USRE32489E - Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones - Google Patents
Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones Download PDFInfo
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- USRE32489E USRE32489E US06/771,086 US77108685A USRE32489E US RE32489 E USRE32489 E US RE32489E US 77108685 A US77108685 A US 77108685A US RE32489 E USRE32489 E US RE32489E
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
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- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
Definitions
- U.S. Pat. No. 4,011,256 discloses herbicidal cyclohexane-1,3-diones.
- This invention relates to novel herbicidal compounds, compositions and methods of use thereof. It has been found that novel haloalkyl, haloalkenyl and haloaryl-substituted 2-[1-(oxyamino)-alkylidene]-cyclohexane-1,3-diones are particularly useful as grassy herbicides in both pre- and post-emergent applications.
- the compounds of the invention have the structural formula (I): ##STR1## wherein R is alkyl of 1 to 6 carbon atoms or phenyl;
- R 1 is haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, haloaryl of 6 to 10 carbon atoms, halobenzyl, all of which contain 1 to 3 halogen atoms; cycloalkyl of 5 to 7 carbon atoms or benzyl substituted with 1 to 3 alkyl groups of 1 to 4 carbon atoms or haloalkyl groups of 1 to 4 carbon atoms and 1 to 9 halogen atoms;
- R 2 and R 3 are independently hydrogen, alkyl of 1 to 3 carbon atoms, alkylthio of 1 to 6 carbon atoms, or alkylthioalkyl of 2 to 8 carbon atoms;
- R 4 is hydrogen, or carbalkoxy of 2 to 4 carbon atoms
- R 5 is hydrogen, a cation, or ##STR2## wherein R 6 is alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms.
- a particularly preferred class of compounds within the scope of the invention are substituted 2-[1-(oxyamino)-alkylidene]-5,5-dialkylcyclohexane-1,3-diones.
- R groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isopentyl, neopentyl, n-hexyl and phenyl.
- R is alkyl of 1 to 6 carbon atoms. Most preferably R is alkyl of 1 to 3 carbon atoms. Most preferably R is ethyl or propyl.
- R 1 groups are chloromethyl, bromomethyl, fluoromethyl, 2-chloroethyl, 2-bromoethyl, 3,4-dichlorobutyl, 6-chlorohexyl, 3-cis-chloroallyl, 2,3-cis-dichloroallyl, 2-chloroallyl, 4,4-dichloro-but-3-enyl, 4-bromo-3-bromomethyl-but-2-enyl 5,5-dibromo-4-methyl-pent-2-enyl, 2,5-dichloro-hex-3-enyl, p-fluorophenyl, p-fluorobenzyl, p-chlorobenzyl, p-bromophenyl, p-bromobenzyl, 3,4-dichlorophenyl, 3,4-dichlorobenzyl, 2-fluorophenyl, 2-fluorobenzyl, 2,4,6-trichlorophenyl,
- R 1 is haloalkenyl of 2 to 6 carbon atoms and 1 to 3 halogen atoms or halobenzyl of 1 to 3 halogen atoms.
- R 1 is haloallyl, especially, 3-trans-chloroallyl or monohalobenzyl, especially 4-chlorobenzyl.
- R 2 and R 3 groups are hydrogen, methyl, ethyl, propyl, methylthio, ethylthio, n-butylthio, methylthiomethyl, ethylthiomethyl, propylthiopropyl, ethylthiohexyl.
- R 2 and R 3 are alkyl of 1 to 3 carbon atoms or one of R 2 or R 3 is hydrogen and the other is alkylthioalkyl. Most preferably R 2 and R 3 are both methyl or one of R 2 or R 3 is hydrogen and the other is 2-ethylthiopropyl.
- R 4 groups are hydrogen, carbomethoxy, carboethoxy, carbopropoxy. Preferably R 4 is hydrogen.
- R 5 groups are hydrogen, NH 4 +, Na + , K + , Ca ++ , acetyl, propionyl, butyryl, isobutyryl, isovaleryl, 3,3-dimethylbutyryl, benzoyl, 1-naphthoyl, 2-naphthoyl.
- R 5 is hydrogen.
- Reaction (1) above may be performed at ambient temperature employing substantially equimolar amounts of the dione (II) and acid halide (IIa).
- the acid chloride (X ⁇ Cl) is used.
- the reaction may be conducted in an organic solvent, such as, halogenated hydrocarbons, ethers or glycols.
- a base be present, such as an organic amine or alkali metal carbonate salt, in order to quench the hydrogen halide which is evolved.
- Preferred organic amines are pyridine and trialkylamines such as triethylamine. Pressure conditions are not critical and atmospheric pressure may be conveniently employed.
- Reaction (2) may be performed in an inert organic solvent, such as, halogenated hydrocarbons or ethers. At least two moles of aluminum chloride per mole of ester (III) is used. Upon work-up, the crude product must be quenched with a proton-donor, preferably a mineral acid such as hydrochloric acid, to produce the trione (IIIa).
