CA1271644A - Herbicides de type 2-¬1(3-chloroalkyloxyamino) alkylidene|-5-alkylthioalkylcyclohexane-1,3-dione - Google Patents

Herbicides de type 2-¬1(3-chloroalkyloxyamino) alkylidene|-5-alkylthioalkylcyclohexane-1,3-dione

Info

Publication number: CA1271644A
Authority: CA; Canada
Prior art keywords: composition; compound; cyclohexane; effective amount; trans
Prior art date: 1985-08-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000516351A

Other languages

English (en)

Inventor

Tatao Luo

William Loh

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-08-23

Filing date

1986-08-20

Publication date

1990-07-17

1986-08-20 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1990-07-17 Application granted granted Critical

1990-07-17 Publication of CA1271644A publication Critical patent/CA1271644A/fr

2007-07-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title abstract description 8
125000001118 alkylidene group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 67
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 56
241000196324 Embryophyta Species 0.000 claims description 23
230000002363 herbicidal effect Effects 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
-1 2-methylthio-propyl Chemical group 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
239000003960 organic solvent Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
239000012141 concentrate Substances 0.000 claims description 7
244000025670 Eleusine indica Species 0.000 claims description 5
235000014716 Eleusine indica Nutrition 0.000 claims description 5
240000002439 Sorghum halepense Species 0.000 claims description 5
239000003995 emulsifying agent Substances 0.000 claims description 4
240000001592 Amaranthus caudatus Species 0.000 claims description 3
235000009328 Amaranthus caudatus Nutrition 0.000 claims description 3
244000052363 Cynodon dactylon Species 0.000 claims description 3
240000008042 Zea mays Species 0.000 claims description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
235000005822 corn Nutrition 0.000 claims description 3
235000014820 Galium aparine Nutrition 0.000 claims description 2
241000320639 Leptochloa Species 0.000 claims description 2
235000007189 Oryza longistaminata Nutrition 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
235000007164 Oryza sativa Nutrition 0.000 claims description 2
235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
241001141210 Urochloa platyphylla Species 0.000 claims description 2
244000025254 Cannabis sativa Species 0.000 claims 2
240000006394 Sorghum bicolor Species 0.000 claims 1
231100000674 Phytotoxicity Toxicity 0.000 abstract description 9
241000209504 Poaceae Species 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229940073584 methylene chloride Drugs 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
239000000243 solution Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
229960003390 magnesium sulfate Drugs 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
229960000443 hydrochloric acid Drugs 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
230000008569 process Effects 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
XGNHRRHYGMFKAQ-OWOJBTEDSA-N o-[(e)-3-chloroprop-2-enyl]hydroxylamine Chemical compound NOC\C=C\Cl XGNHRRHYGMFKAQ-OWOJBTEDSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
235000017898 Digitaria ciliaris Nutrition 0.000 description 3
235000005476 Digitaria cruciata Nutrition 0.000 description 3
235000006830 Digitaria didactyla Nutrition 0.000 description 3
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
230000008635 plant growth Effects 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RAPFWIVDXSMGAP-UHFFFAOYSA-N 3-methylbutanethial Chemical compound CC(C)CC=S RAPFWIVDXSMGAP-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
KAALADJXIZIEMA-UHFFFAOYSA-N methyl 2-(2-methylsulfanylpropyl)-4,6-dioxocyclohexane-1-carboxylate Chemical compound COC(=O)C1C(CC(CC1CC(C)SC)=O)=O KAALADJXIZIEMA-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
230000000885 phytotoxic effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Chemical class 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
239000012085 test solution Substances 0.000 description 2
239000002023 wood Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
KAANTNXREIRLCT-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)C)C1=CC=CC=C1 KAANTNXREIRLCT-UHFFFAOYSA-N 0.000 description 1
QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical compound OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
ZOMGDJFTAMOGOY-UHFFFAOYSA-N 2-(2-ethylsulfanylpropyl)cyclohexane-1,3-dione Chemical compound CCSC(C)CC1C(=O)CCCC1=O ZOMGDJFTAMOGOY-UHFFFAOYSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 1
FBNJCUVUAUBKEN-UHFFFAOYSA-N 5-(2-ethylsulfanylpropyl)-2-propylidenecyclohexane-1,3-dione Chemical compound C(CC)=C1C(CC(CC1=O)CC(C)SCC)=O FBNJCUVUAUBKEN-UHFFFAOYSA-N 0.000 description 1
WFSIIZLAVIWNND-UHFFFAOYSA-N 5-(2-methylsulfanylpropyl)cyclohexane-1,3-dione Chemical compound CSC(C)CC1CC(=O)CC(=O)C1 WFSIIZLAVIWNND-UHFFFAOYSA-N 0.000 description 1
SGZXCDLTQCJGOR-UHFFFAOYSA-N 5-(3-methylsulfanylpropyl)cyclohexane-1,3-dione Chemical compound CSCCCC1CC(CC(C1)=O)=O SGZXCDLTQCJGOR-UHFFFAOYSA-N 0.000 description 1
NMZPARRXIXDSLR-UHFFFAOYSA-N 6-methylsulfanylhept-3-en-2-one Chemical compound CSC(CC=CC(C)=O)C NMZPARRXIXDSLR-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
JWRDLGKWGFUHPZ-UHFFFAOYSA-N C(CC)=C1C(C=C(CC1CC(C)SC)O)=O Chemical compound C(CC)=C1C(C=C(CC1CC(C)SC)O)=O JWRDLGKWGFUHPZ-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
240000001505 Cyperus odoratus Species 0.000 description 1
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LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
240000003829 Sorghum propinquum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
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229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
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WNCYAPRTYDMSFP-UHFFFAOYSA-N calcium aluminosilicate Chemical compound [Al+3].[Al+3].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O WNCYAPRTYDMSFP-UHFFFAOYSA-N 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
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GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
108010052322 limitin Proteins 0.000 description 1
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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239000011550 stock solution Substances 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000516351A 1985-08-23 1986-08-20 Herbicides de type 2-¬1(3-chloroalkyloxyamino) alkylidene|-5-alkylthioalkylcyclohexane-1,3-dione Expired - Fee Related CA1271644A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US76830185A	1985-08-23	1985-08-23
US768,301		1985-08-23
US79867085A	1985-11-15	1985-11-15
US798,670		1985-11-15

Publications (1)

Publication Number	Publication Date
CA1271644A true CA1271644A (fr)	1990-07-17

Family

ID=27118040

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000516351A Expired - