bis zu 25 kg/ha anwenden. 10 Under such conditions, the imidazolinyl benzoates of the formula I can be used for pre-emergence treatment or for post-emergence treatment in amounts of up to 25 kg / ha.
Zu Cyperacaen, die sich mit den erfindungsgemässen Imidazo-linylderivaten bekämpfen lassen, gehören purpurnes Cypergras 15 (Cyperus rotundus L.), gelbes Cypergras (Cyperus esulentus L.), falsches Cypergras (Cyperus strigosus) sowie die Flachseggen, Schirmpflanzen und Kyllinga. Cyperacaen that can be controlled with the imidazoline derivatives according to the invention include purple cypergrass 15 (Cyperus rotundus L.), yellow cypergrass (Cyperus esulentus L.), false cypergrass (Cyperus strigosus) and the flat sedge, umbrella plants and Kyllinga.
Die Erfindung wird anhand der folgenden Beispiele weiter erläutert. The invention is further illustrated by the following examples.
20 20th
Beispiel 1 example 1
2-Propionyl-o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)- 2-propionyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -
benzoat benzoate
25 25th
Man gibt 12,5 ml Propargylalkohol zu0,l g einer 50%igen Suspension von Natriumhydrid in Mineralöl. Der Zusatz erfolgt unter Stickstoffschutz, wobei man das Reaktionsgemisch rührt und durch äussere Kühlung auf 20 bis 25° C hält. Nach etwa 1 bis 2 30 Stunden ist die Bildung des Natriumsalzes von Propargylalkohol beendet. Die Lösung wird dann mit 5,0 g 3-Isopropyl-3-methyl-5H-imidazo[2,l-a]isoindol-2(3H) ,5-dion versetzt und das Reaktionsgemisch über Nacht unter Stickstoffschutz bei Raumtemperatur gerührt. Eine anschliessende dünnschichtchromatographi-35 sehe Untersuchung zeigt, dass die Umsetzung unvollständig ist, und das Reaktionsgemisch wird daher mit weiteren 50 mg einer 50%igen Suspension von Natriumhydrid in Mineralöl versetzt. Das Reaktionsgemisch wird über Nacht gerührt, worauf man es auf 5° C kühlt und mit 0,7 ml 3 normaler Chlor wasserstoffsäure versetzt. Sodann verdünnt man das Reaktionsgemisch mit Methylenchlorid, wäscht das Ganze mit Wasser, trocknet die organische Schicht und engt sie unter Vakuum ein. Der hierbei anfallende kristalline Rückstand wird mit Hexan in einen Filtriertrichter übertragen und an der Luft getrocknet, wodurch man zu 6,02 g 2-Propinyl-o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoat gelangt, das bei 131 bis 144°C schmilzt. Durch Umkristallisieren dieses Materials aus Aceton-Hexan gelangt man zu einem reinen Produkt, das bei 145 bis 147°C schmilzt. 12.5 ml of propargyl alcohol are added to 0.1 g of a 50% suspension of sodium hydride in mineral oil. The addition is carried out under nitrogen protection, the reaction mixture being stirred and kept at 20 to 25 ° C. by external cooling. After about 1 to 2 30 hours, the formation of the sodium salt of propargyl alcohol has ended. The solution is then mixed with 5.0 g of 3-isopropyl-3-methyl-5H-imidazo [2, l-a] isoindole-2 (3H), 5-dione and the reaction mixture is stirred overnight under nitrogen protection at room temperature. A subsequent thin-layer chromatography study shows that the reaction is incomplete and the reaction mixture is therefore mixed with a further 50 mg of a 50% suspension of sodium hydride in mineral oil. The reaction mixture is stirred overnight, whereupon it is cooled to 5 ° C. and mixed with 0.7 ml of 3 normal hydrochloric acid. The reaction mixture is then diluted with methylene chloride, the whole is washed with water, the organic layer is dried and concentrated in vacuo. The resulting crystalline residue is transferred to a filter funnel with hexane and air-dried, yielding 6.02 g of 2-propynyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazoline-2- yl) benzoate reaches, which melts at 131 to 144 ° C. By recrystallizing this material from acetone-hexane, a pure product is obtained which melts at 145 to 147 ° C.
40 40
50 50
Beispiel 2 Example 2
Herstellung von Imidazolinylbenzoaten Nach dem in Beispiel 1 beschriebenen Verfahren werden die im folgenden angegebenen Imidazolinylbenzoate hergestellt, 55 indem man statt Propargylalkohol den j eweils angegebenen Alkohol verwendet und statt 3-Isopropyl-3-methyl-5H-imida-zo[2, l-a]-isoindol-2(3H)-5-dion das jeweils genannte Imidazoisoindoldion einsetzt. Die Umsetzung läuft formelmässig wie folgt ab: Preparation of Imidazolinylbenzoates The imidazolinylbenzoates given below are prepared by the process described in Example 1, 55 by using the alcohol indicated in each case instead of propargyl alcohol and instead of 3-isopropyl-3-methyl-5H-imida-zo [2, la] - isoindol-2 (3H) -5-dione uses the respective imidazoisoindoldione. The implementation proceeds formally as follows:
60 60
+ FUOR + FUOR
!_• ! _ •
IN d.i. IN d.i.
COOR. COOR.
639 957 639 957
8 8th
r, r,
r2 r2
ch, ch,
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3), ch (ch3),
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3> ch (ch3>
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3), ch (ch3),
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch,ch2ch3 / \ ch, ch2ch3 / \
ch3 ch3
-(ch2)5- - (ch2) 5-
-ch(ch3)ch2ch2ch2ch2- -ch (ch3) ch2ch2ch2ch2-
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
ch3 ch3
-ch(ch3), -ch (ch3),
ch3 ch3
-CH(ch3)o ch(ch3> -CH (ch3) o ch (ch3>
-ch(ch3)2 -ch (ch3) 2
-(ch2)5- - (ch2) 5-
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3), ch (ch3),
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)-, ch (ch3) -,
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3), ch (ch3),
ch3 ch3
ch(ch3), ch (ch3),
R3 R3
X X
Schmelzpunkt, °C Melting point, ° C
-ch,ch,ch3 -ch, ch, ch3
-ch22c6h5 -ch22c6h5
-(ch2)7ch3 -(ch2)uch3 - (ch2) 7ch3 - (ch2) uch3
-ch2ch=ch, -ch2ch = ch,
-ch3 -ch3
-c(ch3>ch=ch2 -c(ch3)o=ch -ch(ch3), -c (ch3> ch = ch2 -c (ch3) o = ch -ch (ch3),
-c(ch3)3 -c (ch3) 3
-ch2ch3 -ch2ch3
-ch(ch3)c=ch -ch2c(c1)=ch2 -ch (ch3) c = ch -ch2c (c1) = ch2
-ch2ch2c=ch -ch2ch2c = ch
-ch(ch3)ch=ch2 -c(ch3)2ch=ch2 -ch (ch3) ch = ch2 -c (ch3) 2ch = ch2
-c(ch3)2ch=ch2 -c(ch3)2ch=ch, -c (ch3) 2ch = ch2 -c (ch3) 2ch = ch,
-ch2c=ch -ch2c = ch
-^ch(ch3)-c(ch3)=ch, - ^ ch (ch3) -c (ch3) = ch,
-ch2ch=chch3 -ch2ch = chch3
-ch2c(ch3)=ch2 -ch2ch=c(ch3)2 -ch2c (ch3) = ch2 -ch2ch = c (ch3) 2
-CH. -CH.
<I> <i>
-CH(CH=CH2)2 -CH(CH3)-CH=CHCH3 -CH (CH = CH2) 2 -CH (CH3) -CH = CHCH3
-ch3 -ch3 -ch3 -ch3
-CH2C(CH3)3 -CH2C (CH3) 3
-C18H37-n -C18H37-n
-CH2CH2OCH3 -CH2CH2OCH3
-ch2-^ -ch2- ^
-C6H13-n ch3 I -C6H13-n ch3 I
-c-c2h5 ch3 -c-c2h5 ch3
-ch,ch,oc2h5 -ch2ch=ch-c6h5 -ch2-c=c-c6h5 -ch2-c=c-ch3 -ch, ch, oc2h5 -ch2ch = ch-c6h5 -ch2-c = c-c6h5 -ch2-c = c-ch3
- ch-<! - ch- <!
ch3 ch3
-CHi-C=C-C7hi5-n -CHi-C = C-C7hi5-n
-ch2cci3 -ch2cci3
-C(C,HS)2CH=CH2 -C (C, HS) 2CH = CH2
qh(ch3)2 qh (ch3) 2
-o -O
"CH3 "CH3
ce ck ce ck
Cl Cl
-ch2-c=ch2 -ch3 -ch2-c = ch2 -ch3
-ch2-c=ch -ch2-c = ch
H H H H H H H H H H H H H H H H H H H H H H
H H H H H H H H H H
H H H H H H H H H H H H H H H H
H H
H H H H H H H H H H H H H H
H H H H
H H
H H H H H H H H
H H
H H H H H H
H H
H H
120-121,5 (Zersetzung) 110-113 (Zersetzung) 120-121.5 (decomposition) 110-113 (decomposition)
73-75 (Zersetzung) 62,5-64,5 (Zersetzung) 109-111,5 (Zersetzung) 117-118 115,5-117,5 115-116 73-75 (decomposition) 62.5-64.5 (decomposition) 109-111.5 (decomposition) 117-118 115.5-117.5 115-116
121-122,5 139,5-141 123-124,5 121-122.5 139.5-141 123-124.5
97-104 97-104
114-116 127-128 114-116 127-128
94—98 (Zersetzung) 103,5-107 (Zersetzung) 94-98 (decomposition) 103.5-107 (decomposition)
115-120 (Zersetzung) 133,5-134,5 (Zersetzung) 168-171 (Zersetzung) 115-120 (decomposition) 133.5-134.5 (decomposition) 168-171 (decomposition)
85-94 (Zersetzung) 101-112 (Zersetzung) 91-102 (Zersetzung) 107-111 85-94 (decomposition) 101-112 (decomposition) 91-102 (decomposition) 107-111
100-106 (Zersetzung) 100-106 (decomposition)
78-87 (Zersetzung) 89-107 (Zersetzung) 78-87 (decomposition) 89-107 (decomposition)
146-147 164-165 146-147 164-165
147-148 147-148
79-81,5 87,5-92,5 79-81.5 87.5-92.5
122-125 84-86 122-125 84-86
87-89 87-89
99-100 120-125 134,5-138 125-128 99-100 120-125 134.5-138 125-128
4 (5) CH3 4 (5) CH3 4 (5) CH3 4 (5) CH3 4 (5) CH3 4 (5) CH3
95,98 95.98
94-96,5 143-145 111,5-115,5 94-96.5 143-145 111.5-115.5
74-78 74-78
168-169 168-169
128-130 143-151 154-159 128-130 143-151 154-159
9 9
639 957 639 957
Ri Ri
R2 R2
R3 R3
X X
Schmelzpunkt, °C Melting point, ° C
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch(ch3)2 ch (ch3) 2
-c-ch=ch2 -c-ch = ch2
h H
153-157,5 153-157.5
ch3 ch3 ch3 ch3 ch3 ch3
ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3
ch(ch3)2 ch (ch3) 2
(+)-Isomer ch(ch3)2 (+) - Isomer ch (ch3) 2
(-)-Isomer ch(ch3)2 (-) - Isomer ch (ch3) 2
(+)-Isomer ch(ch3> ch(ch3), ch(ch3)2 ch(ch3), ch(ch3)2 (+) - Isomer ch (ch3> ch (ch3), ch (ch3) 2 ch (ch3), ch (ch3) 2
ch(ch3)2 ch (ch3) 2
-c2h5 -c2h5
-ch2c=ch -ch2-c=ch2 -ch2c = ch -ch2-c = ch2
ci ci
-ch(ch3)ch=chch3 -ch (ch3) ch = chch3
-ch3 -ch3
-ch2-c=ch -ch2-c = ch
-ch2-c=c-ch2oh -ch2-c = c-ch2oh
-ch2-c=ch2 -ch2-c = ch2
H H H H H H
4 (5) CH3 3 (6) Cl 3 (6) Cl H 4 (5) CH3 3 (6) Cl 3 (6) Cl H
3 (6) Cl 3 (6) Cl
106-108 134-135 120-122 106-108 134-135 120-122
95-111 162-166 164-166 132-134 154-160 95-111 162-166 164-166 132-134 154-160
ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3
ch(ch3)2 ch(ch3)2 ch(ch3)2 ch (ch3) 2 ch (ch3) 2 ch (ch3) 2
c,h5 c, h5
c2h5 c2h5
c2h5 c2h5
CI CI
-ch2-ch2 -ch2-ch2
-ch(ch3)ch=ch-ch3 -ch (ch3) ch = ch-ch3
-c2h5 -ch3 -c2h5 -ch3
-ch2-c=ch -ch2-c=ch2 -ch2-c = ch -ch2-c = ch2
H H
3 (6) Cl 3 (6) N02 H H H 3 (6) Cl 3 (6) N02 H H H
166-169 161-163 156-157 135-136 137-139 125-126 166-169 161-163 156-157 135-136 137-139 125-126
ch3 ch3
ch(ch3)2 ch (ch3) 2
CI CI
-ch2-c=chc1 -ch2-c = chc1
H H
107-114 107-114
ch3 ch3 ch3 ch3
c,h5 c, h5
ch(ch3)2 ch (ch3) 2
ci ci
-ch(ch3)ch=chch3 -ch (ch3) ch = chch3
-ch2-c=ch2 -ch2-c = ch2
1 1
H H
3 (6) N02 3 (6) N02
119-121 161-162 119-121 161-162
ch3 ch3
ch(ch3)2 ch (ch3) 2
CI CI
ch3 ch3
-c-ch=ch2 -c-ch = ch2
H H
73-79 73-79
ch3 ch3
c2h5 c2h5
1 1
c2h5 ch3 c2h5 ch3
-c-ch=ch, -c-ch = ch,
1 1
H H
127-128 127-128
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 -c-ch=ch ch (ch3) 2 -c-ch = ch
H H
122-122,5 122-122.5
ch3 c2h5 ch3 c2h5
GH, C2H5 GH, C2H5
ch(ch3), ch(ch3)2 ch(ch3)o ch(ch3)2 ch (ch3), ch (ch3) 2 ch (ch3) o ch (ch3) 2
ch(ch3), ch (ch3),
-c2h5 -ch3 -c2h5 -ch3
-ch2-c=ch -ch2-c=ch2 -ch2-c = ch -ch2-c = ch2
4 (5) Cl H H H 4 (5) Cl H H H
112-138 139-140 147-149 134-135 112-138 139-140 147-149 134-135
ch3 ch3
ch, ch,
ch3 ch3
ch(ch3), ch(ch3), ch(ch3)2 ch (ch3), ch (ch3), ch (ch3) 2
ci ci
-chi-c=c=ch -ch(ch3)ch=chch3 -ch,-c=ch, -chi-c = c = ch -ch (ch3) ch = chch3 -ch, -c = ch,
" 1 " 1
4 (5) Cl 4 (5) Cl 4 (5) Cl 4 (5) Cl 4 (5) Cl 4 (5) Cl
177-187 177-187
01 01
01 01
ch3 ch3
ch(ch3)2 ch (ch3) 2
1 1
CI CI
CH=cht 1 CH = cht 1
H H
01 01
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch-c=ch ch3 -ch-c = ch ch3
-c-CH=cht -c-CH = cht
1 1
ch3 ch3
4 (5) Cl 4 (5) Cl
01 01
639 957 639 957
10 10th
r> r>
R: R:
r3 r3
X X
Schmelzpunkt, °C Melting point, ° C
CH, CH,
CH(CH3)2 CH (CH3) 2
H H
4 (5) Cl 4 (5) Cl
177-179 177-179
CH, CH,
C,H, C, H,
H H
H H
195-197 195-197
C,H, C, H,
CH(CH,)2 CH (CH,) 2
H H
H H
179-180 179-180
CH, CH,
CH(CH3h CH (CH3h
H H
3 (6) Cl 3 (6) Cl
154-156 154-156
CH, CH,
CH(CH3> CH (CH3>
C2H5 C2H5
4 (5) CH3 4 (5) CH3
CHj CHj
CH(CH3)2 CH (CH3) 2
C3Ht-ii C3Ht-ii
4 (5) CH3 (4 oder 5) 4 (5) CH3 (4 or 5)
CH, CH,
CH(CH3)2 CH (CH3) 2
C3Hr-n C3Hr-n
4 (5) CH3 (4 oder 5) 4 (5) CH3 (4 or 5)
ch3 ch3
CH(CH3)2 CH (CH3) 2
C3Hr-n C3Hr-n
4 (5) CH3 (4 oder 5) 4 (5) CH3 (4 or 5)
CHJ CHJ
CH(CH3)2 CH (CH3) 2
CH(CH3)2 CH (CH3) 2
4 (5) CH3 4 (5) CH3
15 15
Beispiel 3 Example 3
1, l-Dimethylallyl-o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoat-hydrochlorid 1, l-Dimethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate hydrochloride
.cooc(ch3)2ch=ch2 .cooc (ch3) 2ch = ch2
N- N-
\<»CH3 \ <»CH3
^ch(ch3)2 ^ ch (ch3) 2
0 0
t: t:
HCl HCl
,COOC(CH3)2CH=CH2 , COOC (CH3) 2CH = CH2
■HCl ■ HCl
ChT(CH ) ^0 ChT (CH) ^ 0
Eine Lösung von 164 mg 1 ,l-Dimethylallyl-o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoat (0,5 mM) in 5 ml Methylenchlorid und 5 ml absolutem Ethanol wird mit 0,5 ml 1,0 normaler Chlorwasserstoffsäure versetzt. Das Reaktionsgemisch wird unter Vakuum konzentriert, worauf man den Rückstand mit Ether behandelt, das erhaltene kristalline Produkt abfiltriert, mit A solution of 164 mg of 1, l-dimethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate (0.5 mM) in 5 ml of methylene chloride and 5 ml of absolute ethanol 0.5 ml of 1.0 normal hydrochloric acid is added. The reaction mixture is concentrated under vacuum, whereupon the residue is treated with ether and the crystalline product obtained is filtered off with
35 35
Ether wäscht und an der Luft trocknet. Auf diese Weise gelangt man zu 170 mg des im Titel angegebenen Hydrochlorids, das bei 259 bis 262° C unter Zersetzung schmilzt. Der Schmelzpunkt dieses Salzes und anderer Salze ist abhängig von der Erhitzungsgeschwindigkeit. Ether washes and air dries. In this way, 170 mg of the hydrochloride specified in the title are obtained, which melts at 259 to 262 ° C. with decomposition. The melting point of this salt and other salts depends on the rate of heating.
Beispiel 4 Example 4
o-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoesäure o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid
Na OH Oh OH
Nil • HCl Nil • HCl
Eine Lösung von 5 g 3-Isopropyl-3-methyl-5H-imidazo[2,l-a]-isoindol-2(3H) ,5-dion in 15 ml Dioxan wird unter Rühren mit einem Gemisch aus 10 ml konzentrierter Chlorwasserstoffsäure und 10 ml Wasser versetzt. Das Reaktionsgemisch wird zum Sieden erhitzt, worauf man es auf Raumtemperatur abkühlen lässt. Der dabei anfallende kristalline Feststoff wird abfiltriert, A solution of 5 g of 3-isopropyl-3-methyl-5H-imidazo [2, la] isoindole-2 (3H), 5-dione in 15 ml of dioxane is stirred with a mixture of 10 ml of concentrated hydrochloric acid and 10 ml Water added. The reaction mixture is heated to boiling, whereupon it is allowed to cool to room temperature. The resulting crystalline solid is filtered off,
u u
639 957 639 957
mit Wasser sowie Aceton gewaschen und an der Luft getrocknet. Das Filtrat wird unter Vakuum eingeengt, worauf man den hierbei erhaltenen Feststoff mit Aceton wäscht und an der Luft trocknet. Auf diese Weise erhältmaninsgesamt4,5gdes Lactonhydrochlorids der oben angegebenen Struktur A, das bei 265°C unter Zersetzung schmilzt. washed with water and acetone and air dried. The filtrate is concentrated in vacuo, whereupon the solid obtained is washed with acetone and air-dried. In this way a total of 4.5 g of the lactone hydrochloride of structure A given above is obtained, which melts at 265 ° C with decomposition.
Eine Teillösung des obigen Hydrochlorids (4,5 g) in 30 ml Wasser wird unter Rühren mit einer Lösung von 0,6 g Natriumhydroxid in 10 ml Wasser versetzt. Innerhalb weniger Minuten entsteht eine vollständige Lösung, und nach etwa 15 min scheidet sich aus der Lösung ein Feststoff ab. Dieser Feststoff wird abfiltriert. Das Filtrat wird unter Vakuum eingeengt, worauf man den erhaltenen Feststoff abfiltriert, mit dem ersten Feststoff vereinigt, mit Wasser wäscht und an der Luft trocknet. Auf diese Weise gelangt man zu 3,8 g o-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoesäure, die bei 162 bis 163° C schmilzt. A partial solution of the above hydrochloride (4.5 g) in 30 ml of water is mixed with a solution of 0.6 g of sodium hydroxide in 10 ml of water. A complete solution is formed within a few minutes and a solid separates from the solution after about 15 minutes. This solid is filtered off. The filtrate is concentrated in vacuo, whereupon the solid obtained is filtered off, combined with the first solid, washed with water and air-dried. This gives 3.8 g of o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, which melts at 162 to 163 ° C.
Eine analytisch reine Probe hat einen Schmelzpunkt von 163 bis 165°C. An analytically pure sample has a melting point of 163 to 165 ° C.
Beispiel 5 Example 5
10 10th
mical Industries) enthalten und eine solche Wirkstoffmenge aufweisen, dass sich bei Auftrag der entsprechenden wirkstoff-haltigen Dispersionen auf die jeweiligen Pflanzen mittels einer bei einem Druck von 2,8 kg/cm2 über eine vorbestimmte Zeit betriebenen Sprühdüse eine Wirkstoffmenge von etwa 0,07 bis 11,2 kg pro ha ergibt. Nach dem Besprühen werden die Pflanzen auf Treibhaustische gestellt und in üblicher Weise weiter gehegt. 2 Wochen nach erfolgter Behandlung werden die Sämlingspflanzen mit Ausnahme der Sämlingspflanzen des Windhafers, die erst nach 5 Wochen beurteilt werden, entsprechend geprüft und nach folgender Beurteilungsskala bewertet. Die hierbei erhaltenen Daten gehen aus der später folgenden Tabelle I hervor. mical Industries) and contain such an amount of active ingredient that when the corresponding active ingredient-containing dispersions are applied to the respective plants by means of a spray nozzle operated at a pressure of 2.8 kg / cm 2 for a predetermined time, an active ingredient amount of about 0.07 to 11.2 kg per ha. After spraying, the plants are placed on greenhouse tables and kept in the usual manner. 2 weeks after the treatment, the seedling plants, with the exception of the wind oat seedling plants, which are only assessed after 5 weeks, are tested accordingly and rated on the following assessment scale. The data obtained here are shown in Table I below.
15 Beurteilungsskala 15 rating scale
25 25th
20 20th
o-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoesäure o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid
Zur Herstellung des entsprechenden Natriumsalzes versetzt man eine Teillösung von 2,58 g Imidazolinylsäure in 10 ml Wasser unter Rühren mit 9,9 ml 1-normalem Natriumhydroxid. Nach 1,5 Stunden wird die Lösung unter Vakuum eingeengt und das verbleibende Wasser dann azeotrop mit Dioxan entfernt, wodurch man das hygroskopische Natriumsalz enthält, welches bei 184 bis 188° C schmilzt. To prepare the corresponding sodium salt, 9.9 ml of 1-normal sodium hydroxide are added to a partial solution of 2.58 g of imidazolinyl acid in 10 ml of water with stirring. After 1.5 hours, the solution is concentrated in vacuo and the remaining water is then removed azeotropically with dioxane, giving the hygroscopic sodium salt, which melts at 184 to 188 ° C.
Die Herstellung der entsprechenden Aminsalze erfolgt einfach j0 durch Umsetzung in Methanol. Zu diesem Zweck versetzt man eine Teillösung von 5,0 g Imidazolinylsäure in 15 ml Methanol unter Rühren mit 3,17 ml Triethylamin. Nach 0,75 Stunden ergibt sich eine klare Lösung. Die Lösung wird konzentriert und die zurückbleibende Aufschlämmung mit Hexan verdünnt, filtriert und getrocknet. Auf diese Weise gelangt man zum Triethyl-aminsalz, das bei 54 bis 55° C schmilzt. In ähnlicher Weise wird auch das Isopropylaminsalz hergestellt, das einen Schmelzpunkt von 92 bis 98° C hat. The corresponding amine salts are simply prepared by reaction in methanol. For this purpose, a partial solution of 5.0 g imidazolinyl acid in 15 ml methanol is stirred with 3.17 ml triethylamine. A clear solution is obtained after 0.75 hours. The solution is concentrated and the remaining slurry is diluted with hexane, filtered and dried. This leads to the triethylamine salt, which melts at 54 to 55 ° C. The isopropylamine salt, which has a melting point of 92 to 98 ° C., is also prepared in a similar manner.
40 40
Beispiel 6 Example 6
Wirksamkeit als Nachauflaufherbizide Die Wirksamkeit der erfindungsgemässen Verbindungen als Nachauflaufherbizide wird durch die folgenden Untersuchungen gezeigt, bei denen man eine Reihe einkeimblättriger Pflanzen, Cyperacaen und zweikeimblättriger Pflanzen mit den entsprechenden Wirkstoffen behandelt, die in Gemischen aus Wasser und Aceton dispergiert sind. Für die Untersuchungen lässt man Sämlinge der jeweiligen Pflanzen etwa 2 Wochen in getrennten Bechern wachsen. Die zu untersuchenden Wirkstoffe sind in Gemischen aus 50 Teilen Aceton und 50 Teilen Wasser dispergiert, die jeweils 0,5 % oberflächenaktives Mittel auf Basis von Polyoxyethylensorbitanmonolaurat (TWEEN 20 von Atlas Che45 Efficacy as post-emergence herbicides The efficacy of the compounds according to the invention as post-emergence herbicides is shown by the following tests, in which a number of monocotyledonous plants, cyperaceas and dicotyledonous plants are treated with the corresponding active compounds, which are dispersed in mixtures of water and acetone. For the investigations, seedlings of the respective plants are grown in separate beakers for about 2 weeks. The active compounds to be investigated are dispersed in mixtures of 50 parts of acetone and 50 parts of water, each of which contains 0.5% surface-active agent based on polyoxyethylene sorbitan monolaurate (TWEEN 20 from Atlas Che45
50 50
55 55
Prozentualer Unterschied im Wachstum gegenüber der Kontrolle* Percentage difference in growth over control *
0 - keine Wirkung 0 0 - no effect 0
1 - mögliche Wirkung 1-10 1 - possible effects 1-10
2 - leichte Wirkung 11-25 2 - light effect 11-25
3 - mittlere Wirkung 26-40 3 - medium effect 26-40
5 - eindeutige Schädigung 41-60 5 - clear injury 41-60
6 - herbizide Wirkung 61-75 6 - herbicidal activity 61-75
7 - gute herbizide Wirkung 76-90 7 - good herbicidal activity 76-90
8 - nahe vollständige Abtötung 91-99 8 - near complete kill 91-99
9 - vollständige Abtötung 100 9 - complete kill 100
35 35
4-Abnormales Wachstum, nämlich eine eindeutige physikalische Missbildung, wobei der Gesamteffekt in der Beurteilungsskala jedoch bei unter 5 liegt. 4-Abnormal growth, namely a clear physical malformation, but the overall effect on the assessment scale is less than 5.
* Bezogen auf eine visuelle Bestimmung von Stand, Grösse, Stärke, Chlorose, Wachstumsmissbildung und Gesamtaussehen der Pflanze. * Based on a visual determination of the position, size, strength, chlorosis, growth deformity and overall appearance of the plant.
Abkürzungen der Pflanzen: Abbreviations of plants:
PN - Purpurnes Cypergras (Cyperus rotundus L.) PN - Purple Cypergrass (Cyperus rotundus L.)
SE - Sesbania (Sesbania exaltata) SE - Sesbania (Sesbania exaltata)
MU - Senf (Brassica kaber) MU - Mustard (Brassica kaber)
PI - Ackerfuchsschwanz (Amaranthus retroflexus) PI - Field Foxtail (Amaranthus retroflexus)
RW - Ambrosienkraut (Ambrosia artemisiifolia) RW - Ambrosia herb (Ambrosia artemisiifolia)
MG - Purpurwinde (Ipomoea purpurea) MG - Purple Bindweed (Ipomoea purpurea)
BA - Hühnerhirse (Echinochloa crusgalli) BA - Millet (Echinochloa crusgalli)
CR - Blutfingerhirse (Digitaria sanguinalis) CR - Blood finger millet (Digitaria sanguinalis)
FO - Grüne Borstenhirse (Setaria viridis) FO - Green Bristle Millet (Setaria viridis)
WO - Windhafer (Avena fatua) WHERE - wind oat (Avena fatua)
TW - Teekraut (Sida spinosa) TW - Tea herb (Sida spinosa)
VL - Indianische Malve (Abutilon theophrasti) VL - Indian Mallow (Abutilon theophrasti)
CN - Mais (Zea mays) CN - maize (Zea mays)
CO - Baumwolle (Gossypium hirsutum) CO - Cotton (Gossypium hirsutum)
SY - Sojabohne (Glycine max) SY - Soybean (Glycine max)
RI - Reis (Oryza sativa) RI - Rice (Oryza sativa)
JW - Gewöhnlicher Stechapfel (Datura stramonium L.) JW - Common Datura (Datura stramonium L.)
Tabelle I Table I
Wirksamkeit der Verbindungen der angegebenen Formel als Vorauflaufherbizide Efficacy of the compounds of the formula given as pre-emergence herbicides
639 957 639 957
12 12
Formel Anwen- Pflanzenarten dungs-menge Formula application quantity of plants
Rj R, R3 X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI Rj R, R3 X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI
ch., ch.,
-ch(ch3)2 -ch (ch3) 2
-ch2c=ch h -ch2c = ch h
11,2 11.2
3 3rd
8 8th
8 8th
8 8th
5 5
8 8th
8 8th
9 9
7 7
7 7
6 6
9 9
- -
- -
- -
- -
4,48 4.48
7 7
9 9
9 9
9 9
5 5
9 9
9 9
9 9
3 3rd
3 3rd
8 8th
9 9
7 7
9 9
9 9
7 7
1,12 1.12
3 3rd
7 7
9 9
9 9
2 2nd
9 9
7 7
8 8th
3 3rd
3 3rd
3 3rd
6 6
7 7
9 9
9 9
5 5
0,56 0.56
1 1
3 3rd
9 9
9 9
2 2nd
8 8th
3 3rd
7 7
0 0
0 0
0 0
5 5
7 7
9 9
9 9
8 8th
0,25 0.25
3 3rd
0 0
9 9
9 9
3 3rd
7 7
5 5
6 6
5 5
- -
6 6
7 7
9 9
9 9
7 7
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch2ch2ch3 -ch2ch2ch3
h H
11,2 11.2
0 0
0 0
5 5
5 5
0 0
2 2nd
3 3rd
5 5
0 0
0 0
0 0
0 0
- -
- -
- -
- -
4,48 4.48
- -
9 9
7 7
8 8th
0 0
4 4th
2 2nd
1 1
0 0
1 1
1 1
- -
0 0
9 9
2 2nd
0 0
1,12 1.12
- -
3 3rd
3 3rd
8 8th
0 0
3 3rd
0 0
0 0
0 0
0 0
0 0
- -
0 0
8 8th
1 1
0 0
0,56 0.56
- -
0 0
1 1
6 6
0 0
2 2nd
0 0
0 0
0 0
0 0
0 0
- -
0 0
8 8th
1 1
0 0
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
/ \ / \
h H
11,2 11.2
0 0
1 1
7 7
7 7
0 0
2 2nd
5 5
7 7
0 0
4 4th
4 4th
4 4th
2 2nd
8 8th
5 5
1 1
pu —/ A pu - / A
4,48 4.48
- -
7 7
8 8th
8 8th
1 1
7 7
7 7
2 2nd
1 1
2 2nd
2 2nd
- -
0 0
9 9
3 3rd
1 1
2 \ // 2 \ //
1,12 1.12
- -
9 9
8 8th
8 8th
0 0
7 7
2 2nd
2 2nd
0 0
0 0
0 0
- -
0 0
9 9
3 3rd
0 0
\ '/ \ '/
0,56 0.56
- -
8 8th
8 8th
0 0
7 7
1 1
1 1
0 0
0 0
0 0
- -
0 0
7 7
- -
- -
0 0
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-(ch2)7ch3 - (ch2) 7ch3
h H
11,2 11.2
0 0
7 7
5 5
7 7
0 0
0 0
4 4th
4 4th
0 0
4 4th
4 4th
0 0
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
~(ch2)11ch3 ~ (ch2) 11ch3
h H
11,2 11.2
0 0
5 5
3 3rd
7 7
0 0
0 0
1 1
1 1
0 0
1 1
1 1
0 0
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch2ch=ch2 -ch2ch = ch2
h H
11,2 11.2
0 0
1 1
7 7
8 8th
0 0
2 2nd
5 5
7 7
0 0
4 4th
4 4th
4 4th
- -
- -
- -
- -
4,48 4.48
- -
3 3rd
9 9
8 8th
0 0
8 8th
8 8th
7 7
- -
0 0
5 5
- -
6 6
9 9
6 6
2 2nd
1,12 1.12
- -
2 2nd
9 9
8 8th
0 0
7 7
2 2nd
2 2nd
0 0
0 0
0 0
- -
2 2nd
8 8th
6 6
0 0
0,56 0.56
- -
0 0
8 8th
8 8th
0 0
7 7
0 0
2 2nd
0 0
0 0
0 0
- -
1 1
8 8th
6 6
0 0
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch3 -ch3
h H
11,2 11.2
1 1
8 8th
8 8th
8 8th
0 0
6 6
6 6
7 7
7 7
7 7
7 7
6 6
- -
- -
- -
- -
4,48 4.48
7 7
9 9
9 9
9 9
2 2nd
8 8th
6 6
9 9
7 7
2 2nd
8 8th
9 9
9 9
9 9
9 9
0 0
1,12 1.12
8 8th
6 6
9 9
9 9
1 1
8 8th
5 5
4 4th
3 3rd
0 0
2 2nd
9 9
8 8th
7 7
9 9
0 0
0,56 0.56
6 6
0 0
9 9
9 9
0 0
7 7
3 3rd
4 4th
0 0
0 0
0 0
9 9
9 9
7 7
9 9
0 0
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-c(ch3)ch=ch2 -c (ch3) ch = ch2
h H
1,12 1.12
8 8th
9 9
9 9
9 9
6 6
9 9
6 6
9 9
7 7
9 9
9 9
8 8th
9 9
9 9
9 9
5 5
0,56 0.56
7 7
3 3rd
9 9
9 9
7 7
9 9
7 7
9 9
7 7
6 6
7 7
9 9
9 9
9 9
9 9
3 3rd
0,28 0.28
5 5
0 0
9 9
9 9
6 6
9 9
6 6
9 9
5 5
3 3rd
8 8th
9 9
9 9
8 8th
8 8th
2 2nd
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-c(ch3)2c=ch h -c (ch3) 2c = ch h
4,48 4.48
2 2nd
0 0
9 9
9 9
4 4th
9 9
2 2nd
2 2nd
1 1
1 1
1 1
8 8th
7 7
8 8th
7 7
0 0
1,12 1.12
2 2nd
0 0
9 9
9 9
3 3rd
8 8th
1 1
2 2nd
0 0
1 1
1 1
6 6
7 7
7 7
7 7
- -
0,56 0.56
2 2nd
0 0
8 8th
9 9
2 2nd
8 8th
0 0
2 2nd
0 0
0 0
2 2nd
0 0
7 7
7 7
6 6
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch(ch3)2 -ch (ch3) 2
h H
11,2* 11.2 *
3,5 2,5 4 3.5 2.5 4
8,5 1,5 6 8.5 1.5 6
5,5 4 5.5 4
3,5 4,5 4,5 4 3.5 4.5 4.5 4
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-c(ch3)3 -c (ch3) 3
h H
11,2 11.2
0 0
0 0
0 0
9 9
0 0
4 4th
0 0
0 0
0 0
0 0
0 0
0 0
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch2ch3 -ch2ch3
h H
11,2 11.2
0 0
1 1
8 8th
8 8th
0 0
3 3rd
3 3rd
5 5
0 0
0 0
1 1
9 9
- -
- -
- -
- -
ch3 ch3
-ch2ch2ch3 -ch2ch2ch3
-c(ch3)2ch=ch2 -c (ch3) 2ch = ch2
h H
11,2 11.2
2 2nd
8 8th
3 3rd
3 3rd
0 0
0 0
0 0
0 0
0 0
0 0
0 0
0 0
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-c(ch3)2ch=ch2 -c (ch3) 2ch = ch2
h H
11,2 11.2
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
- -
- -
- -
- -
4,48 4.48
9 9
9 9
9 9
9 9
8 8th
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
HCl-Salz HCl salt
1,12 1.12
9 9
9 9
9 9
9 9
7 7
9 9
3 3rd
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
6 6
0,56 0.56
8 8th
7 7
9 9
9 9
6 6
9 9
1 1
9 9
7 7
5 5
8 8th
9 9
9 9
9 9
9 9
7 7
0,28 0.28
2 2nd
3 3rd
9 9
9 9
8 8th
9 9
1 1
5 5
3 3rd
5 5
5 5
5 5
9 9
9 9
7 7
7 7
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-c(ch3)2c=ch h -c (ch3) 2c = ch h
11,2 11.2
7 7
7 7
9 9
9 9
9 9
9 9
8 8th
9 9
8 8th
9 9
9 9
9 9
- -
- -
- -
- -
4,48 4.48
3 3rd
9 9
9 9
9 9
7 7
9 9
9 9
9 9
3 3rd
2 2nd
6 6
9 9
9 9
9 9
8 8th
6 6
HCl-Salz HCl salt
1,12 1.12
2 2nd
2 2nd
9 9
9 9
5 5
8 8th
1 1
5 5
2 2nd
0 0
5 5
6 6
9 9
8 8th
8 8th
6 6
0,56 0.56
2 2nd
2 2nd
9 9
9 9
0 0
9 9
0 0
8 8th
0 0
0 0
3 3rd
3 3rd
9 9
8 8th
8 8th
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch(ch3)c=ch h -ch (ch3) c = ch h
11,2 11.2
7 7
9 9
9 9
9 9
7 7
9 9
7 7
9 9
7 7
7 7
6 6
9 9
- -
- -
- -
- -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2-c(ci)=ch2 -ch2-c (ci) = ch2
h l'l,2 h l'l, 2nd
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
- -
- -
- -
- -
ch3 ch3
-ch(ch.,)2 -ch (ch.,) 2
-ch2ch2c=ch h -ch2ch2c = ch h
11,2 11.2
6 6
- -
4 4th
8 8th
0 0
5 5
4 4th
7 7
4 4th
4 4th
4 4th
9 9
- -
- -
- -
- -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch(ch3)ch=ch2 -ch (ch3) ch = ch2
h H
11,2 11.2
0 0
3 3rd
7 7
7 7
0 0
3 3rd
4 4th
4 4th
2 2nd
2 2nd
2 2nd
0 0
- -
- -
- -
- -
-(ch2)5— - (ch2) 5—
-c(ch3)2ch=ch2 -c (ch3) 2ch = ch2
h H
11,2 11.2
0 0
2 2nd
6 6
6 6
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
- -
- -
- -
- -
-ch(ch3)ch2ch2ch2ch2- -ch (ch3) ch2ch2ch2ch2-
-ch2c=ch h -ch2c = ch h
11,2 11.2
0 0
0 0
4 4th
0 0
0 0
4 4th
0 0
0 0
8 8th
6 6
3 3rd
5 5
- -
- -
- -
- -
ch3 ch3
—ch(ch3)2 —Ch (ch3) 2
-ch(ch3)-c(ch3)=ch2 -ch (ch3) -c (ch3) = ch2
h H
11,2 11.2
5 5
9 9
7 7
7 7
4 4th
4 4th
4 4th
4 4th
0 0
0 0
1 1
0 0
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch2ch=chch3 -ch2ch = chch3
h H
11,2 11.2
2 2nd
5 5
6 6
6 6
0 0
6 6
3 3rd
5 5
5 5
3 3rd
2 2nd
2 2nd
- -
- -
- -
- -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2c(ch3)=ch2 -ch2c (ch3) = ch2
h H
11,2 11.2
0 0
0 0
7 7
8 8th
0 0
0 0
1 1
3 3rd
0 0
0 0
0 0
0 0
- -
- -
- -
- -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2ch=c(ch3)2 -ch2ch = c (ch3) 2
h H
11,2 11.2
3 3rd
5 5
7 7
7 7
0 0
6 6
5 5
6 6
2 2nd
5 5
3 3rd
3 3rd
- -
- -
- -
- -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2 / \ -ch2 / \
h H
11,2 11.2
0 0
0 0
3 3rd
7 7
0 0
5 5
2 2nd
3 3rd
0 0
0 0
0 0
0 0
- -
- -
- -
- -
\ / \ /
» »
ch, ch,
-ch(ch,), -ch (ch,),
-ch(ch=ch,)2 -ch (ch = ch,) 2
h H
11,2 11.2
3 3rd
9 9
8 8th
9 9
4 4th
9 9
9 9
9 9
7 7
8 8th
8 8th
7 7
- -
- -
- -
- -
ch3 ch3
-ch(ch3)2 -ch (ch3) 2
-ch(ch3)-ch=chch3 -ch (ch3) -ch = chch3
h H
11,2 11.2
3 3rd
7 7
9 9
9 9
2 2nd
8 8th
7 7
9 9
6 6
5 5
7 7
5 5
- -
- -
- -
- -
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch2c(ch3)2, -ch2c (ch3) 2,
h H
11,2 11.2
5 5
0 0
6 6
9 9
0 0
7 7
5 5
4 4th
0 0
0 0
0 0
0 0
ch, ch,
ch(ch3)2 ch (ch3) 2
-ch2ch,och3 -ch2ch, och3
h H
11,2 11.2
2 2nd
0 0
9 9
9 9
7 7
0 0
6 6
8 8th
4 4th
0 0
4 4th
8 8th
8 8th
5 5
3 3rd
1 1
9 9
9 9
9 9
8 8th
8 8th
3 3rd
5 5
8 8th
8 8th
7 7
9 9
9 9
9 9
8 8th
3 3rd
7 7
7 7
5 5
5 5
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
8 8th
5 5
3 3rd
7 7
7 7
6 6
5 5
3 3rd
7 7
13 13
Anwen- Pflanzenarten dungs- Applications- plant species
menge amount
X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN
~QH)3-n ch3 ~ QH) 3-n ch3
-c-c2h5 ch3 -c-c2h5 ch3
-ch2ch2och2h5 -ch2ch2och2h5
-chj-CH=ch- v_} -chj-CH = ch- v_}
-ch2-c=c- \_y -ch2-c = c- \ _y
-CHj-c=c-ch3 -CHj-c = c-ch3
-CH- -CH-
I I.
CH CH
<3 <3
-ch2-c=c-c7hls_n -ch2-c = c-c7hls_n
-ch,cc13 -ch, cc13
-c(c2h5)2ch=ch2 -c (c2h5) 2ch = ch2
oi(cu3)2 oi (cu3) 2
fc^CH - fc ^ CH -
Cl Cl
I I.
-ch,-c=ch, -ch, -c = ch,
-ch, -ch,
2,24 2.24
0 0
0 0
5 5
6 6
7 7
0 0
0 0
0 0
1 1
6 6
1,12 1.12
0 0
0 0
5 5
3 3rd
8 8th
0 0
0 0
0 0
0 0
0 0
0,56 0.56
0 0
0 0
3 3rd
0 0
8 8th
0 0
0 0
0 0
0 0
0 0
0,28 0.28
0 0
0 0
3 3rd
0 0
0 0
0 0
0 0
0 0
0 0
0 0
h 11,2 h 11.2
8,5*8 8.5 * 8
9 9
9 9
6* 6 *
9 9
8 8th
9 9
9 9
9 9
9 9
2,24 2.24
8 8th
7 7
9 9
9 9
9 9
7 7
5 5
9 9
9 9
7 7
h 1,12 h 1.12
8 8th
8 8th
9 9
9 9
9 9
6 6
3 3rd
7 7
9 9
8 8th
0,56 0.56
7 7
3 3rd
8 8th
8 8th
9 9
3 3rd
0 0
6 6
7 7
7 7
0,28 0.28
3 3rd
2 2nd
6 6
7 7
9 9
2 2nd
0 0
0 0
2 2nd
7 7
h 11,2 h 11.2
2 2nd
0 0
3 3rd
9 9
0 0
5 5
4 4th
4 4th
0 0
0 0
0 0
1 1
11,2 11.2
6* 6 *
0 0
9 9
9 9
0 0
7 7
6 6
6 6
2 2nd
0 0
0 0
8 8th
2,24 2.24
3 3rd
0 0
3 3rd
2 2nd
9 9
0 0
0 0
0 0
0 0
h 1,12 h 1.12
2 2nd
0 0
2 2nd
0 0
0 0
0 0
0 0
0 0
0 0
h 11,2 h 11.2
0 0
0 0
7 7
9 9
0 0
4 4th
5 5
6 6
4 4th
0 0
0 0
4 4th
2,24 2.24
2 2nd
2 2nd
7 7
8 8th
9 9
2 2nd
0 0
0 0
0 0
5 5
1,12 1.12
1 1
0 0
7 7
5 5
3 3rd
0 0
0 0
0 0
0 0
2 2nd
0,56 0.56
0 0
0 0
2 2nd
2 2nd
2 2nd
0 0
0 0
0 0
0 0
0 0
h 11,2 h 11.2
4,5*7,5*7,5*8,5*2 4.5 * 7.5 * 7.5 * 8.5 * 2
5* 5 *
8,5*9 8.5 * 9
5 5
5 5
6 6
8,5 8.5
* *
2,24 2.24
8 8th
3 3rd
7 7
7 7
9 9
7 7
2 2nd
7 7
6 6
7 7
1,12 1.12
7 7
2 2nd
6 6
2 2nd
9 9
2 2nd
0 0
3 3rd
2 2nd
7 7
0,56 0.56
8 8th
2 2nd
5 5
2 2nd
7 7
0 0
0 0
0 0
0 0
6 6
h 11,2 h 11.2
4,5*4 4.5 * 4
6,5*8* 6.5 * 8 *
3* 3 *
5,5*6* 5.5 * 6 *
6,5*4 6.5 * 4
0 0
0 0
5,5 5.5
* *
h 11,2 h 11.2
4,5*6,5*8,5*9 4.5 * 6.5 * 8.5 * 9
7,5*7,5*8,5*8,5*7* 7.5 * 7.5 * 8.5 * 8.5 * 7 *
6,5*8,5*8,5 6.5 * 8.5 * 8.5
* *
2,24 2.24
7 7
3 3rd
8 8th
8 8th
9 9
2 2nd
0 0
3 3rd
8 8th
9 9
1,12 1.12
3 3rd
0 0
8 8th
5 5
9 9
0 0
0 0
0 0
2 2nd
8 8th
0,56 0.56
3 3rd
0 0
7 7
5 5
9 9
0 0
0 0
0 0
0 0
7 7
11,2 11.2
6,5*3 6.5 * 3
9 9
9 9
5 5
7,5*7 7.5 * 7
8,5*4 8.5 * 4
4 4th
7 7
8* 8th*
h 2,24 h 2.24
8 8th
0 0
6 6
0 0
8 8th
0 0
0 0
0 0
2 2nd
8 8th
1,12 1.12
7 7
0 0
6 6
0 0
0 0
0 0
0 0
0 0
0 0
7 7
0,56 0.56
5 5
0 0
5 5
0 0
0 0
0 0
0 0
0 0
0 0
7 7
h 11,2 h 11.2
3 3rd
6 6
8 8th
9 9
3 3rd
6 6
7 7
9 9
3 3rd
0 0
8 8th
5 5
2,24 2.24
0 0
0 0
6 6
2 2nd
6 6
0 0
0 0
0 0
2 2nd
3 3rd
1,12 1.12
0 0
0 0
5 5
0 0
7 7
0 0
0 0
0 0
0 0
3 3rd
0,56 0.56
0 0
0 0
3 3rd
0 0
6 6
0 0
0 0
0 0
0 0
3 3rd
h 11,2 h 11.2
2 2nd
9 9
8 8th
9 9
6 6
3 3rd
8 8th
8 8th
5 5
8 8th
8 8th
9 9
2,24 2.24
6 6
9 9
9 9
9 9
9 9
9 9
7 7
9 9
9 9
9 9
1,12 1.12
6 6
8 8th
9 9
8 8th
9 9
7 7
5 5
9 9
9 9
9 9
0,56 0.56
3 3rd
3 3rd
8 8th
5 5
8 8th
3 3rd
0 0
8 8th
9 9
9 9
0,28 0.28
2 2nd
3 3rd
7 7
3 3rd
8 8th
0 0
0 0
7 7
9 9
9 9
0,14 0.14
0 0
1 1
6 6
3 3rd
9 9
0 0
0 0
7 7
9 9
9 9
h 11,2 h 11.2
1 1
8 8th
7 7
9 9
5 5
0 0
6 6
8 8th
5 5
3 3rd
7 7
7 7
2,24 2.24
7 7
5 5
8 8th
6 6
9 9
2 2nd
2 2nd
5 5
7 7
9 9
1,12 1.12
1 1
3 3rd
7 7
3 3rd
9 9
0 0
0 0
2 2nd
6 6
9 9
0,56 0.56
1 1
0 0
8 8th
5 5
9 9
0 0
0 0
0 0
3 3rd
9 9
11,2 11.2
0 0
5 5
9 9
9 9
6 6
6 6
6 6
3 3rd
2 2nd
9 9
5 5
0 0
h 2,24 h 2.24
0 0
0 0
5 5
3 3rd
0 0
0 0
0 0
0 0
0 0
7 7
1,12 1.12
0 0
0 0
2 2nd
0 0
0 0
0 0
0 0
0 0
0 0
3 3rd
h 11,2 h 11.2
0 0
0 0
8 8th
9 9
0 0
6 6
0 0
3 3rd
0 0
0 0
0 0
0 0
4(5)11,2 4 (5) 11.2
2 2nd
7 7
9 9
9 9
8 8th
7 7
9 9
9 9
8 8th
8 8th
8 8th
9 9
ch3 2,24 ch3 2.24
0 0
8 8th
6 6
5 5
9 9
6 6
5 5
7 7
9 9
9 9
1,12 1.12
0 0
7 7
3 3rd
5 5
9 9
2 2nd
0 0
6 6
9 9
9 9
0,56 0.56
0 0
3 3rd
2 2nd
3 3rd
8 8th
0 0
0 0
1 1
9 9
7 7
0,28 0.28
0 0
3 3rd
0 0
0 0
7 7
0 0
0 0
0 0
9 9
3 3rd
4(5)11,2 4 (5) 11.2
2 2nd
7 7
9 9
3 3rd
7 7
7 7
8 8th
9 9
8 8th
2 2nd
8 8th
8 8th
ch, 2,24 ch, 2.24
0 0
2 2nd
2 2nd
3 3rd
8 8th
8 8th
0 0
0 0
2 2nd
2 2nd
1,12 1.12
0 0
0 0
0 0
2 2nd
7 7
0 0
0 0
0 0
0 0
3 3rd
SY SY
9 9
7 7
7 7
6 6
5 5
7 7
7 7
8 8th
8 8th
8 8th
7 7
9 9
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9
8 8th
9 9
7 7
8 8th
7 7
6 6
3 3rd
2 2nd
0 0
8 8th
8 8th
8 8th
8 8th
0 0
0 0
7 7
7 7
8 8th
8 8th
7 7
7 7
14 14
Anwen- Pflanzenarten dungs- Applications- plant species
menge in kg/ha PN SE MU PI RW MG TW VL BA CR FO quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO
-ch2-c=ch -ch2-c = ch
4(5)11,2 4 (5) 11.2
3 3rd
8 8th
9 9
9 9
8 8th
7 7
8 8th
9 9
8 8th
9 9
9 9
ch3 2,24 ch3 2.24
3 3rd
9 9
7 7
5 5
9 9
8 8th
6 6
8 8th
1,12 1.12
0 0
9 9
.3 .3
5 5
9 9
2 2nd
2 2nd
6 6
0,56 0.56
0 0
3 3rd
3 3rd
3 3rd
9 9
2 2nd
0 0
6 6
0,28 0.28
0 0
3 3rd
0 0
0 0
8 8th
0 0
0 0
3 3rd
0,14 0.14
0 0
2 2nd
0 0
0 0
6 6
0 0
0 0
0 0
ch(chj), ch (chj),
11,2 11.2
2 2nd
7 7
9 9
9 9
6 6
7 7
7 7
8 8th
7 7
2 2nd
7 7
1 1
2,24 2.24
3 3rd
1 1
5 5
2 2nd
2 2nd
5 5
0 0
0 0
-c-ch=chi i -c-ch = chi i
h 1,12 h 1.12
0 0
0 0
5 5
0 0
0 0
0 0
0 0
0 0
1 1
ch(ch3)2 ch (ch3) 2
-c2hs -c2hs
h 11,2 h 11.2
2 2nd
3 3rd
9 9
9 9
6 6
7 7
8 8th
9 9
6 6
0 0
7 7
2,24 2.24
7 7
3 3rd
6 6
8 8th
9 9
0 0
0 0
2 2nd
1,12 1.12
6 6
2 2nd
6 6
7 7
9 9
0 0
0 0
0 0
0,56 0.56
5 5
2 2nd
6 6
5 5
9 9
0 0
0 0
0 0
0,28 0.28
3 3rd
2 2nd
5 5
3 3rd
9 9
0 0
0 0
0 0
-ch2-c=ch -ch2-c = ch
h 11,2 h 11.2
3 3rd
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
7 7
9 9
9 9
2,24 2.24
8 8th
9 9
9 9
9 9
9 9
8 8th
7 7
9 9
1,12 1.12
8 8th
8 8th
9 9
7 7
9 9
8 8th
7 7
9 9
0,56 0.56
8 8th
8 8th
9 9
5 5
9 9
8 8th
2 2nd
9 9
0,28 0.28
7 7
7 7
9 9
5 5
9 9
6 6
2 2nd
5 5
0,14 0.14
7 7
7 7
8 8th
2 2nd
9 9
5 5
0 0
5 5
0,07 0.07
5 5
2 2nd
5 5
2 2nd
9 9
3 3rd
0 0
2 2nd
-ch,-c=ch2 -ch, -c = ch2
h 11,2 h 11.2
2 2nd
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
" 1 " 1
2,24 2.24
7 7
8 8th
9 9
9 9
9 9
7 7
3 3rd
9 9
Cl Cl
1,12 1.12
7 7
8 8th
9 9
9 9
9 9
6 6
0 0
9 9
0,56 0.56
6 6
8 8th
9 9
6 6
9 9
5 5
0 0
7 7
0,28 0.28
6 6
3 3rd
8 8th
5 5
9 9
3 3rd
0 0
5 5
0,14 0.14
5 5
0 0
8 8th
3 3rd
5 5
2 2nd
0 0
2 2nd
-ch(ch3)ch= -ch (ch3) ch =
=chch3 = chch3
4(5)11,2 4 (5) 11.2
2 2nd
8 8th
9 9
9 9
7 7
6 6
8 8th
9 9
8 8th
7 7
8 8th
ch3 2,24 ch3 2.24
6 6
7 7
3 3rd
7 7
8 8th
0 0
0 0
3 3rd
1,12 1.12
5 5
6 6
2 2nd
5 5
6 6
0 0
0 0
2 2nd
0,56 0.56
3 3rd
5 5
0 0
3 3rd
6 6
0 0
0 0
0 0
0,28 0.28
2 2nd
2 2nd
0 0
2 2nd
3 3rd
0 0
0 0
0 0
u u
1 1
3 (6) 11,2 3 (6) 11.2
1 1
0 0
8 8th
9 9
7 7
6 6
5 5
5 5
0 0
0 0
0 0
Cl Cl
X o iii u X o iii u
1 1
X u X u
1 1
3 (6)11,2 3 (6) 11.2
0 0
0 0
9 9
9 9
6 6
7 7
8 8th
9 9
0 0
0 0
0 0
Cl 2,24 Cl 2.24
0 0
0 0
5 5
3 3rd
0 0
0 0
0 0
2 2nd
1,12 1.12
0 0
0 0
5 5
2 2nd
0 0
0 0
0 0
0 0
-ch2-c=c-ch2oh h 11,2 -ch2-c = c-ch2oh h 11.2
3 3rd
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
2,24 2.24
8 8th
8 8th
9 9
9 9
9 9
9 9
5 5
9 9
1,12 1.12
7 7
6 6
9 9
6 6
9 9
6 6
3 3rd
7 7
0,56 0.56
7 7
3 3rd
8 8th
6 6
9 9
2 2nd
0 0
6 6
0,28 0.28
6 6
3 3rd
8 8th
6 6
9 9
2 2nd
0 0
3 3rd
-CH->-c=chi 1 -CH -> - c = chi 1
3 (6)11,2 3 (6) 11.2
0 0
0 0
7 7
8 8th
0 0
0 0
5 5
5 5
0 0
0 0
0 0
1 1
Cl Cl
-ch(ch3)ch= -ch (ch3) ch =
=ch-ch3 = ch-ch3
3 (6) 11,2 3 (6) 11.2
0 0
0 0
6 6
7 7
0 0
0 0
0 0
3 3rd
0 0
0 0
0 0
Cl Cl
-C2hj -C2hj
3 (6)11,2 3 (6) 11.2
0 0
0 0
7 7
9 9
5 5
4 4th
6 6
5 5
3 3rd
7 7
1 1
no, 2,24 no, 2.24
0 0
0 0
0 0
3 3rd
0 0
3 3rd
0 0
0 0
1,12 1.12
0 0
0 0
0 0
0 0
0 0
0 0
0 0
0 0
ch3 ch3
h 11,2 h 11.2
3 3rd
0 0
9 9
9 9
0 0
6 6
7 7
9 9
3 3rd
3 3rd
7 7
2,24 2.24
3 3rd
0 0
7 7
8 8th
9 9
0 0
0- 0-
0 0
1,12 1.12
2 2nd
0 0
6 6
8 8th
9 9
0 0
0 0
0 0
X u iii u !-. X u X u iii u! -. X u
1 1
h 11,2 h 11.2
3 3rd
6 6
9 9
9 9
7 7
6 6
7 7
9 9
7 7
7 7
9 9
2,24 2.24
5 5
3 3rd
7 7
8 8th
9 9
8 8th
0 0
7 7
1,12 1.12
5 5
2 2nd
7 7
7 7
9 9
6 6
0 0
7 7
0,56 0.56
3 3rd
2 2nd
5 5
7 7
9 9
5 5
0 0
7 7
0,28 0.28
2 2nd
0 0
3 3rd
6 6
8 8th
0 0
0 0
3 3rd
15 639 957 15 639 957
Formel formula
Ri Ri
R: R:
Rî Rî
X X
Anwendungs-menge in kg/ha Application quantity in kg / ha
Pflanzenarten PN SE MU PI Plant species PN SE MU PI
RW MG TW VL RW MG TW VL
BA BA
CR CR
FO FO
WOCN WOCN
CO CO
Sì Sì
chj c2h5 chj c2h5
-ch2-c=ch2 -ch2-c = ch2
h H
11,2 11.2
5 5
7 7
9 9
9 9
4 4th
4 4th
7 7
9 9
7 7
5 5
8 8th
7 7
2,24 2.24
3 3rd
0 0
8 8th
5 5
7 7
7 7
0 0
6 6
6 6
9 9
8 8th
8 8th
Cl Cl
1,12 1.12
2 2nd
0 0
7 7
5 5
6 6
5 5
0 0
2 2nd
0 0
8 8th
7 7
7 7
0,56 0.56
1 1
0 0
7 7
0 0
2 2nd
3 3rd
0 0
2 2nd
0 0
7 7
6 6
7 7
0,28 0.28
0 0
0 0
7 7
0 0
0 0
0 0
0 0
0 0
0 0
7 7
5 5
6 6
ch., ch.,
ch(ch3)2 ch (ch3) 2
-ch2-c=chc1 -ch2-c = chc1
h H
11,2 11.2
3 3rd
8 8th
9 9
9 9
9 9
7 7
8 8th
9 9
7 7
8 8th
8 8th
1 1
2,24 2.24
8 8th
9 9
9 9
9 9
9 9
8 8th
8 8th
9 9
9 9
9 9
9 9
9 9
Cl Cl
1,12 1.12
8 8th
8 8th
9 9
9 9
8 8th
8 8th
2 2nd
8 8th
9 9
9 9
9 9
9 9
0,56 0.56
8 8th
8 8th
9 9
7 7
9 9
5 5
0 0
7 7
9 9
9 9
9 9
9 9
0,28 0.28
8 8th
0 0
9 9
5 5
9 9
5 5
0 0
5 5
5 5
9 9
8 8th
9 9
ch, ch,
c2h5 c2h5
-ch(ch3)ch=chch3 -ch (ch3) ch = chch3
h H
11,2 11.2
2 2nd
2 2nd
9 9
8 8th
5 5
7 7
7 7
8 8th
7 7
5 5
6 6
7 7
2,24 2.24
3 3rd
0 0
8 8th
5 5
7 7
5 5
0 0
2 2nd
0 0
8 8th
7 7
7 7
1,12 1.12
3 3rd
0 0
6 6
2 2nd
5 5
5 5
0 0
0 0
0 0
7 7
6 6
5 5
0,56 0.56
1 1
0 0
5 5
1 1
5 5
3 3rd
0 0
0 0
0 0
7 7
7 7
3 3rd
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch-c=ch, -ch-c = ch,
3 (6)11,2 3 (6) 11.2
0 0
0 0
9 9
9 9
3 3rd
3 3rd
7 7
4 4th
2 2nd
0 0
0 0
0 0
I I.
no/2 2,24 no / 2 2.24
0 0
2 2nd
5 5
2 2nd
2 2nd
3 3rd
0 0
0 0
0 0
0 0
7 7
0 0
Cl Cl
1,12 1.12
0 0
2 2nd
0 0
0 0
0 0
0 0
0 0
0 0
0 0
0 0
3 3rd
0 0
ch3 ch3
11,2 11.2
5 5
8 8th
9 9
9 9
9 9
7 7
8 8th
9 9
7 7
9 9
8 8th
9 9
1 1
2,24 2.24
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
ch3 ch3
ch(ch3)2 ch (ch3) 2
-c-ch=ch2 -c-ch = ch2
h H
1,12 1.12
9 9
8 8th
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
1 1
0,56 0.56
9 9
8 8th
9 9
9 9
9 9
9 9
3 3rd
8 8th
9 9
9 9
9 9
9 9
ch3 ch3
0,28 0.28
8 8th
2 2nd
9 9
5 5
9 9
7 7
0 0
5 5
7 7
9 9
7 7
8 8th
0,14 0.14
3 3rd
0 0
9 9
5 5
5 5
7 7
0 0
0 0
3 3rd
8 8th
3 3rd
7 7
0,07 0.07
3 3rd
0 0
0 0
0 0
3 3rd
0 0
0 0
0 0
0 0
7 7
5 5
5 5
ch3 ch3
11,2 11.2
4 4th
4 4th
8 8th
8 8th
2 2nd
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
4 4th
1 1
2,24 2.24
9 9
0 0
9 9
7 7
9 9
9 9
3 3rd
9 9
7 7
9 9
7 7
9 9
ch3 ch3
c2h5 c2h5
-c-ch=ch2 -c-ch = ch2
1,12 1.12
9 9
0 0
9 9
7 7
9 9
9 9
2 2nd
8 8th
7 7
9 9
7 7
9 9
1 1
0,56 0.56
8 8th
0 0
9 9
3 3rd
9 9
9 9
0 0
7 7
3 3rd
9 9
7 7
8 8th
ch3 ch3
0,28 0.28
2 2nd
0 0
8 8th
3 3rd
9 9
7 7
0 0
5 5
3 3rd
7 7
3 3rd
8 8th
0,14 0.14
2 2nd
0 0
6 6
1 1
9 9
3 3rd
0 0
3 3rd
0 0
6 6
2 2nd
7 7
ch3 ch3
ch(ch3)2 ch (ch3) 2
h H
4(5)11,2 4 (5) 11.2
1 1
3 3rd
6 6
8 8th
5 5
4 4th
8 8th
9 9
4 4th
4 4th
4 4th
4 4th
Cl Cl
2,24 2.24
9 9
9 9
8 8th
8 8th
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
1,12 1.12
5 5
8 8th
9 9
8 8th
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
0,56 0.56
5 5
8 8th
8 8th
9 9
9 9
7 7
9 9
9 9
9 9
9 9
9 9
9 9
0,28 0.28
5 5
8 8th
6 6
7 7
9 9
7 7
8 8th
9 9
9 9
9 9
6 6
9 9
0,14 0.14
5 5
6 6
6 6
8 8th
9 9
6 6
6 6
8 8th
8 8th
6 6
9 9
9 9
0,07 0.07
0 0
6 6
5 5
7 7
8 8th
5 5
5 5
6 6
9 9
3 3rd
9 9
5 5
ch(ch3)2 ch (ch3) 2
11,2 11.2
0 0
6 6
9 9
9 9
3 3rd
0 0
7 7
9 9
4 4th
7 7
4 4th
7 7
1 1
2,24 2.24
6 6
2 2nd
9 9
8 8th
9 9
7 7
7 7
3 3rd
8 8th
9 9
9 9
9 9
ch3 ch3
ch(ch3)2 ch (ch3) 2
-c-c=ch h -c-c = ch h
1,12 1.12
5 5
1 1
9 9
7 7
9 9
5 5
3 3rd
3 3rd
9 9
9 9
9 9
9 9
1 1
0,56 0.56
5 5
0 0
9 9
6 6
8 8th
3 3rd
0 0
3 3rd
3 3rd
8 8th
9 9
9 9
ch(ch3)2 ch (ch3) 2
0,28 0.28
3 3rd
0 0
9 9
5 5
7 7
3 3rd
0 0
1 1
3 3rd
3 3rd
7 7
5 5
ch3 ch3
ch(ch3)2 ch (ch3) 2
-c2h5 -c2h5
4(5)11,2 4 (5) 11.2
0 0
0 0
9 9
9 9
7 7
2 2nd
7 7
7 7
4 4th
1 1
2 2nd
7 7
Cl Cl
2,24 2.24
0 0
6 6
7 7
5 5
5 5
0 0
0 0
0 0
2 2nd
0 0
7 7
5 5
1,12 1.12
0 0
1 1
6 6
1 1
3 3rd
0 0
0 0
0 0
0 0
0 0
3 3rd
3 3rd
c2h5 c2h5
ch(ch,)2 ch (ch,) 2
ch3 ch3
h H
11,2 11.2
0 0
0 0
6 6
8 8th
0 0
0 0
5 5
5 5
0 0
0 0
0 0
0 0
c;h5 c; h5
ch(ch3)2 ch (ch3) 2
-ch2-c=ch h -ch2-c = ch h
11,2 11.2
0 0
0 0
8 8th
8 8th
0 0
2 2nd
5 5
7 7
0 0
0 0
0 0
0 0
c2h5 c2h5
ch(ch3)2 ch (ch3) 2
-CHo-c=ch, 1 -CHo-c = ch, 1
h H
11,2 11.2
0 0
0 0
8 8th
8 8th
0 0
1 1
7 7
7 7
0 0
0 0
0 0
0 0
1 1
Cl Cl
ch, ch,
ch(ch,)2 ch (ch,) 2
-ch2-c=ch -ch2-c = ch
4 (5)11,2 4 (5) 11.2
0 0
0 0
7 7
8 8th
3 3rd
0 0
5 5
5 5
4 4th
1 1
4 4th
4 4th
Cl Cl
ch3 ch3
ch(ch,)2 ch (ch,) 2
-ch(ch3)ch=chch, -ch (ch3) ch = chch,
4(5)11,2 4 (5) 11.2
2 2nd
6 6
8 8th
8 8th
4 4th
4 4th
7 7
9 9
7 7
4 4th
4 4th
4 4th
Cl Cl
2,24 2.24
3 3rd
2 2nd
9 9
5 5
8 8th
5 5
0 0
2 2nd
7 7
6 6
6 6
7 7
1,12 1.12
3 3rd
2 2nd
6 6
6 6
6 6
5 5
0 0
2 2nd
2 2nd
5 5
5 5
7 7
0,56 0.56
3 3rd
7 7
6 6
5 5
5 5
5 5
0 0
0 0
0 0
0 0
5 5
5 5
ch3 ch3
c2h5 c2h5
h h h h
11,2 11.2
3 3rd
8 8th
8 8th
8 8th
0 0
5 5
7 7
9 9
7 7
4 4th
7 7
7 7
ch, ch,
ch(ch3)2 ch (ch3) 2
h h h h
11,2 11.2
2 2nd
3 3rd
7 7
8 8th
1 1
5 5
7 7
8 8th
6 6
2 2nd
4 4th
4 4th
2,24 2.24
5 5
2 2nd
9 9
8 8th
9 9
7 7
7 7
7 7
9 9
8 8th
8 8th
8 8th
1,12 1.12
3 3rd
2 2nd
9 9
8 8th
9 9
7 7
5 5
7 7
8 8th
9 9
8 8th
6 6
0,56 0.56
3 3rd
0 0
9 9
3 3rd
9 9
6 6
0 0
5 5
6 6
8 8th
7 7
5 5
639 957 639 957
16 16
Formel formula
Anwen- Pflanzenarten dungs- Applications- plant species
menge amount
X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI
CH, CH(CH,)2 CH, CH (CH,) 2
CH3 CH(CH3)2 CH3 CH (CH3) 2
CH3 CH(CH3)2 CH3 CH (CH3) 2
CH3 CH(CH3)2 CH3 CH (CH3) 2
H H
-CH2-C=CH2 CI -CH2-C = CH2 CI
CH=CHt CH = CHt
I I.
