GB2090246A - Herbicidal substituted 2-[1- (oxyamino)-alkylidene]- cyclohexane-1,3-diones and derivatives - Google Patents

Herbicidal substituted 2-[1- (oxyamino)-alkylidene]- cyclohexane-1,3-diones and derivatives Download PDF

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GB2090246A
GB2090246A GB8135277A GB8135277A GB2090246A GB 2090246 A GB2090246 A GB 2090246A GB 8135277 A GB8135277 A GB 8135277A GB 8135277 A GB8135277 A GB 8135277A GB 2090246 A GB2090246 A GB 2090246A
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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

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  • Wood Science & Technology (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Herbicidally active compounds, particularly against grassy weeds, are represented by the general formula: <IMAGE> wherein R is alkyl or 1 to 6 carbon atoms or phenyl; R<1> is haloalkyl or 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 by 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; and R<5> is hydrogen, a cation, or <IMAGE> wherein R<6> is alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms. Preferably R, R<2> and R<3> are alkyl and R<4> and R<5> are hydrogen. The compounds may be used in both pre- and post-emergent applications.

Description

SPECIFICATION Herbicidal substituted 2-[1 -(oxyamino)-alkylidene]-cyclohexane-1 ,3-diones This invention relates to novel herbicidal compounds, compositions and method 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):
wherein R is alkyl of 1 to 6 carbon atoms or phenyl; R1 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 by 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; R2 and R3 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; R4 is hydrogen, or carbalkoxy of 2 to 4 carbon atoms; and R5 is hydrogen, a cation, or
wherein R6 is alky' of I to 6 carbon atoms or aryl of 6 to 10 carbon atoms.
A preferred class of compounds within the class defined by formula I is that wherein R4 and R5 are hydrogen, whilst a particularly preferred class is that wherein R4 and R5 are hydrogen and R, R2 and R3 are alkyl, i.e. the substituted 2-[1 -(oxyaminu)-alkylidene]-5,5-dialkylcyclohexane-1 3-diones.
Representative R groups are methyl, ethyl, propyl, isopropyl, n-butyl, isopentyl, neopentyl, n hexyl and phenyl.
Preferably 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.
Representative R1 groups are chloromethyl, bromethyl, fluoromethyl, 2-chloroethyl, 2-bromoethyl, 3,4-dichlorobutyl, 6-chlorohexyl, 3-cis-chloroallyl, 2,3-cis-dichloroallyl, 2-chloroallyl, 4,4-dichloro-but3-enyl, 4-bromo-3-bromomethyl-but-2-enyl, 5,5-dibromo-4-methyl-pent-2-enyl, 2,5-dichloro-hex-3enyl, p4luorophenyl, p4luorobenzyl, p-chlorobenzyl, p-bromophenyl, p-bromobenzyl, 3,4dichlorophenyl, 3,4-dichlorobenzyl, 2-fluorophenyl, 2-fluorobenzyi, 2,4,6-trichlorophenyl, 2,4,6trichlorobenzyl, 1 -bromo-naphth-2-yl, 2-chloronaphth-1 -yl, cyclopentyl, cyciohexyl, cycloheptyl, pmethylbenzyl, m-methylbenzyl, 2 ,4,6-triethylbenzyl, p-butylbenzyl, p-isopropylbenzyl, and p trifluoromethylbenzyl.
Preferably R1 is haloalkenyl of 2 to 6 carbon atoms and 1 to 3 halogen atoms or halobenzyl of 1 to 3 halogen atoms. Most preferably R1 is naloallyl, particularly, 3-cis-chioroallyl.
Repressntative R2 and R3 groups are hydrogen, methyl, ethyl, propyl, methylthio, ethylthio, nbutylthio, methylthiomethyl, ethylthiomethyl, propylthiopropyl, ethylthiohexyl.
Preferably R2 and R3 are alkyl of 1 to 3 carbon atoms. Most preferably R2 and R3 are both methyl.
Representative R4 groups are hydrogen, carbomethoxy, carboethoxy, carbopropoxy. Preferably R4 is hydrogen.
Representative R5 groups are hydrogen, NH4+, Na+, K+, Ca++, acetyl, propionyl, butyryl, isobutyryl, isovaleryl, 3,3-dimethylbutyryl, benzoyl, 1-naphthoyl, 2-naphthoyl. Preferably R5 is hydrogen.
The compounds of the invention may be prepared according to the following scheme:
The appropriate intermediates of the formula (IV) may be made according to the following reaction sequence:
1. Hydrazine H2NOR1 2. HC1 (fez) Compounds of the formula (I) wherein R5 is other than hydrogen may be prepared according to conventional procedures by treating the hydroxy compound (la) with an appropriate basic salt to yield compounds wherein R5 is Na+, No4+, Ca++, etc.Similarly, the hydroxy compound (la) may be acylated by treatment with an appropriate acid halide to yield compounds wherein R5 is
Reaction (1) above may be performed at ambient temperature employing substantially equimolar amounts of the dione (II) and acid halide (Ila). Preferably the acid chloride (X=CI) is used.The reaction may be conducted in an organic solvent, such as, halogenated hydrocarbons, ethers or glycols. It is preferred that 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 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 (Illa).
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 (Illa). 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 30-1 000C. The phthalimide (Vl) 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 quenched with a mineral acid, preferably hydrochloric acid, yielding the product salt (IV).
As an alternative to reactions (1) and (2) above the trione (Illa) may be formed in one step by treating the dione (II) with the acid halide (ill) in a halogenated hydrocarbon solvent, preferably carbon tetrachloride, in the presence of trifluoromethyl sulfonic acid. The reaction is performed at elevated temperature (30-1 500 C) and is compiete 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 respective products of the above reactions may be isolated and purified by conventional techniques such as chromatography, distillation, crystallization, etc., when appropriate.The products in the following Examples and Table A were identified by infrared and nmr spectroscopy and elemental analysis.
EXAMPLE 1 Preparation of 2-fl -j3'-chloroallyloxyamino)-butylidene]-5, ,3-dione A. Dimedone (5,5-dimethylcyclohexane-1 ,3-dione, 99%, 14.2 g), pyridine (9 ml) and methylene chloride (100 ml) were mixed in a fiask and butyryl chloride (11.4 g) was added dropwise. The mixture was stirred for 26 hours at room temperature and filtered. The filtrate was washed with HCI (6N, 100 ml), water (100 ml), saturated Na2COs (50 ml), water (50 ml), dried (MgS04). The solent was removed under reduced pressure to yield 3-butyroxy-5,5-dimethylcyclohex-2-ene-1-one as a yellow liquid.
B. To a dry flask containing methylene chloride (30 ml) and aluminum chloride (26.67 g) at ice bath temperature was added dropwise a solution of the product of step A (21.03 g) in dichloromethane (50 ml). The mixture was stirred for 2-1/2 hours then poured into 100 ml cold 6N HCI slowly with stirring. The mixture stood overnight. The organic phase was collected and washed with saturated Na2CO3 (100 ml) and water (100 mi). The solvent was stripped to yield 1 5.9 g yellow liquid. The Na2CO3 wash was acidified to pH2 with concentrated HCI, extracted with CH2CI2 and stripped to yield 4.8 g yellow liquid, identical to the composition of the 1 5.9 g of product. The combined products yielded 20.7 g 2-butyro-5,5-dimethylcyclohexane-1 ,3-dione.
C. To a solution of N-hydroxyphthalimide (33.6 g) in dimethylsulfoxide (200 ml) was added anhydrous potassium carbonate (28 g). After 10 minutes, 2,3-dichloropropene (20 ml) was added and the mixture was stirred at room temperature overnight. The mixture was poured into 1.2 liter ice-water and the resultant white precipitate was collected, washed with cold water (2 x 100 ml), air-dried and crystallized from 1.1 liter ethyl alcohol. Yield: 41.0 g. N-(3-chloroallyloxy)-phthalimide, white needles.
D. The product from step C (21.2 g), absolute ethanol (65O ml) and hydrazine (3.7 g) were stirred in a flack and gradually heated to reflux. After 2 hours the mixture was cooled to room temperature, added to concentrated HCI (12.5 ml), then cooled to 00. 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.
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. The methylene chloride extracts were combined, washed with water (2 x 20 ml), dried (MgS04) and concentrated in vacuo to yield the liquid product. 2-[1 -(3'-chloroallyloxyamino)- butylidene]-5,5-dimethylcyclohexane-1 ,3-dione. See compound No. 3 in Table A.
EXAMPLE 2 Preparation of 2-[1-(3'-chloroallyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-dione A. According to the procedure of Example 1 A, 5,5-dimethylcyclohexane-1 3-dione (14.2 g) and propionyl chloride (9.7 g) were reacted in pyridine (9 ml) and methylene chloride (100 ml) to yield 21.0 g. 3-propionoxy-5,5-dimethylcyclohex-2-en-l -lone.
B. The product of Example 2A (19.62 g) and aluminum chloride (26.67 g) were treated according to the procedure of Example 1 B to yield 17.9 g. 2-propiono-5,5-dimethyl-cyclohexane-1 ,3-dione.
C. The product made according to Example 1 D (1.22 g) and the product from Example 2B (1.65 g) were treated according to the procedure of Example 1 E to yield the liquid product 2-[1 -(3' chloroallyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1 ,3-dione. See Compound No. 4 in Table A.
UTILITY The compounds of the present invention are, in general, herbicidal in both pre- and post-emergent applications. For pre-emergent control of undesirable vegetation, 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 vegetaton. Such application will inhibit the growth of or kill the seeds, germinating seeds and seedlings. For post emergent applications, the herbicidal compounds will be applied directly to the foliage and other plant parts. Generally, the herbicidal compounds of the invention are particularly effective against grassy weeds. Some may be selective with respect to the type of application and/or type of weed.
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. In general, the compounds can be extended with a biologica!ly inert 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 reiatively non-absorptive, such as china clays, diatomaceous earth, synthetic fine silica, calcium silicate and other inert solid carriers of the kind conventionally empioyed in powdered herbididal compositions can be used. The active ingredient usually makes up from 0.590% 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. Typical of the liquid media 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 surfaceactive agent, 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-acjve agents employed can be of the anionic, cationic or nonionic type. They include, for example, sodium long-chain carboxylates, alkyl aryl sulfonates, sodium laury! sulfate, polyethylene oxides, lignin su'fon3tes and other suriace-active agents.
When used as a pre-emergent treatment, it is desirable to include a fertilizer, an insecticide, a fungicide or another herbicide.
The arnount 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. Generally for both pre- and post-emergent herbicidal 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 0.5 to 40 kg/ha. For plant growth regulating or retarding activity, it is essential to apply the compounds at a concentration not so high as to kill the plants. Therefore, the application rates for plant growth regulating or retarding activity will generally be lower than the rate used for killing the plants.Generally, such rates vary from 0.1 to 5 kg/ha, and preferably from 0.1 to 3 kg/ha.
Herbicidal tests on representative compounds of the invention were made using the following methods.
Pre-Emergent Herbicides Test 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/cm2. 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.
In follow-up tests, the procedure above was repeated using diluted test solution which was sprayed onto the soil surface at various dosages. The results of these tests appear in Table II.
Post-Emergent Herbicidal Test 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 1 5 to 25 plants per pot) at a dose of 27.5 micrograms/cm2. 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 O-to- 100 scale was used, 0 representing no phytotoxicity and 1CO representing complete kill. The results of these tests appear in Table I.
In follow-up tests, the procedure above was repeated using diluted test solution which was sprayed onto the soil surface at various dosages. The results of these tests appear in Table II.
TABLE A Compounds of the Formula
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
1 C2H5 CH2CCl=CH2 Oil 58.84 59.33 7.05 7.43 4.90 5.06 2 CH3CH2CH2 CH2CCl=CH2 Oil 60.09 59.41 7.40 7.61 4.67 4.70 3 CH3CH2CH2 Cis-CH2CH=CHCl Oil 60.09 62.13 7.40 7.80 4.67 4.88 4 C2H5 Cis-CH2CH=CHCl Oil 58.84 58.69 7.05 7.22 4.90 5.06 Cl 5 CH3CH2CH2 CH2-# Oil 65.23 66.29 6.91 7.36 4.00 4.05 Cl 6 C2H5 CH2-# Oil 64.37 64.56 6.6 6.81 4.17 4.17 7 CH3CH2CH2 CH2-#-Cl Oil 65.23 65.16 6.91 7.18 4.00 3.61 TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
8 C2H5 CH2-#Cl Oil 64.37 63.93 6.60 6.74 4.17 3.81 9 CH3CH2CH2 CH2-#-F Oil 68.45 68.83 7.26 7.92 4.20 4.25 10 C2H5 CH2-# Oil 67.69 68.19 6.98 7.70 4.39 4.60 F 11 CH3CH2CH2 CH2-#-F Oil 68.45 71.78 7.26 7.88 4.20 4.67 12 C2H5 CH2-#-F Oil 67.69 67.88 6.98 7.26 4.39 4.41 Cl 13 CH3CH2CH2 CH2-# Oil 65.23 66.84 6.91 7.4 4.00 4.34 TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
Cl 14 C2H5 CH2-# Oil 64.37 65.45 6.60 6.99 4.17 4.33 Cl 15 CH3CH2CH2 CH2-# 70-71 59.38 60.34 6.03 6.36 3.65 3.83 Cl 16 CH3CH2CH2 (trans)-CH2CH=CHCl Oil 60.09 62.05 7.40 8.31 4.67 4.9 Cl 17 CH3 CH2-# Oil 61.33 61.45 5.49 6.43 4.43 4.56 Cl 18 CH3 CH2-# 84.7 54.89 55.55 4.61 5.07 4.27 4.17 Cl 19 CH3(CH2)3 CH2CCl=CH2 Oil 61.23 61.25 7.71 8.36 4.46 4.16 20 CH3 CH2CCl=CH2 Oil 57.76 57.11 6.68 6.96 5.15 4.98 21 CH3CH2CH2 CH2CCl=CHCl Oil 53.90 54.52 6.33 6.8 4.19 4.20 22 CH3 CH2CCl=CHCl Oil 50.99 50.77 5.60 6.02 4.57 4.6 TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
23 CH3(CH2)3 CH2CCl=CHCl Oil 55.18 54.16 6.66 7.06 4.02 3.99 24 C2H5 CH2CCl=CHCl Oil 52.51 52.58 5.98 4.97 4.37 4.37 25 CH3(CH2)3 CH2-#-F Oil 69.15 69.23 7.54 7.93 4.03 4.15 26 (CH3)2CHCH2 CH2-#-F Oil 69.15 69.43 7.54 7.89 4.03 4.04 27 CH3 (trans)-CH2CH=CHCl Oil 57.46 62.13 6.68 7.48 5.15 5.56 28 C2H5 (trans)-CH2CH=CHCl Oil 58.84 56.29 7.05 6.93 4.90 4.71 29 (CH3)2CHCH2 (trans)-CH2CH=CHCl Oil 61.23 59.71 7.71 7.95 4.46 4.11 30 C2H5 CH2-#-Cl Oil 58.39 55.23 5.72 5.93 3.78 3.35 Cl 31 CH3CH2Ch2 CH2-#-Cl Oil 59.40 56.53 6.03 6.23 3.64 3.22 Cl TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