- a proton-donor preferably a mineral acid such as hydrochloric acid
- Reaction (3) is a conventional oxime forming condensation. Since the hydrochloride salt (IV) is employed, it is first neutralized with a base, preferably an alkali metal alkoxide, before combining with the trione (IIIa) or the tree base from Reaction 5 can be used directly.
- the reaction may be performed in an inert organic solvent, preferably lower alcohols.
- Reaction (4) is a conventional alkylation and may be performed in inert organic solvents such as dimethylsulfoxide, acetonitrile, ethers, glycol ethers or hydrocarbons.
- the reaction is performed in presence of a base, such as potassium carbonate at ambient temperature.
- Reaction (5) may be performed at elevated temperatures, preferably 30°-100° C.
- the phthalimide (VI) is preferably heated at atmospheric pressure with slight molar excess of hydrazine in an inert organic solvent, such as a lower alcohol, to reflux temperature.
- the crude mixture is then cooled and optionally quenched with a mineral acid, preferably hydrochloric acid, yielding the product salt (IV) or the tree base can be used directly in Reaction 3.
- a mineral acid preferably hydrochloric acid
- the trione (IIIa) may be formed in one step by treating the dione (II) with the acid halide (IIa) in a halogenated hydrocarbon solvent, preferably carbon tetrachloride, in the presence of trifluoromethyl sulfonic acid.
- a halogenated hydrocarbon solvent preferably carbon tetrachloride
- the reaction is performed at elevated temperature (30°-150° C.) and is complete within 90 hours but yields a mixture of products. Since the combined reaction time of reactions (1) and (2) is about 24 hours, and results in a purer product, the two-step sequence of reactions (1) and (2) is preferred to the one-step alternative.
- the starting materials of Formula II can be prepared by known procedures or obvious modification thereof (e.g. substitution of appropriate starting material).
- the compounds of Formula II can be conveniently prepared by the following process schematically represented by the following overall reaction equations ##STR6## wherein R 4' is alkyl of 1 through 3 carbon atoms and R 2 and R 3 are as defined hereinabove.
- the first reaction step is typically conducted by contacting compound A with compound B and a base (e.g. alkali metal alkoxides) under reactive conditions preferably in an inert solvent (e.g. alkanol, e.g. ethanol).
- a base e.g. alkali metal alkoxides
- an inert solvent e.g. alkanol, e.g. ethanol
- the reaction is conducted at about from 60° to 110° C. using about from 0.5 to 1.5 moles, preferably 0.9 to 1.1 moles, of compound A and of the base per mole of compound B.
- ester moiety of compound IIa is base hydrolyzed to the carboxylic acid, for example, by contacting metallic sodium in alkanol (e.g. ethanol) or alkali metal hydrogen at temperatures in the range of from about 60° to 110° C.
- compound C can be decarboxylated via treatment with a strong inorganic acid (e.g. hydrochloric acid, sulfuric acid).
- a strong inorganic acid e.g. hydrochloric acid, sulfuric acid.
- This step is typically conducted at temperatures in the range of 25° to 110° C. and can be conveniently conducted in situ after completion of the base hydrolyzation, Step 2.
- the compounds of Formula IIIa can also be prepared by reacting the compounds of Formula II with the corresponding anhydride in the presence of an organic base, preferably in an excess of anhydride or inert organic solvent. Typically, this reaction is conducted at temperatures in the range of about from 50° to 110° C. using about from 5 to 0.5 moles of anhydride per mole of compound II.
- oxyaminoalkylidene and “oxyiminoalkyl” refer to the radical having the formula ##STR7## wherein R is alkyl.
- R is alkyl.
- 1-allyloxyaminobutylidene and “1-allyloxyiminobutyl” refer to the radical having the formula ##STR8##
- step C The product from step C (21.2 g), absolute ethanol (650 ml) and hydrazine (3.7 g) were stirred in a flask and gradually heated to reflux. After 2 hours the mixture was cooled to room temperature, added to concentrated HCl (12.5 ml), then cooled to 0°. The precipitate was collected and washed with cold ethanol and water. The washings were concentrated to yield 21.5 of the crude product. This product was slurried with 50 ml methanol and the white solid was filtered and dried to yield 3.3 g of the crystalline product. The combined washings and filtrates were concentrated, and recrystallized (50 ml acetonitrile, 50 ml ether) to yield an additional 5.5 g of white crystalline product, 3-chloroallyloxyamine hydrochloride.
- step E To a solution of sodium methoxide (460 mg) in methanol (10 ml) was added the product of step D (1.22 g) and the suspension was stirred at room temperature for 15 minutes. To this suspension was added a solution of 2-butyro-5,5-dimethyl-cyclohexane-1,3-dione (see step B above) in 10 ml methanol. After stirring for two days at room temperature, the solution was concentrated in vacuo. The residue was taken up in 30 ml ethyl acetate and 25 ml 10% NaOH, whereupon three layers formed. The bottom two layers were collected, cooled, acidified with con. HCl (pH 1) and extracted twice with 30 ml methylene chloride.
- Example 2A (19.62 g) and aluminum chloride (26.67 g) were treated according to the procedure of Example 1B to yield 17.9 g. 2-propiono-5,5-dimethyl-cyclohexane-1,3-dione.