-CH-C=CH CH3 -CH-C = CH CH3
I I.
-c-ch=ch2 ch3 -c-ch = ch2 ch3
3 (6)11,2 3 7976786247 Cl 3 (6) 11.2 3 7976786247 Cl
4 (5)11,2 278977786575 Cl 4 (5) 11.2 278977786575 Cl
H 11,2 7 H 11.2 7
9 6 8 7 9 7 9 6 8 7 9 7
4(5)11,2 478766697379 Cl 4 (5) 11.2 478766697379 Cl
* Mittelwert aus zwei oder mehr Versuchen Beispiel 7 * Average of two or more attempts Example 7
Wirksamkeit als Vorauflaufherbizide Die Wirksamkeit der erfindungsgemässen Verbindungen als Vorauflaufherbizide wird durch folgende Untersuchungen gezeigt, für die man Samen oder Fortpflanzungsorgane verschiedener einkeimblättriger Pflanzen, Cyperacaen und zweikeimblätt-riger Pflanzen getrennt mit Pflanzenerde vermischt und das so erhaltene Gemisch dann auf eine etwa 2,5 cm hohe Erdschicht in getrennte Becher einbringt. Nach dem Pflanzen besprüht man Efficacy as pre-emergence herbicides The efficacy of the compounds according to the invention as pre-emergence herbicides is shown by the following tests, for which seeds or reproductive organs of various monocotyledonous plants, cyperaceans and dicotyledonous plants are mixed separately with potting soil and the mixture thus obtained is then raised to an approximately 2.5 cm high Place the soil layer in separate cups. After planting you spray
25 25th
30 30th
die Becher in solcher Menge mit der jeweiligen Lösung des Wirkstoffs in Gemischen aus Wasser und Aceton, das sich pro Becher eine Wirkstoffmenge von etwa 0,28 bis 11,2 kg pro ha ergibt. Die behandelten Becher werden dann auf Treibhaustische gestellt, bewässert und in üblicher Weise weiter gehegt. Drei oder vier Wochen nach erfolgter Behandlung werden die Untersuchungen abgebrochen, wobei man jeden Becher entsprechend prüft und nach der in Beispiel 6 angegebenen Beurteilungsskala bewertet. Die hierbei erhaltenen Daten gehen aus der folgenden Tabelle II hervor. the cups in such an amount with the respective solution of the active ingredient in mixtures of water and acetone that results in an amount of active ingredient per cup of about 0.28 to 11.2 kg per ha. The treated cups are then placed on hothouse tables, watered and kept in the usual way. The investigations are stopped three or four weeks after the treatment has been carried out, each cup being checked accordingly and rated on the evaluation scale given in Example 6. The data obtained here are shown in Table II below.
Tabelle II Table II
Wirksamkeit der Verbindungen der angegebenen Formel als Vorauflaufherbizide Efficacy of the compounds of the formula given as pre-emergence herbicides
.COOH. .COOH.
x- x-
Formel formula
R, R-, R, R-,
Anwen- Pflanzenarten dungs- Applications- plant species
menge in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW
ch, ch,
ch(ch3)2 ch (ch3) 2
-ch2-c=ch h -ch2-c = ch h
11,2 11.2
9 9
8 8 8 8
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
8 8th
4,48 4.48
9 9
9 9 9 9
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9 9 9 9 9
9 9
9 - 9 -
1,12* 1.12 *
9 9
7,5 9 7.5 9
9 9
5 5
8 8th
8,5 8.5
8,5 9 8.5 9
9 9
9 9
9 8,5 9 9 8.5 9
8 8th
9 - 9 -
0,56* 0.56 *
9 9
6,5 9 6.5 9
9 9
3 3rd
8 8th
7,5 7.5
8,5 7,5 7 8.5 7.5 7
9 9
8,5 7,5 8 8.5 7.5 8
8 8th
8,5 - 8.5 -
0,28 0.28
8 8th
0 9 0 9
9 9
3 3rd
7 7
5 5
6 6
5 5
- -
6 6
7 9 9 7 9 9
7 7
- - - -
0,07 0.07
9 9
0 8 0 8
9 9
0 0
7 7
5 5
6 6
6 6
7 7
7 7
7 5 8 7 5 8
7 7
6 - 6 -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2ch2ch3 -ch2ch2ch3
h H
11,2 11.2
9 9
8 9 8 9
9 9
9 9
8 8th
8 8th
8 8th
7 7
8 8th
9 9
8 8th
4,48 4.48
6 6
8 8 8 8
9 9
2 2nd
8 8th
8 8th
8 8th
6 6
7 7
8 8th
8 7 9 8 7 9
8 8th
6 - 6 -
1,12 1.12
3 3rd
7 8 7 8
9 9
0 0
7 7
7 7
2 2nd
0 0
0 0
0 0
7 3 8 7 3 8
5 5
0 - 0 -
0,56 0.56
2 2nd
7 7 7 7
9 9
0 0
4 4th
5 5
1 1
0 0
0 0
0 0
4 1 7 4 1 7
1 1
0 - 0 -
ch, ch,
-ch(ch3)2 -ch (ch3) 2
-ch2 -ch2
h H
11,2 11.2
9 9
8 9 8 9
9 9
8 8th
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
4,48 4.48
9 9
8 9 8 9
9 9
5 5
8 8th
9 9
8 8th
8 8th
8 8th
9 9
7 3 9 7 3 9
8 8th
9 - 9 -
1,12 1.12
8 8th
5 8 5 8
9 9
0 0
7 7
7 7
7 7
5 5
7 7
7 7
2 2 7 2 2 7
3 3rd
7 - 7 -
0,56 0.56
1 1
0 8 0 8
9 9
0 0
7 7
5 5
5 5
0 0
2 2nd
3 3rd
0 1 1 0 1 1
0 0
3 - 3 -
ch, ch,
-entent -entent
-(ch2)7ch3 - (ch2) 7ch3
h H
11,2 11.2
9 9
3 9 3 9
9 9
8 8th
7 7
8 8th
7 7
9 9
9 9
9 9
4 4th
4,48 4.48
9 9
9 8 9 8
9 9
0 0
7 7
7 7
6 6
7 7
8 8th
9 9
5 5 6 5 5 6
6 6
8 - 8th -
1,12 1.12
9 9
0 9 0 9
9 9
- -
7 7
2 2nd
3 3rd
5 5
5 5
8 8th
2 2 2 2 2 2
3 3rd
7 - 7 -
0,56 0.56
8 8th
0 8 0 8
9 9
0 0
7 7
0 0
2 2nd
0 0
2 2nd
7 7
0 2 0 0 2 0
3 3rd
3 - 3 -
17 17th
639 957 639 957
Formel formula
R? R?
Anwen- Pflanzenarten dungs- Applications- plant species
menge in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW
CH -CH(CH3)2 CH -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CHj -CH(CH3)2 CHj -CH (CH3) 2
ch3 -CH(CH3), ch3 -CH (CH3),
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
ch3 -ch2ch2ch3 ch3 -ch2ch2ch3
CH3 -encens), CH3 -encens),
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 -(CH2)- CH3 -CH (CH3) 2 - (CH2) -
-CH(CH3)CH2CH2CH2CH2- -CH (CH3) CH2CH2CH2CH2-
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH, -entent, CH, -entent,
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH, -CH(CH3)2 CH, -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH3 -CH(CH3)2 CH3 -CH (CH3) 2
CH, -CH(CH3)2 CH, -CH (CH3) 2
CH, -CH(CH3)2 CH, -CH (CH3) 2
-(ch3)nch3 - (ch3) nch3
-ch2ch=ch2 -ch2ch = ch2
-c<ch3)2ch=ch2 -c <ch3) 2ch = ch2
-c(ch3)2c=ch -c (ch3) 2c = ch
-ch(ch3)2 -c(ch3)3 -ch (ch3) 2 -c (ch3) 3
-ch2ch3 -ch2ch3
-c(ch3)2ch=ch2 -ch(ch3)c=ch -c (ch3) 2ch = ch2 -ch (ch3) c = ch
-ch2c(c1)=ch2 -ch2c (c1) = ch2
-ch2ch2c=ch -ch2ch2c = ch
-ch(ch3)chch2 -ch (ch3) chch2
-c(ch3)2ch=ch2 -ch,c-ch -c (ch3) 2ch = ch2 -ch, c-ch
-ch2ch=chch3 -ch,c(ch3)=ch2 -ch2ch=c(ch3)2 -ch2ch = chch3 -ch, c (ch3) = ch2 -ch2ch = c (ch3) 2
H H
11,2 11.2
9 9
3 3rd
8 8th
9 9
0 0
7 7
7 7
8 8th
8 8th
9 9
9 9
4 4th
4,48 4.48
9 9
5 5
8 8th
9 9
0 0
7 7
7 7
7 7
7 7
8 8th
9 9
4 4th
1,12 1.12
9 9
0 0
8 8th
9 9
0 0
6 6
3 3rd
6 6
3 3rd
6 6
8 8th
2 2nd
0,56 0.56
6 6
0 0
7 7
9 9
0 0
2 2nd
0 0
2 2nd
2 2nd
2 2nd
7 7
0 0
H H
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
9 9
9 9
8 8th
9 9
9 9
8 8th
4,48 4.48
9 9
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
9 9
9 9
9 9
9 9
8 8th
1,12 1.12
9 9
7 7
8 8th
9 9
0 0
8 8th
7 7
7 7
7 7
7 7
8 8th
7 7
0,56 0.56
9 9
0 0
8 8th
9 9
0 0
8 8th
2 2nd
6 6
5 5
5 5
7 7
7 7
H H
11,2 11.2
9 9
9 9
9 9
9 9
7 7
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
4,48 4.48
9 9
9 9
9 9
9 9
7 7
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
1,12* 1.12 *
7,6 3,5 9 7.6 3.5 9
9 9
2 2nd
7,6 5 7.6 5
8 8th
7,5 4,5 7 7.5 4.5 7
8,6 8.6
0,56* 0.56 *
5,6 0 5.6 0
9 9
9 9
0 0
7,3 3,5 6,7 5,5 1 7.3 3.5 6.7 5.5 1
5 5
8,3 8.3
0,28 0.28
3 3rd
0 0
8 8th
8 8th
0 0
7 7
0 0
1 1
2 2nd
0 0
2 2nd
8 8th
H H
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
9 9
9 9
8 8th
4,48 4.48
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
1,12 1.12
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
9 9
9 9
7 7
0,56 0.56
9 9
6 6
9 9
9 9
5 5
7 7
7 7
8 8th
7 7
8 8th
8 8th
6 6
0,07 0.07
9 9
0 0
8 8th
8 8th
0 0
7 7
2 2nd
5 5
0 0
2 2nd
6 6
0 0
H H
11,2 11.2
9 9
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
8 8th
8 8th
9 9
9 9
8 8th
0,56 0.56
8 8th
0 0
8 8th
9 9
0 0
8 8th
5 5
6 6
6 6
6 6
7 7
7 7
H H
11,2 11.2
7 7
5 5
8 8th
9 9
3 3rd
8 8th
8 8th
8 8th
7 7
9 9
9 9
8 8th
11,2 11.2
9 9
5 5
8 8th
9 9
7 7
8 8th
9 9
9 9
6 6
7 7
8 8th
7 7
0,06 0.06
0 0
0 0
2 2nd
9 9
0 0
0 0
0 0
0 0
0 0
0 0
0 0
7 7
H H
11,2 11.2
9 9
8 8th
8 8th
9 9
7 7
8 8th
9 9
9 9
7 7
7 7
7 7
9 9
1,12 1.12
9 9
5 5
8 8th
9 9
1 1
6 6
2 2nd
5 5
0 0
2 2nd
5 5
1 1
H H
11,2 11.2
0 0
0 0
8 8th
6 6
0 0
4 4th
6 6
6 6
0 0
0 0
0 0
0 0
H H
11,2 11.2
9 9
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
0,56 0.56
9 9
- -
- -
- -
3 3rd
8 8th
9 9
8 8th
7 7
7 7
8 8th
8 8th
H H
11,2 11.2
9 9
9 9
9 9
9 9
8 8th
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
0,14 0.14
8 8th
- -
- -
- -
0 0
8 8th
9 9
7 7
7 7
7 7
8 8th
8 8th
H H
11,2 11.2
9 9
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
2,24 2.24
9 9
- -
- -
- -
2 2nd
8 8th
8 8th
7 7
7 7
6 6
8 8th
8 8th
H H
11,2 11.2
9 9
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
7 7
8 8th
7 7
1,12 1.12
9 9
- -
- -
- -
0 0
8 8th
9 9
8 8th
7 7
7 7
8 8th
7 7
H H
11,2 11.2
9 9
0 0
8 8th
9 9
0 0
7 7
9 9
6 6
6 6
6 6
6 6
7 7
H H
11,2 11.2
9 9
9 9
9 9
9 9
7 7
9 9
5 5
9 9
9 9
9 9
9 9
9 9
0,56 0.56
6 6
- -
- -
- -
0 0
2 2nd
0 0
0 0
9 9
9 9
9 9
9 9
0,14 0.14
0 0
- -
- -
- -
0 0
0 0
0 0
0 0
8 8th
9 9
7 7
0 0
H H
11,2 11.2
9 9
9 9
9 9
9 9
8 8th
8 8th
9 9
9 9
8 8th
9 9
9 9
7 7
2,24 2.24
9 9
- -
- -
- -
1 1
8 8th
8 8th
8 8th
7 7
6 6
8 8th
7 7
H H
11,2 11.2
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
9 9
9 9
8 8th
2,24 2.24
9 9
- -
- -
- -
2 2nd
8 8th
8 8th
8 8th
7 7
7 7
8 8th
8 8th
H H
11,2 11.2
9 9
9 9
9 9
8 8th
8 8th
9 9
9 9
9 9
8 8th
8 8th
9 9
8 8th
0,56 0.56
8 8th
- -
- -
- -
0 0
8 8th
9 9
7 7
6 6
7 7
7 7
2 2nd
H H
11,2 11.2
9 9
9 9
9 9
9 9
8 8th
8 8th
9 9
8 8th
9 9
9 9
9 9
8 8th
0,28 0.28
9 9
- -
- -
- -
0 0
7 7
9 9
8 8th
8 8th
9 9
9 9
7 7
H H
11,2 11.2
3 3rd
8 8th
8 8th
8 8th
0 0
7 7
8 8th
8 8th
7 7
8 8th
9 9
0 0
2,28 2.28
8 8th
- -
- -
- -
0 0
9 9
9 9
6 6
3 3rd
5 5
5 5
0 0
H H
11,2 11.2
9 9
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
9 9
9 9
9 9
8 8th
1,12 1.12
9 9
- -
- -
- -
0 0
8 8th
8 8th
8 8th
7 7
7 7
9 9
3 3rd
0,25 0.25
9 9
- -
- -
- -
0 0
7 7
7 7
6 6
7 7
6 6
7 7
0 0
0,07 0.07
7 7
- -
- -
- -
0 0
2 2nd
0 0
0 0
0 0
3 3rd
2 2nd
0 0
H H
11,2 11.2
9 9
9 9
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
9 9
9 9
9 9
8 8th
0,56 0.56
9 9
0 0
- -
- -
0 0
7 7
7 7
8 8th
7 7
7 7
9 9
6 6
H H
11,2 11.2
8 8th