32 CH3(CH2)3 CH2-#-Cl Oil 60.30 58.37 6.33 6.37 3.52 3.24 Cl 33 (CH3)2CHCH2 CH2-#-Cl Oil 60.30 57.62 6.33 6.37 3.52 3.12 Cl 34 CH3CH2CH2 CH2CCl=CH2 Oil 57.06 54.85 6.76 6.83 3.91 4.66 35 CH3CH2CH2 CH2CH=CClCH3 Oil 61.23 62.67 7.71 7.90 4.46 5.12 36 CH3 CH2-#-Cl Oil 63.45 61.30 6.26 6.14 4.35 3.98 37 CH3 (cis)-CH2CH=CHCl Oil 57.46 59.93 6.78 7.01 5.02 5.57 38 CH3 CH2CH=CClCH3 OilOil 58.84 57.69 7.05.7.55 4.90 5.57 39 CH3 CH2-#-F 41-42 66.87 67.56 6.60 6.85 4.59 4.61 40 CH3(CH2)3 CH2CH2Cl Oil 59.69 61.65 8.02 8.46 4.64 4.04 41 CH3CH2CH2 (trans)-CH2CH=CHCl Oil 57.06 57.38 6.76 7.05 3.91 4.76 TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
Cl 42 C2H5 CH2-# 70-71 58.39 58.71 5.72 5.89 3.78 3.97 Cl 43 CH3CH2CH2 (trans)-CH2CH=CHCH2Cl Oil 61.24 62.1 7.70 8.01 4.46 4.08 44 CH3 CH4CH2Cl Oil 55.49 55.88 6.98 7.02 5.39 4.18 45 C2H5 CH2CH=CClCH3 Oil 60.10 59.96 7.40 7.57 4.67 4.67 46 C2H5 (cis)-CH2CH=CHCH2Cl Oil 60.10 60.21 7.40 7.71 4.67 3.74 47 C2H5 Ch2-#-F 54-60 66.47 67.43 6.69 7.26 3.88 4.08 48 C2H5 CH2-# Oil 61.78 62.55 6.00 6.17 3.79 3.93 CH3 49 CH3CH2CH2 CH2-# Oil 62.35 63.3 6.31 6.63 3.65 3.76 CH3 TABLE A (Continued)
ANALYSIS C H N No. R R mp C Calc. Fd. Calc. Fd. Calc. Fd.
50 C2H5 CH2-#-Cl Oil 58.39 57.10 5.72 5.50 3.78 3.84 Cl 51 CH3CH2CH2 CH2-#-Cl Oil 59.38 56.02 6.03 5.58 3.64 3.78 Cl A CH3CH2CH2 CH2CH=CH2 (See Patent No. 4,011,256) 52 CH3CH2 CH2-#-CF3 Oil 61.78 60.9 6.00 6.5 3.79 3.87 53 CH3CH2CH2 CH2-#-CF3 Oil 62.65 61.63 6.31 7.00 3.65 4.16 TABLE I - HERBICIDAL ACTIVITY Pre/Post % Control (27.5 gamma/cm2) No.L M P C W O 1 0/0 0/0 0/0 100/75 100/100 50/93 2 0/50 20/50 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 93/35 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/- ()/0 100/60 100/100 53/100 29 0i28 0/70 0/0 70/0 100/98 50/45 30 0/50 0/40 0/48 63/23 100/80 35/20 TABLE I (Cont'd) No.L M P C W O 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 0i43 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 OjO 0/0 100/68 100/100 43/93 40 70/2D 0/38 0/25 40/10 50/43 30/0 41 33/13 0/0 1 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 0/0 0/0 0/0 100/70 100/100 35/100 48 43/15 20/55 15/15 60/30 60/58 45/15 49 35/15 0/0 0/15 100/50 90/65 55/90 50 0/25 0/45 0/23 40/20 85/40 0/0 51 0/35 0/80 0/40 70/20 98/58 30/20 52 60/0 70/55 35/40 -/90 100/95 78/88 53 0/25 0/55 0/45 -/80 100/100 100/100 L = Lambsquarter (Chenopodium album) M = Mustard fBrassica arvensisj P = Pigweed tAmaranthus retroflexus) C = Crabgrass {Digitaria sanguinalisJ W = Watergrass hEchinochloa crusgalli) 0 = Wild Oats (Avenua fatua) TABLE II - HERBICIDAL ACTIVITY Pre/Post % Control (rate in gamma/cm2) 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 TABLE II (Cont'd) No.Rate Soybeans Rice L M P C W O 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 30/35 0/75 0/23 100/28 100/95 78/38 27 4.4 0/0 77/87 0/0 O/G 0/0 -/93 100/100 13/17 1.8 0/0 53j10 0/0 0/0 0/0 -23 43/93 0/0 0.7 0/0 0/0 0/0 0/0 O/C -/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/ TABLE (Cont'd) No.Rate Soybeans Rice L M P C W O 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/

Claims (11)

1. Compounds represented by the general formula:
wherein R is alkyl or 1 to 6 carbon atoms or phenyl; R' is haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, haloaryl of 6 to 10 carbon atoms, halobenzyl, ail of which contain 1 to 3 halogen atoms, cycloalkyl of 5 to 7 carbon atoms, or benzyl substituted by 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; R2 and R3 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; R4 is hydrogen, or carbalkoxy of 2 to 4 carbon atoms; and R5 is hydrogen, a cation, or
wherein R6 is alkyl of 1 to 6 carbon atoms or aryl or 6 to 10 carbon atoms.
2. Compounds as claimed in Claim 1, wherein R4 and R5 are hydrogen.
3. Compounds as claimed in Claim 1 or 2, wherein R is alkyl of 1 to 3 carbon atoms.
4. Compounds as claimed in Claim 1, 2 or 3, wherein R is haloalkenyl of 2 to 6 carbon atoms and 1 to 3 halogen atoms, or halobenzyl of 1 to 3 halogen atoms.
5. Compounds as claimed in Claim 1,2, 3 or 4, wherein R2 and R3 are alkyl of 1 to 3 carbon atoms.
6. 2-[1 -(3'-Chloroallyloxyamino)-butylidenej-5,5-dimethylcyclohexane-1 3-dione.
7.2-[1-(3t-Chloroallyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-dione.
8. A process for preparing a compound as claimed in Claim 1, wherein R5 is hydrogen, substantially as described in either of the foregoing Examples.
9. A herbicidal composition comprising a biologically inert carrier and a herbicidally effective amount of a compound as claimed in any one of Claims 1 to 7.
10. A method of killing vegetation which comprises applying to said vegetation or its growth environment a herbicidally effective amount of a compound as claimed in any one of Claims 1 to 7.