- Example 1D The product made according to Example 1D (1.22 g) and the product from Example 2B (1.65 g) were treated according to the procedure of Example 1E to yield the liquid product, 2-[1-(3'-chloroallyloxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione. See Compound No. 2 in Table A.
- the 2% sodium hydroxide solution extract was acidified to about pH 1 with aqueous 6 N hydrochloric acid and then extracted with 100 ml of methylene chloride. The organic layer was washed with 40 ml of water, dried over magnesium sulfate and then evaporated affording the trans isomer of the title compound as the residue (Compound No. 54 of Table A hereinbelow). The major portion of the title compound was recovered from the sodium hydroxide extract.
- This example illustrates the preparation of the acyloxy compounds of the invention.
- This example illustrates the preparation of the salts of the present invention.
- the compounds of the present invention are, in general, herbicidal in both pre- and post-emergent applications.
- the herbicidal compounds will be applied in herbicidally effective amounts to the locus or growth medium of the vegetation, e.g., soil infested with seeds and/or seedlings of such vegetation. Such application will inhibit the growth of or kill the seeds, germinating seeds and seedlings.
- the herbicidal compounds will be applied directly to the foliage and other plant parts.
- the herbicidal compounds of the invention are especially effective against grassy weeds and by proper dosage regulation can be safely applied for the control or prevention of grasses in broad leaf crops.
- the compounds when applied to growing plants above the ground in such an amount that the compounds will not kill beneficial plants, also show efficient plant growth regulating or retarding effects and may be advantageously employed, for example, to prevent or retard the growth of lateral buds in plants and to promote the thinning out of superfluous fruits in various fruit trees.
- the compounds can be applied in any of a variety of compositions.
- the compounds can be extended with a carrier material of the kind used and commonly referred to in the art such as inert solids, water and organic liquids.
- the compounds will be included in such compositions in sufficient amount so that they can exert an herbicidal or growth-regulating effect. Usually from about 0.5 to 95% by weight of the compounds are included in such formulations.
- Solid compositions can be made with inert powders.
- the compositions thus can be homogeneous powders that can be used as such, diluted with inert solids to form dusts, or suspended in a suitable liquid medium for spray application.
- the powders usually comprise the active ingredient admixed with minor amounts of conditioning agent.
- Natural clays either absorptive, such as attapulgite, or relatively non-absorptive, such as china clays, diatomaceous earth, synthetic fine silica, calcium silicate and other inert solid carriers of the kind conventionally employed in powdered herbicidal compositions can be used.
- the active ingredient usually makes up from 0.5-90% of these powder compositions.
- the solids ordinarily should be very finely divided. For conversion of the powders to dusts, talc, pyrophyllite, and the like, are customarily used.
- Liquid compositions including the active compounds described above can be prepared by admixing the compound with a suitable liquid diluent medium.
- suitable liquid diluent medium commonly employed are methanol, benzene, toluene, and the like.
- the active ingredient usually makes up about 0.5 to 50% of these liquid compositions. Some of these compositions are designated to be used as such, and others to be extended with large quantities of water.
- compositions in the form of wettable powders or liquids can also include one or more surface-active agents, such as wetting, dispersing or emulsifying agents.
- the surface-active agents cause the compositions of wettable powders or liquids to disperse or emulsify easily in water to give aqueous sprays.
- the surface-active agents employed can be of the anionic, cationic or nonionic type. They include, for example, sodium long-chain carboxylates, alkyl aryl sulfonates, sodium lauryl sulfate, polyethylene oxides, lignin sulfonates and other surface-active agents.
- a fertilizer When used as a pre-emergent treatment, it is desirable to include a fertilizer, an insecticide, a fungicide or another herbicide.
- the amount of active compound or composition administered will vary with the particular plant part or plant growth medium which is to be contacted, the general location of application--i.e., sheltered areas such as greenhouses, as compared to exposed areas such as fields--as well as the desired type of control.
- the compounds of the invention are applied at rates of 0.2 to 60 kg/ha, and the preferred rate is in the range of 0.5 to 40 kg/ha.
- the application rates for plant growth regulating or retarding activity will generally be lower than the rate used for killing the plants.
- such rates vary from 0.1 to 5 kg/ha, and preferably from 0.1 to 3 kg/ha.
- An acetone solution of the test compound was prepared by mixing 500 mg of the compound, 158 mg of a nonionic surfactant and 20 ml of acetone. Twenty ml of this solution was added to 80 ml of water to give the test solution.
- Seeds of the test vegetation were planted in a pot of soil and the test solution was sprayed uniformly onto the soil surface at a dose of 27.5 micrograms/cm 2 .
- the pot was watered and placed in a greenhouse.
- the pot was watered intermittently and observed for seedling emergence, health of emerging seedlings, etc., for a 3-week period. At the end of this period, the herbicidal effectiveness of the compound was rated based on the physiological observations. A 0-to-100 scale was used, 0 representing no phytotoxicity, 100 representing complete kill. The results of these tests appear in Table I.