8 8th
8 8th
8 8th
0 0
8 8th
8 8th
8 8th
7 7
8 8th
8 8th
5 5
2,24 2.24
9 9
- -
- -
- -
0 0
7 7
8 8th
6 6
6 6
6 6
7 7
2 2nd
9 9 9 -8 8 7 - 9 9 9 -8 8 7 -
9 9 9 9 -9 8 9 9 -9 7 8 9 - 9 9 9 9 -9 8 9 9 -9 7 8 9 -
7 9 9 7 9 9
12 7-7 12 7-7
7 8 5 7 8 5
0 0 0 0 0 0 0 0
8 6 8 6
8 9 8 8 9 8
3-9 3-9
9 8 9 9 8 9
13 5-9 13 5-9
2 8 5 - 2 8 5 -
3 8 9 3 8 9
639 957 639 957
18 18th
Formel Anwen- Pflanzenarten dungs-menge r1 r, r3 X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW Formula application- plant species quantity r1 r, r3 X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW
ch3 ch3
-CH(CHj)2 -CH (CHj) 2
-C(CHj)2CH=CH2 -C (CHj) 2CH = CH2
H H
11,2 11.2
9 9
9 9
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
9 9
9 9
9 9
HCl-Salz HCl salt
1,12 1.12
9 9
6 6
8 8th
9 9
3 3rd
8 8th
7 7
8 8th
6 6
7 7
9 9
8 8th
8 8th
9 9
8 8th
9 - 9 -
0,56 0.56
9 9
0 0
8 8th
9 9
0 0
8 8th
7 7
7 7
3 3rd
8 8th
9 9
9 9
7 7
8 8th
7 7
9 - 9 -
0,14 0.14
9 9
0 0
8 8th
9 9
0 0
3 3rd
0 0
5 5
3 3rd
5 5
7 7
0 0
1 1
6 6
7 7
9 - 9 -
CHj CHj
-CH(CHj)2 -CH (CHj) 2
-C(CHj)2C=CH -C (CHj) 2C = CH
h H
11,2 11.2
9 9
8 8th
8 8th
9 9
6 6
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
HCl-Salz HCl salt
1,12 1.12
9 9
0 0
8 8th
9 9
1 1
8 8th
6 6
7 7
8 8th
8 8th
8 8th
8 8th
7 7
8 8th
7 7
8 - 8th -
0,56 0.56
8 8th
0 0
8 8th
9 9
0 0
8 8th
0 0
3 3rd
7 7
7 7
3 3rd
7 7
3 3rd
8 8th
6 6
7 - 7 -
0,14 0.14
2 2nd
0 0
8 8th
9 9
0 0
7 7
0 0
1 1
2 2nd
0 0
2 2nd
1 1
0 0
7 7
1 1
1 - 1 -
CHj CHj
CH(CHj)2 CH (CHj) 2
-CH2C(CH3)j -CH2C (CH3) j
H H
11,2 11.2
8 8th
0 0
8 8th
9 9
3 3rd
8 8th
9 9
8 8th
3 3rd
3 3rd
5 5
6 6
2,24 2.24
2 2nd
0 0
7 7
7 7
5 5
0 0
0 0
0 0
2 2nd
1 1
7 7
2 2nd
7 7
1,12 1.12
0 0
0 0
0 0
5 5
1 1
0 0
0 0
0 0
2 2nd
0 0
7 7
0 0
7 7
CHj CHj
CH(CHj)2 CH (CHj) 2
-ch2ch2och3 -ch2ch2och3
h H
11,2 11.2
9 9
7 7
9 9
9 9
3 3rd
8 8th
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
2,24 2.24
5 5
0 0
8 8th
7 7
3 3rd
0 0
0 0
0 0
6 6
2 2nd
7 7
6 6
9 9
fî~\ fî ~ \
1,12 1.12
5 5
0 0
2 2nd
0 0
1 1
0 0
0 0
0 0
2 2nd
1 1
1 1
2 2nd
7 7
CHj CHj
CH(CHj)2 CH (CHj) 2
H H
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
2,24 2.24
9 9
8 8th
8 8th
9 9
8 8th
9 9
9 9
9 9
8 8th
9 9
8 8th
8 8th
9 9
1,12 1.12
9 9
8 8th
8 8th
7 7
8 8th
7 7
8 8th
9 9
8 8th
8 8th
7 7
8 8th
9 9
0,56 0.56
9 9
2 2nd
8 8th
7 7
8 8th
3 3rd
7 7
9 9
7 7
8 8th
7 7
8 8th
8 8th
0,28 0.28
9 9
0 0
7 7
7 7
7 7
1 1
0 0
9 9
3 3rd
5 5
5 5
7 7
9 9
ch2 ch2
CH(CHj)2 CH (CHj) 2
-QH13-n h -QH13-n h
11,2 11.2
9 9
8 8th
9 9
9 9
7 7
8 8th
8 8th
8 8th
8 8th
8 8th
9 9
7 7
2,24 2.24
9 9
2 2nd
2 2nd
9 9
6 6
2 2nd
3 3rd
9 9
2 2nd
2 2nd
8 8th
6 6
9 9
1,12 1.12
9 9
0 0
0 0
3 3rd
5 5
0 0
0 0
0 0
1 1
1 1
2 2nd
2 2nd
7 7
CHj CHj
H H
11,2 11.2
9 9
8 8th
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
1 1
2,24 2.24
9 9
0 0
8 8th
9 9
8 8th
2 2nd
3 3rd
3 3rd
2 2nd
3 3rd
8 8th
7 7
9 9
CHj CHj
CH(CHj)2 CH (CHj) 2
-c-c2hs -c-c2hs
1 1
1,12 1.12
9 9
0 0
5 5
9 9
3 3rd
0 0
0 0
0 0
0 0
2 2nd
5 5
3 3rd
9 9
CHj CHj
CHj CHj
CH(CHj)2 CH (CHj) 2
-chjchjoqhj -chjchjoqhj
H H
11,2 11.2
9 9
8 8th
8 8th
9 9
5 5
8 8th
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
2,24 2.24
9 9
0 0
2 2nd
1 1
5 5
0 0
0 0
2 2nd
5 5
6 6
5 5
6 6
8 8th
1,12 1.12
2 2nd
0 0
1 1
0 0
3 3rd
Q Q
0 0
0 0
1 1
0 0
0 0
4 4th
6 6
CHj CHj
CH(CHj)2 CH (CHj) 2
-CH2CH=CH-C6H5 -CH2CH = CH-C6H5
h H
11,2 11.2
9 9
9 9
9 9
9 9
7 7
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
2,24 2.24
8 8th
0 0
6 6
6 6
7 7
1 1
1 1
9 9
6 6
3 3rd
8 8th
5 5
8 8th
1,12 1.12
6 6
0 0
3 3rd
3 3rd
0 0
0 0
0 0
0 0
0 0
0 0
3 3rd
CHj CHj
CH(CHj)2 CH (CHj) 2
-CH2-C=C-C6Hs h -CH2-C = C-C6Hs h
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9
9 9
9 9
7 7
2,24 2.24
9 9
3 3rd
8 8th
7 7
6 6
6 6
6 6
9 9
3 3rd
5 5
2 2nd
3 3rd
8 8th
1,12 1.12
8 8th
0 0
2 2nd
2 2nd
3 3rd
2 2nd
0 0
5 5
2 2nd
0 0
0 0
0 0
2 2nd
CHj CHj
CH(CHj)2 CH (CHj) 2
-ch2-c=c-ch3 -ch2-c = c-ch3
H H
11,2 11.2
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
9 9
8 8th
2,24 2.24
9 9
7 7
8 8th
9 9
9 9
6 6
8 8th
9 9
9 9
8 8th
8 8th
7 7
9 9
1,12 1.12
9 9
2 2nd
9 9
9 9
9 9
5 5
3 3rd
8 8th
8 8th
8 8th
7 7
7 7
9 9
0,56 0.56
9 9
0 0
3 3rd
9 9
9 9
2 2nd
0 0
7 7
2 2nd
8 8th
7 7
7 7
8 8th
0,28 0.28
6 6
0 0
5 5
7 7
3 3rd
0 0
0 0
0 0
0 0
3 3rd
7 7
5 5
7 7
CHj CHj
CH(CHj)2 CH (CHj) 2
-çh-<1 -çh- <1
H H
11,2 11.2
9 9
8 8th
9 9
9 9
9 9
8 8th
9 9
9 9
9 9
9 9
9 9
9 9
CH-, CH-,
2,24 2.24
9 9
5 5
8 8th
8 8th
9 9
7 7
7 7
9 9
8 8th
9 9
8 8th
8 8th
8 8th
3 3rd
1,12 1.12
9 9
0 0
6 6
- 7 - 7th
7 7
0 0
0 0
7 7
3 3rd
7 7
7 7
6 6
8 8th
0,56 0.56
9 9
0 0
3 3rd
5 5
2 2nd
0 0
0 0
0 0
0 0
1 1
7 7
5 5
2 2nd
CHj CHj
CH(CHj)2 CH (CHj) 2
-CH2-C=C-C7H15-n -CH2-C = C-C7H15-n
H H
11,2 11.2
9 9
1 1
8 8th
9 9
3 3rd
8 8th
8 8th
8 8th
8 8th
9 9
9 9
7 7
2,24 2.24
9 9
0 0
6 6
6 6
9 9
2 2nd
0 0
8 8th
9 9
5 5
5 5
6 6
7 7
1,12 1.12
9 9
0 0
3 3rd
2 2nd
7 7
0 0
0 0
7 7
5 5
2 2nd
2 2nd
5 5
7 7
0,56 0.56
0 0
0 0
2 2nd
0 0
3 3rd
0 0
0 0
0 0
2 2nd
1 1
1 1
3 3rd
3 3rd
CHj CHj
CH(CHj)2 CH (CHj) 2
-ch2cci3 -ch2cci3
H H
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
9 9
8 8th
2,24 2.24
9 9
7 7
8 8th
9 9
9 9
8 8th
6 6
9 9
9 9
8 8th
8 8th
8 8th
8 8th
1,12 1.12
9 9
3 3rd
8 8th
5 5
9 9
5 5
2 2nd
8 8th
8 8th
8 8th
7 7
8 8th
7 7
0,56 0.56
9 9
0 0
7 7
5 5
7 7
3 3rd
0 0
7 7
7 7
7 7
7 7
7 7
6 6
0,28 0.28
9 9
0 0
6 6
5 5
2 2nd
3 3rd
0 0
5 5
5 5
3 3rd
7 7
6 6
3 3rd
CHj CHj
CH(CHj), CH (CHj),
-C(C2Hs)2CH=CH, -C (C2Hs) 2CH = CH,
H H
11,2 11.2
9 9
9 9
8 8th
9 9
8 8th
9 9
9 9
9 9
9 9
8 8th
9 9
8 8th
2,24 2.24
9 9
5 5
8 8th
9 9
9 9
7 7
3 3rd
7 7
9 9
9 9
8 8th
8 8th
9 9
1,12 1.12
9 9
3 3rd
8 8th
5 5
7 7
5 5
0 0
7 7
9 9
8 8th
7 7
7 7
8 8th
0,56 0.56
9 9
0 0
7 7
0 0
6 6
0 0
0 0
3 3rd
5 5
7 7
7 7
7 7
6 6
19 19th
639 957 639 957
Formel formula
R, R, R, R,
Anwen- Pflanzenarten dungs- Applications- plant species
menge amount
X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW
CH3 CH(CH3)2 CH3 CH (CH3) 2
ch(ch3)2 ch (ch3) 2
H 11,2 0 0 H 11.2 0 0
04000030 04000030
CHj CHj
CH(CHj)2 CH (CHj) 2
iO OK
H 11,2 H 11.2
0 0
0 0
8 8th
9 9
0 0
7 7
6 6
7 7
3 5 3 5
6 3 6 3
j\ / j \ /
c=ch c = ch
CH, CH,
CH(CHj)2 CH (CHj) 2
-ch2-c=ch2 -ch2-c = ch2
4(5)11,2 4 (5) 11.2
9 9
7 7
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9 9 9
9 8 9 8
1 1
CHj 2,24 CHj 2.24
9 9
8 8th
8 8th
8 8th
8 8th
8 8 8 8
9 9 9 9
6 6
7 7
7 7
8 8th
Cl Cl
1,12 1.12
7 7
7 7
5 5
7 7
7 7
8 5 8 5
8 9 8 9
1 1
5 5
6 6
8 8th
0,56 0.56
5 5
5 5
2 2nd
7 7
5 5
0 0 0 0
0 8 0 8
0 0
3 3rd
3 3rd
7 7
CHj CHj
CH(CHj)2 CH (CHj) 2
-CH3 -CH3
4(5)11,2 4 (5) 11.2
9 9
8 8th
9 9
9 9
8 8th
7 7
8 8th
9 9
9 8 9 8
8 8 8 8
CH3 2,24 CH3 2.24
8* 8th*
8 8th
7 7
4* 4 *
7,5*7 7.5 * 7
7 7
8* 4* 8 * 4 *
5,5*9* 5.5 * 9 *
8 8th
5 5
7 7
7 7
1,12 1.12
6* 6 *
8 8th
2 2nd
3,5*3* 3.5 * 3 *
7 7
6 6
5,5*0* 5.5 * 0 *
4,5*9* 4.5 * 9 *
2 2nd
2 2nd
7 7
7 7
0,56 0.56
3,5 3.5
* *
8 8th
0 0
0* 0 *
1* 1*
3,5*0* 3.5 * 0 *
0,5*9* 0.5 * 9 *
CHj CHj
CH(CHj)2 CH (CHj) 2
-ch2-c=ch -ch2-c = ch
4(5)11,2 4 (5) 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9 9 9
9 8 9 8
CH3 2,24 CH3 2.24
9 9
8 8th
8 8th
8 8th
8 8th
8 7 8 7
9 9 9 9
9 9
1,12 1.12
9 9
8 8th
5 5
7 7
8 8th
6 3 6 3
7 9 7 9
8 8th
0,56 0.56
6 6
8 8th
2 2nd
6 6
7 7
3 0 3 0
2 9 2 9
8 8th
CH(CH3), CH (CH3),
H 11,2 H 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9 9 9
9 8 9 8
1 1
2,24 2.24
9 9
0 0
7 7
6 6
9 9
8 0 8 0
5 8 5 8
7 7
7 7
7 7
8 8th
CHj CHj
CH(CH3)2 CH (CH3) 2
-c-ch=ch2 -c-ch = ch2
1 1
1,12 1.12
9 9
0 0
5 5
5 5
6 6
3 0 3 0
2 2 2 2
6 6
6 6
6 6
8 8th
CH(CHj)2 CH (CHj) 2
CH, CH,
CH(CHj)2 CH (CHj) 2
-CA -CA
H 11,2 H 11.2
8 8th
6 6
8 8th
9 9
8 8th
8 8th
8 8th
9 9
7 6 7 6
8 8 8 8
(+)-Isomer (+) - isomer
1,12 1.12
8 8th
5 5
8 8th
8 8th
9 9
5 0 5 0
0 8 0 8
9 9
8 8th
8 8th
9 9
0,56 0.56
7 7
5 5
7 7
7 7
9 9
2 0 2 0
0 8 0 8
8 8th
8 8th
7 7
9 9
0,28 0.28
7 7
3 3rd
7 7
5 5
9 9
2 0 2 0
0 8 0 8
7 7
7 7
7 7
7 7
CHj CHj
CH(CH3)2 CH (CH3) 2
-ch2-c=ch -ch2-c = ch
H 11,2 H 11.2
9 9
9 9
9 9
9 9
8 8th
8 8th
8 8th
8 8th
9 9 9 9
9 8 9 8
(-)-Isomer (-)-Isomer
1,12 1.12
9 9
8 8th
8 8th
8 8th
9 9
8 7 8 7
9 9 9 9
9 9
8 8th
8 8th
8 8th
0,56 0.56
9 9
8 8th
8 8th
8 8th
9 9
9 6 9 6
9 9 9 9
9 9
8 8th
8 8th
8 8th
0,28 0.28
8 8th
6 6
7 7
7 7
8 8th
6 3 6 3
8 8 8 8
8 8th
7 7
8 8th
8 8th
0,14 0.14
9 9
5 5
7 7
3 3rd
7 7
3 0 3 0
0 7 0 7
7 7
6 6
7 7
7 7
CHj CHj
CH(CH3)2 CH (CH3) 2
-CHj-C=CH2 -CHj-C = CH2
H 11,2 H 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9 9 9
9 8 9 8
] ]
2,24 2.24
9 9
8 8th
8 8th
9 9
8 8th
9 9 9 9
9 8 9 8
9 9
8 8th
8 8th
8 8th
(H-)-Isomer (H -) isomer
Cl Cl
1,12 1.12
9 9
8 8th
8 8th
8 8th
9 9
8 9 8 9
9 8 9 8
9 9
8 8th
8 8th
8 8th
0,56 0.56
9 9
8 8th
7 7
7 7
8 8th
7 5 7 5
8 8 8 8
8 8th
8 8th
7 7
8 8th
0,28 0.28
9 9
2 2nd
7 7
5 5
8 8th
5 2 5 2
7 8 7 8
8 8th
8 8th
7 7
8 8th
0,14 0.14
6 6
0 0
7 7
3 3rd
5 5
3 0 3 0
2 7 2 7
3 3rd
6 6
6 6
8 8th
0,07 0.07
3 3rd
0 0
6 6
0 0
2 2nd
0 0 0 0
0 3 0 3
2 2nd
3 3rd
3 3rd
7 7
CH, CH,
CH(CHj)2 CH (CHj) 2
-CH(CHj)CH=CHCH3 -CH (CHj) CH = CHCH3
4(5)11,2 4 (5) 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
8 8 8 8
9 8 9 8
CH3 2,24 CH3 2.24
9 9
8 8th
7 7
8 8th
8 8th
6 6 6 6
7 9 7 9
8 8th
5 5
7 7
8 8th
1,12 1.12
9 9
6 6
6 6
7 7
6 6
3 0 3 0
2 8 2 8
5 5
2 2nd
6 6
8 8th
0,56 0.56
9 9
3 3rd
2 2nd
3 3rd
3 3rd
0 0 0 0
0 7 0 7
0 0
0 0
5 5
3 3rd
CHj CHj
CH(CH3)2 CH (CH3) 2
-ch3 -ch3
3 (6)11,2 3 (6) 11.2
0 0
0 0
8 8th
9 9
0 0
7 7
7 7
7 7
0 0 0 0
0 0 0 0
Cl Cl
CH, CH,
CH(CHj)2 CH (CHj) 2
-ch2c=ch -ch2c = ch
3 (6)11,2 3 (6) 11.2
7 7
0 0
8 8th
9 9
6 6
8 8th
8 8th
8 8th
0 0 0 0
0 0 0 0
Cl Cl
CH., CH.,
CH(CH3)2 CH (CH3) 2
-ch2c=c-ch2oh -ch2c = c-ch2oh
H 11,2 H 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9 9 9
9 8 9 8
2,24 2.24
9 9
8 8th
8 8th
8 8th
8 8th
7 9 7 9
9 8 9 8
9 9
8 8th
8 8th
8 8th
1,12 1.12
9 9
5 5
8 8th
7 7
8 8th
3 6 3 6
8 8 8 8
8 8th
7 7