11. A method according to Claim 10, wherein the vegetation is crabgrass, watergrass or wild oats.
GB8135277A 1980-11-25 1981-11-23 Herbicidal substituted 2-(1-(oxyamino)-alkylidene-cyclohexane-1,3-diones and derivatives Expired GB2090246B (en)

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Cited By (9)

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US4650513A (en) * 1984-03-06 1987-03-17 Basf Aktiengesellschaft Cyclohexenones and their use for controlling undesirable plant growth
US4741768A (en) * 1985-11-15 1988-05-03 Chevron Research Company Herbicidal substituted 2-[1-(3-trans-chloro-allyloxyamino)alkylidene]-cyclohexane dione salts
US4945178A (en) * 1986-02-03 1990-07-31 Eastman Kodak Company Preparation of 4-carboalkoxy-1,3-cyclohexanedione type compounds
US5041613A (en) * 1989-08-28 1991-08-20 Eastman Kodak Company Organic compositions and their manufacture
US5225589A (en) * 1989-08-28 1993-07-06 Eastman Kodak Company Organic compositions and their manufacture
AU2001273157B2 (en) * 2000-07-03 2004-10-21 Sumitomo Chemical Company, Limited Optically pure(-) clethodim, compositions and methods for controlling plant growth comprising the same
US7060657B2 (en) 2002-07-18 2006-06-13 Bayer Cropscience Gmbh Combinations of cyclohexanedione oxime herbicides and safeners
EP2052605A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037632A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3227389A1 (en) * 1982-07-22 1984-01-26 Basf Ag, 6700 Ludwigshafen CYCLOHEXAN-1,3-DION DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND HERBICIDES THAT CONTAIN THESE COMPOUNDS
BE897413A (en) * 1982-08-09 1983-11-14 Chevron Res 2- [1- (OXVAMINO) -ALKYLIDENE] -5- (2-ETHYLTHIOPROPYL) -CYCLOHEXANE-1,3-DIONES SUBSTITUTED HERBICIDES
DE3482180D1 (en) * 1983-10-05 1990-06-13 Basf Ag CYCLOHEXENOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH.
US4640706A (en) * 1984-03-30 1987-02-03 Ciba-Geigy Corporation Cyclohexenonecarboxylic acid derivatives with herbicidal and plant growth regulating properties
US4626276A (en) * 1984-06-11 1986-12-02 Chevron Research Company Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof
AT398074B (en) * 1985-09-19 1994-09-26 Chevron Res Selective herbicide for crops of soya - is 2-chloro-allyloxy amino:propylidene 5-ethyl thio:propyl cyclohexane di:one
DE3546928C2 (en) * 1985-09-19 2003-04-30 Arysta Lifescience Corp Selective herbicide for crops of soya
TW221367B (en) * 1991-11-15 1994-03-01 Dunlena Pty Ltd
WO1994026696A1 (en) * 1993-05-11 1994-11-24 Dunlena Pty. Limited Herbicidal cyclohexanes

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US4011256A (en) * 1973-08-15 1977-03-08 Nippon Soda Company Limited Cyclohexane derivatives
US3950420A (en) * 1973-08-15 1976-04-13 Nippon Soda Company, Ltd. Cyclohexane derivatives
JPS577122B2 (en) * 1973-12-24 1982-02-09
IL48839A0 (en) * 1975-01-22 1976-03-31 Nippon Soda Co Novel cyclohexenyloxy-ester derivatives,their preparation and their use as herbicides

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650513A (en) * 1984-03-06 1987-03-17 Basf Aktiengesellschaft Cyclohexenones and their use for controlling undesirable plant growth
US4741768A (en) * 1985-11-15 1988-05-03 Chevron Research Company Herbicidal substituted 2-[1-(3-trans-chloro-allyloxyamino)alkylidene]-cyclohexane dione salts
US4945178A (en) * 1986-02-03 1990-07-31 Eastman Kodak Company Preparation of 4-carboalkoxy-1,3-cyclohexanedione type compounds
US5041613A (en) * 1989-08-28 1991-08-20 Eastman Kodak Company Organic compositions and their manufacture
US5225589A (en) * 1989-08-28 1993-07-06 Eastman Kodak Company Organic compositions and their manufacture
US5294733A (en) * 1989-08-28 1994-03-15 Eastman Kodak Company Organic compositions and their manufacture
US5359126A (en) * 1989-08-28 1994-10-25 Eastman Chemical Company Organic compositions and their manufacture
AU2001273157B2 (en) * 2000-07-03 2004-10-21 Sumitomo Chemical Company, Limited Optically pure(-) clethodim, compositions and methods for controlling plant growth comprising the same
US7060657B2 (en) 2002-07-18 2006-06-13 Bayer Cropscience Gmbh Combinations of cyclohexanedione oxime herbicides and safeners
EP2052605A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037632A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides

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