- the test compound was formulated in the same manner as described above for the pre-emergent test. This formulation was uniformly sprayed on 2 similar pots of 24-day-old plants (approximately 15 to 25 plants per pot) at a dose of 27.5 micrograms/cm 2 . After the plants had dried, they were placed in a greenhouse and then watered intermittently at their bases, as needed. The plants were observed periodically for phytotoxic effects and physiological and morphological responses to the treatment. After 3 weeks, the herbicidal effectiveness of the compound was rated based on these observations. A 0-to-100 scale was used, 0 representing no phytotoxicity and 100 representing complete kill. The results of these tests appear in Table I.
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Abstract
Description
TABLE A __________________________________________________________________________ Compounds of the Formula ##STR9## ANALYSIS mp C H N No. R R.sup.1 °C. Calc. Fd. Calc. Fd. Calc. Fd. __________________________________________________________________________ 1 C.sub.2 H.sub.5 CH.sub.2 CClCH.sub.2 Oil 58.44 59.33 7.05 7.43 4.90 5.06 2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CClCH.sub.2 Oil 60.09 59.41 7.40 7.61 4.67 4.70 3 CH.sub.3 CH.sub.2 CH.sub.2 Trans-CH.sub.2 CHCHCl Oil 60.09 62.13 7.40 7.80 4.67 4.88 4 C.sub.2 H.sub.5 Trans-CH.sub.2 CHCHCl Oil 58.84 58.69 7.05 7.22 4.90 5.06 5 CH.sub.3 CH.sub.2 CH.sub.2 ##STR10## Oil 65.23 66.29 6.91 7.36 4.00 4.05 6 C.sub.2 H.sub.5 ##STR11## Oil 64.37 64.56 6.6 6.81 4.17 4.17 7 CH.sub.3 CH.sub.2 CH.sub.2 ##STR12## Oil 65.23 65.16 6.91 7.18 4.00 3.61 8 C.sub.2 H.sub.5 ##STR13## Oil 64.37 63.93 6.60 6.74 41.7 3.81 9 CH.sub.3 CH.sub.2 CH.sub.2 ##STR14## Oil 68.45 71.78 7.26 7.88 4.20 4.67 10 C.sub.2 H.sub.5 ##STR15## Oil 67.69 68.19 6.98 7.70 4.39 4.60 11 CH.sub.3 CH.sub.2 CH.sub.2 ##STR16## Oil 68.45 68.83 7.26 7.92 4.20 4.25 12 C.sub.2 H.sub.5 ##STR17## Oil 67.69 67.88 6.98 7.26 4.39 4.41 13 CH.sub.3 CH.sub.2 CH.sub.2 ##STR18## Oil 65.23 66.84 6.91 7.4 4.00 4.34 14 C.sub.2 H.sub.5 ##STR19## Oil 64.37 65.45 6.60 6.99 4.17 4.33 15 CH.sub.3 CH.sub.2 CH.sub.2 ##STR20## 70-71 59.38 60.34 6.03 6.36 3.65 3.83 16 CH.sub.3 CH.sub.2 CH.sub.2 (cis)-CH.sub.2 CHCHCl Oil 60.09 62.05 7.40 8.31 4.67 4.9 17 CH.sub.3 (R.sup.2 = H, R.sup.3 = H) ##STR21## Oil 61.33 61.45 5.49 6.43 4.43 4.56 18 CH.sub.3 (R.sup.2 = H, R.sup.3 = H) ##STR22## 84.7 54.89 55.55 4.61 5.07 4.27 4.17 19 CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 CClCH.sub.2 Oil 61.23 61.25 7.71 8.36 4.46 4.16 20 CH.sub.3 CH.sub.2 CClCH.sub.2 Oil 57.76 57.11 6.68 6.96 5.15 4.98 21 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CClCHCl Oil 53.90 54.52 6.33 6.8 4.19 4.20 22 CH.sub.3 CH.sub.2 CClCHCl Oil 50.99 50.77 5.60 6.02 4.57 4.6 23 CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 CClCHCl Oil 55.18 54.16 6.66 7.06 4.02 3.99 24 C.sub.2 H.sub.5 CH.sub.2 CClCHCl Oil 52.51 52.58 5.98 4.97 4.37 4.37 25 CH.sub.3 (CH.sub.2).sub.3 ##STR23## Oil 69.15 69.23 7.54 7.93 4.03 4.15 26 (CH.sub.3).sub.2 CHCH.sub.2 ##STR24## Oil 69.15 69.43 7.54 7.89 4.03 4.04 27 CH.sub.3 (cis)-CH.sub.2 CHCHCl Oil 57.46 62.13 6.68 7.48 5.25 5.56 28 C.sub.2 H.sub.5 (cis)-CH.sub.2 CHCHCl Oil 58.84 56.29 7.05 6.93 4.90 4.71 29 (CH.sub.3).sub.2 CHCH.sub.2 (cis)-CH.sub.2 CHCHCl Oil 