8 8th
8 8th
0,56 0.56
9 9
0 0
8 8th
5 5
3 3rd
2 2 2 2
7 7 7 7
7 7
6 6
7 7
7 7
0,28 0.28
9 9
0 0
8 8th
2 2nd
3 3rd
0 0 0 0
0 3 0 3
2 2nd
3 3rd
7 7
5 5
CH., CH.,
CH(CHj)2 CH (CHj) 2
-ch2-c=ch2 -ch2-c = ch2
3 (6)11,2 3 (6) 11.2
0 0
0 0
9 9
9 9
0 0
6 6
7 7
6 6
0 0 0 0
0 0 0 0
1 1
Cl Cl
Cl Cl
CH, CH,
CH(CH3)2 CH (CH3) 2
-CH(CH,)2CH=CH-CH, -CH (CH,) 2CH = CH-CH,
3 (6)11,2 3 (6) 11.2
0 0
0 0
8 8th
9 9
0 0
4 4th
7 7
8 8th
0 0 0 0
0 0 0 0
Cl Cl
639 957 639 957
20 20th
Formel Anwen- Pflanzenarten dungs-menge Formula application quantity of plants
R! R, R, X in kg/ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI R! R, R, X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI
ch., ch.,
ch(ch3)2 ch (ch3) 2
-qhs -qhs
3 (6)11,2 3 (6) 11.2
5 5
0 0
8 8th
8 8th
1 1
8 8th
7 7
7 7
7 7
7 7
0 0
2 2nd
no2 no2
ch3 ch3
c2hj c2hj
-ch3 -ch3
h H
11,2 11.2
9 9
5 5
9 9
8 8th
0 0
8 8th
8 8th
9 9
7 7
0 0
8 8th
9 9
2,24 2.24
7 7
0 0
8 8th
8 8th
9 9
3 3rd
0 0
3 3rd
8 8th
5 5
6 6
7 7
1,12 1.12
2 2nd
0 0
7 7
7 7
8 8th
0 0
0 0
0 0
7 7
0 0
3 3rd
5 5
ch3 ch3
c3h5 c3h5
-ch2-c=ch h -ch2-c = ch h
11,2 11.2
9 9
8 8th
9 9
9 9
3 3rd
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
9 9
2,24 2.24
9 9
0 0
8 8th
8 8th
9 9
7 7
6 6
9 9
8 8th
7 7
7 7
7 7
1,12 1.12
9 9
0 0
8 8th
6 6
8 8th
3 3rd
2 2nd
3 3rd
6 6
3 3rd
5 5
6 6
0,56 0.56
3 3rd
0 0
7 7
5 5
5 5
0 0
0 0
0 0
0 0
0 0
2 2nd
2 2nd
ch3 ch3
c2h5 c2h5
-ch2-c=ch, -ch2-c = ch,
h H
11,2 11.2
9 9
7 7
9 9
9 9
8 8th
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
1 1
2,24 2.24
9 9
0 0
8 8th
8 8th
8 8th
6 6
6 6
8 8th
8 8th
5 5
7 7
6 6
cl cl
1,12 1.12
7 7
0 0
8 8th
6 6
2 2nd
3 3rd
0 0
6 6
6 6
3 3rd
5 5
3 3rd
0,56 0.56
5 5
0 0
7 7
0 0
1 1
0 0
0 0
7 7
2 2nd
1 1
3 3rd
2 2nd
0,28 0.28
2 2nd
0 0
3 3rd
0 0
0 0
0 0
0 0
0 0
0 0
0 0
1 1
0 0
ch3 ch3
ch(ch3)2 ch (ch3) 2
-CHi-C=CHCl h -CHi-C = CHCl h
11,2 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
9 9
9 9
9 9
9 9
9 9
8 8th
" 1 " 1
2,24 2.24
9 9
8 8th
8 8th
8 8th
9 9
9 9
9 9
9 9
8 8th
8 8th
8 8th
8 8th
Cl Cl
1,12 1.12
9 9
2 2nd
8 8th
7 7
8 8th
8 8th
5 5
8 8th
7 7
7 7
7 7
8 8th
0,56 0.56
9 9
0 0
6 6
6 6
7 7
3 3rd
2 2nd
5 5
3 3rd
7 7
6 6
7 7
0,28 0.28
8 8th
0 0
2 2nd
5 5
6 6
0 0
0 0
0 0
0 0
1 1
5 5
7 7
ch3 ch3
QHs ch3 QHs ch3
11,2 11.2
9 9
6 6
9 9
9 9
0 0
8 8th
8 8th
9 9
8 8th
7 7
8 8th
8 8th
1 1
2,24 2.24
9 9
0 0
8 8th
8 8th
8 8th
5 5
2 2nd
5 5
3 3rd
7 7
7 7
7 7
-ch-ch=ch-ch3 -ch-ch = ch-ch3
h H
1,12 1.12
9 9
0 0
7 7
5 5
2 2nd
2 2nd
0 0
2 2nd
0 0
2 2nd
5 5
5 5
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch,-c=ch2 -ch, -c = ch2
3 (6) 11,2 3 (6) 11.2
5 5
0 0
8 8th
8 8th
6 6
7 7
8 8th
8 8th
5 5
0 0
6 6
5 5
" 1 " 1
no, no,
Cl Cl
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
11,2 11.2
9 9
7 7
9 9
9 9
8 8th
7 7
8 8th
9 9
8 8th
9 9
8 8th
8 8th
1 1
2,24 2.24
9 9
8 8th
8 8th
8 8th
9 9
9 9
8 8th
9 9
8 8th
9 9
8 8th
8 8th
-c-ch=ch2 -c-ch = ch2
h H
1,12 1.12
9 9
0 0
8 8th
7 7
7 7
3 3rd
7 7
9 9
6 6
8 8th
7 7
6 6
1 1
0,56 0.56
8 8th
0 0
7 7
3 3rd
8 8th
0 0
0 0
8 8th
5 5
7 7
5 5
5 5
qhs qhs
0,28 0.28
9 9
0 0
7 7
5 5
3 3rd
0 0
0 0
8 8th
3 3rd
6 6
3 3rd
2 2nd
0,14 0.14
9 9
0 0
2 2nd
0 0
1 1
0 0
0 0
0 0
0 0
6 6
2 2nd
1 1
ch3 ch3
c2h5 c2h5
ch3 ch3
11,2 11.2
9 9
0 0
8 8th
8 8th
0 0
8 8th
8 8th
8 8th
7 7
8 8th
8 8th
8 8th
1 1
2,24 2.24
9 9
0 0
8 8th
8 8th
9 9
7 7
5 5
9 9
5 5
8 8th
8 8th
8 8th
-c-ch=ch, -c-ch = ch,
h H
1,12 1.12
9 9
0 0
7 7
7 7
7 7
2 2nd
1 1
6 6
2 2nd
5 5
6 6
7 7
1 1
0,56 0.56
7 7
0 0
5 5
3 3rd
1 1
0 0
0 0
0 0
0 0
1 1
2 2nd
5 5
ch3 ch3
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch(ch3), ch (ch3),
h H
11,2 11.2
9 9
9 9
8 8th
9 9
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
7 7
1 1
2,24 2.24
7 7
0 0
7 7
8 8th
8 8th
6 6
7 7
8 8th
3 3rd
3 3rd
5 5
5 5
-c-c=ch -c-c = ch
1,12 1.12
3 3rd
0 0
6 6
6 6
8 8th
5 5
6 6
7 7
0 0
0 0
3 3rd
2 2nd
1 1
0,56 0.56
0 0
0 0
3 3rd
5 5
3 3rd
0 0
6 6
0 0
0 0
1 1
1 1
ch(ch3)2 ch (ch3) 2
ch3 ch3
ch(ch3)2 ch (ch3) 2
-C2hs -C2hs
4 (5)11,2 4 (5) 11.2
8 8th
1 1
8 8th
9 9
8 8th
8 8th
7 7
9 9
6 6
3 3rd
7 7
7 7
Cl Cl
2,24 2.24
2 2nd
7 7
5 5
6 6
3 3rd
1 1
3 3rd
8 8th
0 0
6 6
3 3rd
1,12 1.12
1 1
0 0
5 5
5 5
2 2nd
0 0
0 0
1 1
8 8th
0 0
3 3rd
0 0
QHS QHS
ch(ch3)2 ch (ch3) 2
-ch3 -ch3
h H
11,2 11.2
3 3rd
0 0
8 8th
8 8th
0 0
6 6
3 3rd
6 6
1 1
1 1
1 1
1 1
c2h5 c2h5
ch(ch3)2 ch (ch3) 2
-ch2-c=ch h -ch2-c = ch h
11,2 11.2
7 7
0 0
8 8th
9 9
0 0
8 8th
8 8th
8 8th
7 7
6 6
8 8th
8 8th
c,h5 c, h5
ch(ch3)2 ch (ch3) 2
-ch2-c=ch2 -ch2-c = ch2
h H
11,2 11.2
3 3rd
0 0
8 8th
9 9
0 0
8 8th
8 8th
8 8th
6 6
7 7
8 8th
5 5
Cl Cl
ch3 ch3
ch(ch3)2 ch (ch3) 2
h H
4(5)11,2 4 (5) 11.2
9 9
8 8th
9 9
9 9
8 8th
8 8th
8 8th
9 9
9 9
9 9
9 9
9 9
Cl Cl
2,24 2.24
9 9
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
7 7
1,12 1.12
9 9
8 8th
8 8th
7 7
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
7 7
0,56 0.56
9 9
6 6
8 8th
7 7
8 8th
6 6
3 3rd
8 8th
8 8th
7 7
7 7
7 7
0,28 0.28
9 9
6 6
7 7
8 8th
7 7
5 5
3 3rd
5 5
6 6
5 5
5 5
6 6
0,14 0.14
9 9
0 0
5 5
3 3rd
6 6
3 3rd
1 1
2 2nd
5 5
3 3rd
3 3rd
5 5
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch2-c=ch -ch2-c = ch
4 (5)11,2 4 (5) 11.2
9 9
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
9 9
8 8th
Cl Cl
2,24 2.24
8 8th
8 8th
8 8th
7 7
8 8th
8 8th
7 7
8 8th
6 6
8 8th
5 5
1,12 1.12
6 6
7 7
8 8th
5 5
7 7
7 7
7 7
8 8th
1 1
0 0
5 5
0,56 0.56
5 5
7 7
8 8th
2 2nd
5 5
5 5
6 6
7 7
0 0
1 1
1 1
0,28 0.28
3 3rd
7 7
7 7
0 0
2 2nd
0 0
3 3rd
7 7
0 0
0 0
1 1
JW JW
9 9
8 8th
9 9
8 8th
8 8th
8 8th
7 7
7 7
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
3 3rd
8 8th
8 8th
0 0
9 9
8 8th
7 7
8 8th
8 8th
8 8th
8 8th
5 5
8 8th
8 8th
8 8th
8 8th
21 21st
639 957 639 957
Formel R, Formula R,
R, R,
R3 R3
X X
Anwendungs-menge in kg/ha Application quantity in kg / ha
Pflanzenarten PN SE MU PI Plant species PN SE MU PI
RW MG TW VL RW MG TW VL
BA BA
CR CR
FO FO
WOCN WOCN
CO CO
SY RI SY RI
JW JW
ch, ch,
ch(ch3)2 ch (ch3) 2
ch3 ch3
4(5)11,2 4 (5) 11.2
9 8 8 8 9 8 8 8
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
1 1
2,24 2.24
9 Cl 9 cl
8 8th
7 7
2 2nd
6 6
7 7
7 7
7 7
7 7
6 6
5 5
6 6
7 7
-ch-ch=chch3 -ch-ch = chch3
1,12 1.12
6 6
7 7
3 3rd
0 0
7 7
0 0
5 5
2 2nd
2 2nd
1 1
5 5
3 3rd
0,56 0.56
2 2nd
0 0
5 5
0 0
6 6
0 0
2 2nd
2 2nd
0 0
0 0
3 3rd
0 0
ch3 ch3
c2h5 c2h5
h h h h
11,2 11.2
9 8 8 8 9 8 8 8
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
2,24 2.24
9 9
0 0
8 8th
8 8th
9 9
9 9
9 9
8 8th
8 8th
9 9
9 9
8 8th
1,12 1.12
9 9
0 0
8 8th
8 8th
8 8th
9 9
9 9
9 9
8 8th
7 7
9 9
8 8th
8 8th
0,56 0.56
9 9
0 0
8 8th
7 7
1 1
1 1
3 3rd
5 5
3 3rd
3 3rd
8 8th
8 8th
0,28 0.28
9 9
0 0
7 7
5 5
1 1
1 1
5 5
2 2nd
3 3rd
3 3rd
7 7
7 7
c2h5 c2h5
ch(ch3)2 ch (ch3) 2
h h h h
11,2 11.2
9 0 8 8 9 0 8 8
3 3rd
8 8th
8 8th
8 8th
7 7
8 8th
8 8th
5 5
2,24 2.24
9 9
0 0
8 8th
2 2nd
3 3rd
2 2nd
7 7
0 0
3 3rd
6 6
5 5
7 7
1,12 1.12
8 8th
0 0
6 6
0 0
7 7
0 0
0 0
3 3rd
0 0
3 3rd
5 5
2 2nd
1 1
0,56 0.56
9 9
0 0
3 3rd
0 0
0 0
0 0
0 0
0 0
0 0
1 1
2 2nd
2 2nd
0 0
ch3 ch3
ch(ch3)2 ch (ch3) 2
h H
3 (6)11,2 3 (6) 11.2
9 8 8 8 9 8 8 8
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
9 9
8 8th
Cl Cl
2,24 2.24
9 9
9 9
8 8th
7 7
8 8th
9 9
8 8th
8 8th
9 9
9 9
8 8th
8 8th
1,12 1.12
9 9
8 8th
8 8th
3 3rd
7 7
6 6
3 3rd
7 7
7 7
8 8th
8 8th
8 8th
0,56 0.56
9 9
7 7
8 8th
2 2nd
3 3rd
1 1
1 1
2 2nd
6 6
8 8th
8 8th
7 7
0,28 0.28
9 9
7 7
8 8th
2 2nd
1 1
0 0
0 0
2 2nd
2 2nd
8 8th
7 7
7 7
ch3 ch3
ch(ch3)2 ch (ch3) 2
-ch,-c=ch2 -ch, -c = ch2
4(5)11,2 4 (5) 11.2
9 8 8 9 9 8 8 9
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
8 8th
" 1 " 1
Cl Cl
2,24 2.24
9 9
8 8th
8 8th
7 7
7 7
9 9
9 9
8 8th
8 8th
7 7
8 8th
7 7
8 8th
cl cl
1,12 1.12
9 9
8 8th
5 5
6 6
8 8th
8 8th
7 7
8 8th
2 2nd
5 5
5 5
8 8th
0,56 0.56
8 8th
7 7
1 1
5 5
7 7
8 8th
6 6
5 5
0 0
6 6
2 2nd
8 8th
0,28 0.28
5 5
7 7
0 0
0 0
5 5
5 5
5 5
2 2nd
0 0
3 3rd
2 2nd
8 8th
0,13 0.13
0 0
7 7
3 3rd
0 0
0 0
0 0
3 3rd
3 3rd
0 0
0 0
3 3rd
1 1
7 7
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch2=ch2 ch2 = ch2
h H
11,2 11.2
9 9 8 8 9 9 8 8
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
9 9
8 8th
1 1
2,24 2.24
9 9
8 8th
8 8th
9 9
9 9
9 9
9 9
8 8th
9 9
8 8th
8 8th
8 8th
-ch-ch=ch -ch-ch = ch
1,12 1.12
9 9
8 8th
8 8th
8 8th
8 8th
9 9
9 9
9 9
8 8th
7 7
8 8th
7 7
8 8th
0,56 0.56
9 9
8 8th
8 8th
8 8th
8 8th
9 9
8 8th
8 8th
8 8th
7 7
8 8th
7 7
8 8th
0,28 0.28
9 9
7 7
7 7
7 7
7 7
8 8th
7 7
6 6
5 5
8 8th
7 7
8 8th
0,14 0.14
9 9
7 7
5 5
7 7
7 7
8 8th
7 7
5 5
2 2nd
8 8th
6 6
8 8th
0,07 0.07
9 9
5 5
5 5
6 6
7 7
8 8th
6 6
3 3rd
2 2nd
7 7
2 2nd
7 7
ch3 ch3
ch(ch3)2 ch (ch3) 2
ch3 ch3
4(5)11,2 4 (5) 11.2
9 7 8 8 9 7 8 8
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
1 1
2,24 2.24
9 9
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
8 8th
-c-ch=ch2 -c-ch = ch2
1,12 1.12
9 9
8 8th
5 5
5 5
7 7
8 8th
7 7
6 6
3 3rd
9 9
7 7
8 8th
1 1
cl cl
0,56 0.56
8 8th
8 8th
5 5
3 3rd
7 7
7 7
6 6
2 2nd
3 3rd
8 8th
7 7
7 7
ch3 ch3
0,28 0.28
8 8th
0 0
7 7
1 1
1 1
0 0
1 1
5 5
0 0
2 2nd
5 5
6 6
5 5
* = Mittelwert aus zwei oder mehr Versuchen Beispiel 8 * = Average of two or more experiments Example 8
Wirksamkeit als selektive Nachauflaufherbizide Die Wirksamkeit der erfindungsgemässen Verbindungen als selektive Nachauflaufherbizide wird durch die folgenden Untersuchungen gezeigt, bei denen man Sorghumpflanzen [Sorghum bicolor (L) Woeuch], Frühjahrsweizenpflanzen (Triticum aestiv-um, cv. Auza) und Gerstenpflanzen (Hordeum vulgare, cv. Efficacy as selective post-emergence herbicides The effectiveness of the compounds according to the invention as selective post-emergence herbicides is shown by the following tests, in which sorghum plants [Sorghum bicolor (L) Woeuch], spring wheat plants (Triticum aestiv-um, cv. Auza) and barley plants (Hordeum vulgare, cv .