61.23 59.71 7.71 7.95 4.46 4.11 30 C.sub.2 H.sub.5 ##STR25## Oil 58.39 55.23 5.72 5.93 3.78 3.35 31 CH.sub.3 CH.sub.2 CH.sub.2 ##STR26## Oil 59.40 56.53 6.03 6.23 3.64 3.22 32 CH.sub.3 (CH.sub.2).sub.3 ##STR27## Oil 60.30 58.37 6.33 6.37 3.52 3.24 33 (CH.sub.3).sub.2 CHCH.sub.2 ##STR28## Oil 60.30 57.62 6.33 6.37 3.52 3.12 34 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CClCH.sub.2 Oil 57.06 54.85 6.76 6.83 3.91 4.66 35 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CHCClCH.sub.3 Oil 61.23 62.67 7.71 7.90 4.46 5.12 36 CH.sub.3 ##STR29## Oil 63.45 61.30 6.26 6.14 4.35 3.98 37 CH.sub.3 (trans)-CH.sub.2 CHCHCl Oil 57.46 59.93 6.78 7.01 5.02 5.57 38 CH.sub.3 CH.sub.2 CHCClCH.sub.3 Oil 58.84 57.69 7.05 7.55 4.90 5.57 39 CH.sub.3 ##STR30## 41-42 66.87 67.56 6.60 6.85 4.59 4.61 40 CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 CH.sub.2 Cl Oil 59.69 61.55 8.02 8.46 4.64 4.04 41 CH.sub.3 CH.sub.2 CH.sub.2 (cis)-CH.sub.2 CHCHCl Oil 57.06 58.38 6.76 7.05 3.91 4.76 42 C.sub.2 H.sub.5 ##STR31## 70-71 58.39 58.71 5.72 5.89 3.78 3.97 43 CH.sub.3 CH.sub.2 CH.sub.2 (cis)-CH.sub.2 CHCHCH.sub.2 Cl Oil 61.24 62.1 7.70 8.01 4.46 4.08 44 CH.sub.3 CH.sub.2 CH.sub.2 Cl Oil 55.49 55.88 6.98 7.02 5.39 4.18 45 C.sub.2 H.sub.5 CH.sub.2 CHCClCH.sub.3 Oil 60.10 59.96 7.40 7.57 4.67 4.67 46 C.sub.2 H.sub.5 (trans)-CH.sub.2 CHCHCH.sub.2 Cl Oil 60.10 60.21 7.40 7.71 4.67 3.74 47 CH.sub.3 CH.sub.2 CH.sub.2 ##STR32## Oil 69.54 70.26 7.88 7.98 4.05 4.47 48 CH.sub.3 CH.sub.2 CH.sub.2 ##STR33## Oil 70.17 68.52 8.13 8.36 3.90 3.48 49 C.sub.2 H.sub.5 ##STR34## 54-56 66.47 67.43 6.69 7.36 3.88 4.08 50 C.sub.2 H.sub.5 ##STR35## Oil 61.78 62.25 6.00 6.17 3.79 3.93 51 CH.sub.3 CH.sub.2 CH.sub.2 ##STR36## Oil 62.35 63.3 6.31 6.63 3.65 3.76 52 C.sub.2 H.sub.5 ##STR37## Oil 58.39 57.10 5.72 5.50 3.78 3.84 53 CH.sub.3 CH.sub.2 CH.sub.2 ##STR38## Oil 59.38 56.02 6.03 5.58 3.64 3.78 54 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CHCHCl(trans) Oil 57.82 57.03 7.55 7.42 3.76 3.72 ##STR39## 55 CH.sub.3 CH.sub.2 CH.sub.2 ##STR40## Oil 62.34 61.54 7.13 7.14 3.30 2.93 ##STR41## 56 C.sub.2 H.sub.5 ##STR42## Oil 62.42 61.82 6.40 6.60 8.09 8.04 A CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CHCH.sub.2 (See U.S. Pat. No. 4,011,256) 57 CH.sub.3 CH.sub.2 ##STR43## Oil 61.78 60.9 6.00 6.5 3.79 3.87 58 CH.sub.3 CH.sub.2 CH.sub.2 ##STR44## Oil 62.65 61.63 6.31 7.00 3.65 4.16 __________________________________________________________________________ *Compound has CO.sub.2 CH.sub.3 substituent at the 4poisition of cyclohexane ring
TABLE I ______________________________________ HERBICIDAL ACTIVITY Pre/Post % Control (27.5 gamma/cm.sup.2) No. L M P C W O ______________________________________ 1 0/0 0/0 0/0 100/75 100/100 50/93 2 0/50 20/55 30/35 100/60 100/98 90/68 3 30/25 10/20 35/20 100/100 100/100 100/100 4 40/10 23/25 35/0 100/100 100/100 100/100 5 0/35 40/55 45/45 98/50 100/68 55/15 6 40/40 60/58 43/63 65/25 80/40 30/0 7 0/45 0/55 0/28 100/70 100/100 100/100 8 0/25 0/65 0/40 100/75 100/100 85/100 9 0/55 0/65 0/50 100/20 100/88 55/30 10 0/45 0/45 0/30 98/35 100/83 48/23 11 20/40 0/35 0/23 100/53 100/100 100/100 12 15/23 0/30 0/13 100/60 100/100 68/100 13 0/23 0/73 0/0 98/35 98/80 75/88 14 0/13 0/60 0/0 95/33 100/88 65/78 15 0/0 0/0 0/0 95/40 100/95 65/53 16 0/40 0/60 0/20 100/90 100/100 73/100 17 0/45 0/30 0/0 0/0 0/0 0/0 18 0/25 10/35 10/23 0/0 0/0 0/0 19 0/55 0/68 0/30 45/23 93/58 35/10 20 30/0 0/0 0/0 65/70 98/100 35/20 21 0/55 0/88 0/28 100/45 100/98 60/88 22 20/23 0/60 0/23 55/25 100/98 35/0 23 0/38 0/98 0/28 55/10 100/70 30/10 24 30/35 0/75 0/23 100/28 100/95 55/38 25 25/40 0/88 0/30 45/20 33/0 33/0 26 0/30 0/55 0/0 85/20 95/80 53/100 27 0/0 0/0 0/0 98/65 100/100 40/80 28 20/28 10/-- 0/0 100/60 100/100 53/100 29 0/28 0/70 0/0 70/0 100/98 50/45 30 0/50 0/40 0/48 63/23 100/80 35/20 31 0/28 0/38 0/0 45/20 100/45 55/55 32 0/35 0/60 0/0 0/0 0/25 0/0 33 0/43 0/23 0/40 0/0 25/15 15/0 34 0/25 0/0 0/0 80/30 100/100 53/98 35 48/33 0/63 0/0 95/23 100/93 43/75 36 35/20 0/0 25/0 98/55 100/100 48/90 37 50/35 0/55 0/0 100/90 100/100 53/98 38 0/15 0/0 0/0 98/60 100/98 35/20 39 35/33 0/0 0/0 100/68 100/100 43/93 40 70/25 0/38 0/25 40/10 50/43 30/0 41 33/13 0/0 13/15 100/55 100/100 65/98 42 18/28 0/0 15/33 53/0 53/28 0/25 43 0/25 0/0 0/0 25/25 55/60 20/20 44 60/0 0/0 0/0 55/60 100/93 35/35 45 0/30 0/0 0/0 63/35 100/95 45/75 46 15/23 0/0 0/0 15/25 60/45 15/20 47 0/30 0/0 0/0 90/43 100/60 50/25 48 0/25 0/43 0/25 100/30 100/90 35/25 49 0/0 0/0 0/0 100/70 100/100 35/100 50 43/15 20/55 15/15 60/30 60/58 45/15 51 35/15 0/0 0/15 100/50 90/65 55/90 52 0/25 0/45 0/23 40/20 85/40 0/0 53 0/35 0/80 0/40 70/20 98/58 30/20 54 0/40 0/20 0/0 100/100 100/100 100/100 55 0/30 0/10 0/18 100/100 100/100 100/100 56 0/0 0/0 0/0 98/98 100/100 50/100 57 60/0 70/55 35/45 --/90 100/95 78/88 58 0/25 0/55 0/45 --/80 100/100 100/100 ______________________________________ L = Lambsquarter (Chenopodium album) M = Mustard (Brassica arvensis) P = Pigweed (Amaranthus retroflexus) C = Crabgrass (Digitaria sanguinalis) W = Watergrass (Echinochloa crusgalli) O = Wild Oats (A'venua fatua)
TABLE II __________________________________________________________________________ HERBICIDAL ACTIVITY Pre/Post % Control (rate in gamma/cm.sup.2) No. Rate Soybeans Rice L M P C W O __________________________________________________________________________ 1 11 0/0 99/82 37/0 0/25 0/3 97/52 100/100 80/65 4.4 0/0 73/3 0/0 0/0 0/0 93/7 100/99 80/7 1.8 0/0 27/0 0/0 0/0 0/0 52/0 99/95 28/0 0.7 0/0 5/0 0/0 0/0 0/0 23/0 55/7 0/0 2 27.5 --/25 --/55 --/50 --/55 --/35 --/60 --/98 --/68 4.4 0/-- 95/-- 0/-- 0/-- 0/-- 23/-- 55/-- 0/-- 1.8 0/-- 83/-- 0/-- 0/-- 0/-- 88/-- 100/-- 77/-- 0.7 0/-- 60/-- 0/-- 0/-- 0/-- 83/-- 100/-- 58/-- 3 4.4 0/10 100/95 0/0 0/0 0/0 93/75 100/100 95/99 1.8 0/0 92/88 0/0 0/0 0/0 82/27 100/100 90/93 0.7 0/0 73/60 0/0 0/0 0/0 53/20 100/97 62/52 0.28 0/0 27/7 0/0 0/0 0/0 22/0 100/95 33/23 4 4.4 0/0 100/100 0/0 0/0 0/0 98/100 100/100 95/99 1.8 0/0 100/98 0/0 0/0 0/0 98/100 100/100 87/95 0.7 0/0 97/95 0/0 0/0 0/0 82/83 100/95 58/-- 0.28 0/0 80/50 0/0 0/0 0/0 67/12 100/90 0/0 5 27.5 --/10 --/10 --/35 --/55 --/45 --/50 --/68 --/15 4.4 0/-- 12/-- 0/-- 0/-- 0/-- 25/-- 78/-- 20/-- 1.8 0/-- 0/-- 0/-- 0/-- 0/-- 7/-- 58/-- 0/-- 0.7 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 0.28 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 0/-- 6 27.5 20/20 48/13 40/40 60/58 43/63 65/25 80/40 30/0 7 4.4 0/1 100/96 0/0 0/0 0/0 77/0 100/100 90/100 1.8 0/3 92/60 0/0 0/0 0/0 57/0 100/98 78/97 0.7 0/0 90/0 0/0 0/0 0/0 8/0 85/92 67/85 0.28 0/0 30/0 0/0 0/0 0/0 0/0 25/40 15/7 8 4.4 0/4 