43 Steptoe) mit entsprechenden Wirkstoffen behandelt, die in Gemischen aus Wasser und Aceton dispergiert sind. Es wird im einzelnen nach dem in Beispiel 6 beschriebenen Verfahren gearbeitet, wobei die behandelten Pflanzen wie in Beispiel 6 angegeben untersucht und nach der dortigen Beurteilungsskala 50 bewertet werden. Die bei diesen Versuchen erhaltenen Ergebnisse gehen aus der folgenden Tabelle III hervor. 43 Steptoe) treated with the corresponding active ingredients, which are dispersed in mixtures of water and acetone. The procedure described in Example 6 is followed in detail, the treated plants being examined as indicated in Example 6 and evaluated according to the evaluation scale 50 there. The results obtained in these experiments are shown in Table III below.
Tabelle III Table III
Wirksamkeit der Verbindungen der angegebenen Formel als selektive Nachauflaufherbizide Efficacy of the compounds of the formula given as selective post-emergence herbicides
:oor- : oor-
Formel formula
R> R>
R3 R3
Anwendungsmenge in kg/ha Application amount in kg / ha
Pflanzenarten Sorghum Auza Plant species sorghum auza
Steptoe Steptoe
-CH, -CH(CH3), -CH, -CH (CH3),
-CHiCHIOCH, -CHiCHIOCH,
H H
2,24 1,12 0,56 2.24 1.12 0.56
639 957 639 957
22 22
Formel formula
R, R, R, R,
Rs Rs
X X
Anwendungsmenge in kg/ha Application amount in kg / ha
Pflanzenarten Sorghum Auza Plant species sorghum auza
Steptoe Steptoe
-ch, -ch(ch,)2 -ch, -ch (ch,) 2
-ch, -ch,
-ch3 -ch3
-CH, -CH,
-CH, -CH,
-CH, -CH,
-ch, -ch,
-CH, -CH,
-CH, -CH,
-CH, -CH,
-CH, -CH,
-ch, -ch,
-CH, -CH,
-CH(CH3)2 -CH(CH3)2 -CH(CH3)2 -CH (CH3) 2 -CH (CH3) 2 -CH (CH3) 2
-CH(CH3)2 -CH(CH3)2 -CH(CH3)2 -CH (CH3) 2 -CH (CH3) 2 -CH (CH3) 2
(+)-Isomer (+) - isomer
-CH(CH3)2 -CH (CH3) 2
-CH(CH3)2 -CH (CH3) 2
-C2Hs -C2Hs
-CH(CH3)2 -CH (CH3) 2
-CH(CH3)2 -CH (CH3) 2
-CH(CH3)2 -CH (CH3) 2
CH, CH,
I ' I '
-c-c2h5 ch3 -c-c2h5 ch3
-ch2ch2oc2hs -ch2ch2oc2hs
-çh<j ch3 -çh <j ch3
-CH2-C=C-C7H15-n ch(ch3)2 -CH2-C = C-C7H15-n ch (ch3) 2
-CH, -CH,
-c2h5 -c2h5
-ch2-c=ch -ch2-c = ch
-c2h5 -c2h5
-ch3 -ch3
-ch,-c=ch, -ch, -c = ch,
" I " "I"
Cl Cl
-c2h5 ch3 -c2h5 ch3
-ch-ch=chch3 -ch-ch = chch3
H H H H
H H
H H
H H
2,24 1,12 0,56 2.24 1.12 0.56
2,24 1,12 0,56 2,24 1,12 0,56 2,24 1,12 0,56 2.24 1.12 0.56 2.24 1.12 0.56 2.24 1.12 0.56
H H
2,24 1,12 1,12 4(5)CH3 2,24 1,12 0,56 H 2,24 1,12 0,56 3(6)CI 2,24 1,12 0,56 3(6)N02 2,24 1,12 0,56 H 2,24 1,12 0,56 3(6)NO, 2,24 1,12 0,56 4(5)C12,24 1,12 0,56 4(5)C12,24 1,12 0,56 2.24 1.12 1.12 4 (5) CH3 2.24 1.12 0.56 H 2.24 1.12 0.56 3 (6) CI 2.24 1.12 0.56 3 (6 ) N02 2.24 1.12 0.56 H 2.24 1.12 0.56 3 (6) NO, 2.24 1.12 0.56 4 (5) C12.24 1.12 0.56 4 (5) C12.24 1.12 0.56
3 3 0 3 0 0 2 0 0 3 3 0 3 0 0 2 0 0
0 0 0 2 2 0 0 0 2 2
0 2 0 2
1 0 1 0
2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6
3 0 3 0
2 2nd
2 0 6 5 2 0 6 5
3 3 2 3 3 2
2 2nd
3 0 3 0
0 0
1 0 0 9 1 0 0 9
2 2nd
2 0 2 0
3 0 0 0 0 0 3 0 0 0 0 0
2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0
0 0
6 6
7 7
1 0 0 0 0 0 0 1 0 0 0 0 0 0
50 50
Beispiel 9 pflanzen [Sorghum bicolor (L) Moeuch], Frühjahrsweizenpflan zen (Triticum aestivum, cv. Auza) und Gerstenpflanzen (Hor-deum vulgare, cv. Steptoe). Die Bewertung der Versuchsergeb-Nach dem in Beispiel 7 beschriebenen Verfahren untersucht nisse wird nach der in Beispiel 6 angegebenen Beurteilungsskala man die Wirksamkeit der erfindungsgemässen Verbindungen als 55 durchgeführt. Die bei diesen Versuchen erhaltenen Ergebnisse selektive Vorauflaufherbizide unter Verwendung von Sorghum- gehen aus folgender Tabelle IV hervor. Example 9 plants [Sorghum bicolor (L) Moeuch], spring wheat plants (Triticum aestivum, cv. Auza) and barley plants (Hor-deum vulgare, cv. Steptoe). The evaluation of the test results. According to the method described in Example 7, the effectiveness of the compounds according to the invention is carried out as 55 on the evaluation scale given in Example 6. The results obtained in these trials of selective pre-emergence herbicides using sorghum are shown in Table IV below.
Wirksamkeit als selektive Vorauflaufherbizide Efficacy as selective pre-emergence herbicides
Tabelle IV Table IV
Wirksamkeit der Verbindungen der angegebenen Formel als selektive Vorauflaufherbizide Efficacy of the compounds of the formula given as selective pre-emergence herbicides
23 23
639 957 639 957
Formel formula
Anwendungsmenge Application amount
Pflanzenarten Plant species
R, R,
R: R:
R3 R3
X X
in kg/ha in kg / ha
Sorghum Sorghum
Auza Auza
Steptoe Steptoe
-CH., -CH.,
-CH(CHj)2 -CH (CHj) 2
-CH2C(CHj)j -CH2C (CHj) j
H H
2,24 2.24
0 0
2 2nd
0 0
1,12 1.12
0 0
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CH, -CH,
-CH(CHj)2 -CH (CHj) 2
-CH2CH,OCHj -CH2CH, OCHj
H H
2,24 2.24
0 0
7 7
2 2nd
1,12 1.12
0 0
3 3rd
0 0
0,56 0.56
0 0
0 0
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-céhij-n -céhij-n
H H
2,24 2.24
3 3rd
2 2nd
0 0
1,12 1.12
0 0
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
CHj CHj
H H
2,24 2.24
2 2nd
5 5
2 2nd
1 1
1,12 1.12
0 0
3 3rd
0 0
-C-QHs -C-QHs
1 1
0,56 0.56
0 0
0 0
0 0
CHj CHj
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-CH2CH2OC2Hs -CH2CH2OC2Hs
H H
2,24 2.24
2 2nd
8 8th
7 7
1,12 1.12
0 0
5 5
0 0
0,56 0.56
0 0
3 3rd
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-CH2CH=CH-C6Hs -CH2CH = CH-C6Hs
H H
2,24 2.24
3 3rd
7 7
3 3rd
1,12 1.12
2 2nd
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CH, -CH,
-CH(CHj)2 -CH (CHj) 2
-CHj -CHj
4(5)CHj 2,24 4 (5) CHj 2.24
8 8th
2 2nd
3 3rd
1,12 1.12
8 8th
0 0
0 0
0,56 0.56
2 2nd
0 0
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-ch2-ch2- -ch2-ch2-
h H
2,24 2.24
0 0
6 6
3 3rd
1,12 1.12
0 0
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CHj -CHj
-QHs -QHs
-CHj -CHj
H H
2,24 2.24
2 2nd
2 2nd
2 2nd
1,12 1.12
0 0
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-c2h5 -c2h5
4(5)C12,24 4 (5) C12.24
0 0
7 7
0 0
1,12 1.12
0 0
0 0
0 0
0,56 0.56
0 0
0 0
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
ÇH(CHj)2 ÇH (CHj) 2
H H
2,24 2.24
5 5
6 6
2 2nd
1 1
1,12 1.12
0 0
3 3rd
0 0
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
-C-C=CH -C-C = CH
0,56 0.56
0 0
0 0
0 0
CH(CHj)2 CH (CHj) 2
-CHj -CHj
-CH(CHj)2 -CH (CHj) 2
CHj CHj
4(5)CI 2,24 4 (5) CI 2.24
8 8th
7 7
2 2nd
1 1
1,12 1.12
2 2nd
5 5
0 0
-CH-CH=CHCHj -CH-CH = CHCHj
0,56 0.56
1 1
2 2nd
0 0
M M
Claims (18)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US82245877A | 1977-08-08 | 1977-08-08 | |
US05/822,459 US4122275A (en) | 1977-08-08 | 1977-08-08 | Imidazolinyl benzamides as herbicidal agents |
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CH639957A5 true CH639957A5 (en) | 1983-12-15 |
Family
ID=27124643
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CH828978A CH639957A5 (en) | 1977-08-08 | 1978-08-03 | IMIDAZOLINYLBENZOATE. |
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JP (1) | JPS5464637A (en) |
AR (1) | AR222973A1 (en) |
AT (1) | AT364571B (en) |
AU (1) | AU518293B2 (en) |
BG (1) | BG32411A3 (en) |
BR (1) | BR7805062A (en) |
CA (1) | CA1109878A (en) |
CH (1) | CH639957A5 (en) |
CS (1) | CS204033B2 (en) |
DD (1) | DD138595A5 (en) |
DE (1) | DE2833274A1 (en) |
DK (1) | DK157927C (en) |
ES (2) | ES472433A1 (en) |
FR (1) | FR2400018A1 (en) |
GB (1) | GB2004537B (en) |
GR (1) | GR72789B (en) |
HU (1) | HU181841B (en) |
IL (1) | IL55064A (en) |
IT (1) | IT1107482B (en) |
NL (1) | NL7808228A (en) |
NZ (1) | NZ187812A (en) |
SE (1) | SE448729B (en) |
UA (1) | UA6015A1 (en) |
YU (2) | YU41316B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0133310A1 (en) * | 1983-08-02 | 1985-02-20 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
EP0298029A1 (en) * | 1987-07-01 | 1989-01-04 | Ciba-Geigy Ag | Substituted imidazolones with a herbicidal activity |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0133311A3 (en) * | 1983-08-02 | 1987-12-23 | American Cyanamid Company | Substituted imidazolinyl benzoic acids, esters and salts and use thereof as herbicidal agents |
DE3340594A1 (en) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | 2-ARYL-SUBSTITUTED IMIDAZOLINONES, METHOD FOR THEIR PRODUCTION AND THEIR USE IN PLANT PROTECTION |
DE3340595A1 (en) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | IMIDAZOLINONES, METHOD FOR THEIR PRODUCTION AND THEIR USE IN PLANT PROTECTION |
DE3345901A1 (en) * | 1983-12-20 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | 1-ACYLIMIDAZOLINONE, METHOD FOR THE PRODUCTION AND THEIR USE IN AGRICULTURE |
ATE64597T1 (en) * | 1984-02-10 | 1991-07-15 | American Cyanamid Co | REGIO AND OPTICAL ISOMERS OF IMIDAZOLINYLTOLUOLIC ACID, ITS ESTER AND SALTS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS HERBICIDES. |
GB8507808D0 (en) * | 1985-03-26 | 1985-05-01 | Shell Int Research | Heterocyclic herbicides |
US4726835A (en) * | 1985-12-02 | 1988-02-23 | Idemitsu Kosan Company Limited | Herbicidal and plant growth regulating imidazoline derivatives |
EP0412577A1 (en) | 1986-05-09 | 1991-02-13 | Hoechst Aktiengesellschaft | Herbicidal agent |
DE3938564A1 (en) * | 1989-11-21 | 1991-05-23 | Hoechst Ag | HERBICIDAL AGENTS |
US5525578A (en) * | 1989-11-21 | 1996-06-11 | Hoechst Aktiengesellschaft | Herbicidal agents containing imidazole herbicide and ether sulfate surfactants |
US5062881A (en) * | 1989-12-20 | 1991-11-05 | American Cyanamid Company | 2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation |
US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
US8367669B2 (en) | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
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DE1176660B (en) * | 1963-07-05 | 1964-08-27 | Beiersdorf & Co A G P | Process for the preparation of triaryl-substituted imidazolinones-4 (5) |
US3645965A (en) * | 1967-10-23 | 1972-02-29 | Sankyo Co | Stabilization of synthetic polymers with imidazolidine compounds |
US3687971A (en) * | 1970-06-22 | 1972-08-29 | Merck & Co Inc | 4-(pyrrolyl)-salicylic acid derivatives |
-
1978
- 1978-07-03 IL IL55064A patent/IL55064A/en active IP Right Grant
- 1978-07-07 AU AU37867/78A patent/AU518293B2/en not_active Expired
- 1978-07-07 GR GR56732A patent/GR72789B/el unknown
- 1978-07-10 NZ NZ187812A patent/NZ187812A/en unknown
- 1978-07-17 AR AR272981A patent/AR222973A1/en active
- 1978-07-20 CA CA307,740A patent/CA1109878A/en not_active Expired
- 1978-07-24 YU YU1758/78A patent/YU41316B/en unknown
- 1978-07-25 IT IT50457/78A patent/IT1107482B/en active Protection Beyond IP Right Term
- 1978-07-26 GB GB7831112A patent/GB2004537B/en not_active Expired
- 1978-07-28 DE DE19782833274 patent/DE2833274A1/en active Granted
- 1978-08-03 CH CH828978A patent/CH639957A5/en not_active IP Right Cessation
- 1978-08-04 NL NL787808228A patent/NL7808228A/en unknown
- 1978-08-07 SE SE7808451A patent/SE448729B/en not_active IP Right Cessation
- 1978-08-07 BR BR7805062A patent/BR7805062A/en unknown
- 1978-08-07 DK DK348278A patent/DK157927C/en not_active IP Right Cessation
- 1978-08-07 BG BG040610A patent/BG32411A3/en unknown
- 1978-08-08 AT AT0577478A patent/AT364571B/en active
- 1978-08-08 UA UA2646369A patent/UA6015A1/en unknown
- 1978-08-08 FR FR7823383A patent/FR2400018A1/en active Granted
- 1978-08-08 DD DD78207175A patent/DD138595A5/en not_active IP Right Cessation
- 1978-08-08 HU HU78AE540A patent/HU181841B/en unknown
- 1978-08-08 ES ES472433A patent/ES472433A1/en not_active Expired
- 1978-08-08 CS CS785182A patent/CS204033B2/en unknown
- 1978-08-08 JP JP9658178A patent/JPS5464637A/en active Granted
-
1979
- 1979-04-10 ES ES479467A patent/ES479467A1/en not_active Expired
-
1982
- 1982-10-07 YU YU2255/82A patent/YU40967B/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0133310A1 (en) * | 1983-08-02 | 1985-02-20 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
EP0298029A1 (en) * | 1987-07-01 | 1989-01-04 | Ciba-Geigy Ag | Substituted imidazolones with a herbicidal activity |
US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
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Legal Events
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PL | Patent ceased |