100/96 20/0 0/0 0/0 87/7 100/98 95/76 1.8 0/0 83/57 0/0 0/0 0/0 13/0 87/95 7/32 0.7 0/0 18/12 0/0 0/0 0/0 0/0 22/73 0/0 0.28 0/0 0/0 0/0 0/0 0/0 0/0 7/0 0/0 11 4.4 2/0 97/72 0/0 0/0 0/0 57/0 100/100 48/100 1.8 0/0 40/30 0/0 0/0 0/0 0/0 63/95 15/68 0.7 0/0 0/0 0/0 0/0 0/0 0/0 20/73 0/7 0.28 0/-- 0/-- 0/0 0/0 0/0 0/-- 0/-- 0/-- 16 4.4 0/0 78/57 0/0 0/0 63/0 60/25 100/100 27/92 1.8 0/0 65/10 0/0 0/0 65/0 0/3 92/98 0/15 0.7 0/0 3/3 0/0 0/0 0/0 0/0 40/95 0/0 0.28 0/0 0/0 0/0 0/0 0/0 0/0 0/32 0/0 19 27.5 0/10 13/0 0/55 0/68 0/30 45/23 93/58 35/10 20 27.5 0/0 50/60 0/30 0/0 0/0 70/65 100/98 20/35 22 27.5 0/0 43/55 20/23 0/60 0/23 55/25 100/98 35/0 23 27.5 0/20 20/10 0/38 0/98 0/28 55/10 100/70 30/10 24 27.5 0/0 78/50 30/25 0/75 0/23 100/28 100/95 78/38 27 4.4 0/0 77/87 0/0 0/0 0/0 --/93 100/100 13/17 1.8 0/0 53/10 0/0 0/0 0/0 --23 43/93 0/0 0.7 0/0 0/0 0/0 0/0 0/0 --/0 0/13 0/0 28 27.5 --/0 --/? --/-- --/-- --/0 --/-- --/-- --/-- 4.4 0/-- 72/-- 0/-- 0/-- 0/-- --/-- 100/-- 47/-- 1.8 0/-- 53/-- 0/-- 0/-- 0/-- --/-- 92/-- 0/-- 0.7 0/-- 10/-- 0/-- 0/-- 0/-- --/-- 63/-- 0/-- 0.28 0/-- 0/-- 0/-- 0/-- 0-- --/-- 0/-- 0/-- 29 27.5 0/0 60/20 0/28 0/70 0/0 70/0 100/98 50/45 A 4.4 0/0 90/90 0/0 0/0 0/0 --/100 100/100 88/100 1.8 0/0 62/62 0/0 0/0 0/0 --/100 98/100 52/63 0.7 0/0 37/37 0/0 0/0 0/0 --/22 65/80 40/22 0.28 0/0 3/3 0/0 0/0 0/0 --/0 0/10 7/0 37 4.4 0/10 100/100 0/0 0/0 0/0 --/100 100/100 47/93 1.8 0/0 98/77 0/0 0/0 0/0 --/85 100/98 45/15 0.7 0/0 35/12 0/0 0/0 0/0 --/22 100/47 22/0 0.28 0/ 2/0 0/0 0/0 0/0 --/0 52/7 0/0 39 4.4 0/0 72/98 0/0 0/0 0/0 --/77 100/100 42/73 1.8 0/0 62/73 0/0 0/0 0/0 --/13 98/92 0/0 0.7 0/0 32/12 0/0 0/0 0/0 --/0 55/75 0/0 0.28 0/0 0/0 0/0 0/0 0/0 --/0 32/0 0/0 46 11 --/5 --/87 --/0 --/32 --/25 --/13 --/100 --/100 4.4 0/0 90/48 0/0 0/0 0/0 32/0 100/100 60/82 1.8 0/0 60/13 0/0 0/0 0/0 3/0 100/98 45/73 0.7 0/0 13/5 0/0 0/0 0/0 0/0 40/58 0/12 0.28 0/-- 8/-- 0/-- 0/-- 0/-- 0/-- 13/-- 0/-- 54 4.4 2/0 100/100 0/0 0/0 0/0 94/97 100/100 99/100 1.8 0/0 100/100 0/0 0/0 0/0 95/90 100/100 96/100 0.7 0/0 99/100 0/0 0/0 0/0 73/50 98/98 85/100 0.28 0/0 73/82 0/0 0/0 0/0 13/15 58/90 73/87 55 4.4 5/0 98/100 0/0 0/0 0/0 93/75 100/100 99/100 1.8 2/0 87/100 0/0 0/0 0/0 33/58 100/100 92/100 0.7 0/0 57/97 0/0 0/0 0/0 0/15 98/98 77/98 0.28 0/0 0/62 0/0 0/0 0/0 0/0 10/92 62/82 __________________________________________________________________________
Claims (28)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/771,086 USRE32489E (en) | 1980-11-25 | 1985-08-30 | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
CA000491901A CA1267296A (en) | 1985-08-30 | 1985-09-30 | 2-(1-(3-chloroallyloxyamino) alkylidene)-5- alkylthioalkylcyclohexane-1,3-dione herbicides |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21020680A | 1980-11-25 | 1980-11-25 | |
US40522882A | 1982-08-05 | 1982-08-05 | |
US06/771,086 USRE32489E (en) | 1980-11-25 | 1985-08-30 | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US40522882A Continuation-In-Part | 1980-11-25 | 1982-08-05 | |
US06/406,423 Reissue US4440566A (en) | 1981-11-13 | 1982-08-09 | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
Publications (1)
Publication Number | Publication Date |
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USRE32489E true USRE32489E (en) | 1987-09-01 |
Family
ID=27395459
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US06/771,086 Expired - Lifetime USRE32489E (en) | 1980-11-25 | 1985-08-30 | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
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US (1) | USRE32489E (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5108488A (en) * | 1989-07-21 | 1992-04-28 | Valent U.S.A. Corporation | Synergistic herbicidal composition |
US5276188A (en) * | 1990-11-27 | 1994-01-04 | Ici Australia Operations Proprietary Limited | Crystallization process |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US3943176A (en) * | 1972-12-29 | 1976-03-09 | The Dow Chemical Company | 2-(Sulfur-substituted)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-ones |
US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
US3989737A (en) * | 1973-12-24 | 1976-11-02 | Nippon Soda Company Limited | 2-Cyclohexene-1-one derivatives |
US4011256A (en) * | 1973-08-15 | 1977-03-08 | Nippon Soda Company Limited | Cyclohexane derivatives |
US4033754A (en) * | 1974-12-11 | 1977-07-05 | Nippon Soda Company Limited | Substituted cyclohexene esters |
US4249937A (en) * | 1977-05-23 | 1981-02-10 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
EP0046860A1 (en) * | 1980-09-02 | 1982-03-10 | BASF Aktiengesellschaft | Cyclohexane-1,3-dione derivatives |
US4422864A (en) * | 1981-05-29 | 1983-12-27 | Basf Aktiengesellschaft | Cyclohexanedione derivatives, their preparation and herbicides containing them |
US4515729A (en) * | 1980-06-12 | 1985-05-07 | Nippon Soda Company Limited | Cyclohexane derivatives |
-
1985
- 1985-08-30 US US06/771,086 patent/USRE32489E/en not_active Expired - Lifetime
Patent Citations (10)
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---|---|---|---|---|
US3943176A (en) * | 1972-12-29 | 1976-03-09 | The Dow Chemical Company | 2-(Sulfur-substituted)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-ones |
US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
US4011256A (en) * | 1973-08-15 | 1977-03-08 | Nippon Soda Company Limited | Cyclohexane derivatives |
US3989737A (en) * | 1973-12-24 | 1976-11-02 | Nippon Soda Company Limited | 2-Cyclohexene-1-one derivatives |
US4033754A (en) * | 1974-12-11 | 1977-07-05 | Nippon Soda Company Limited | Substituted cyclohexene esters |
US4249937A (en) * | 1977-05-23 | 1981-02-10 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
US4515729A (en) * | 1980-06-12 | 1985-05-07 | Nippon Soda Company Limited | Cyclohexane derivatives |
EP0046860A1 (en) * | 1980-09-02 | 1982-03-10 | BASF Aktiengesellschaft | Cyclohexane-1,3-dione derivatives |
US4568383A (en) * | 1980-09-02 | 1986-02-04 | Basf Aktiengesellschaft | Cyclohexane-1,3-dione derivatives |
US4422864A (en) * | 1981-05-29 | 1983-12-27 | Basf Aktiengesellschaft | Cyclohexanedione derivatives, their preparation and herbicides containing them |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5108488A (en) * | 1989-07-21 | 1992-04-28 | Valent U.S.A. Corporation | Synergistic herbicidal composition |
US5276188A (en) * | 1990-11-27 | 1994-01-04 | Ici Australia Operations Proprietary Limited | Crystallization process |
US5354889A (en) * | 1990-11-27 | 1994-10-11 | Ici Australia Operations Proprietary Limited | Crystallization process |
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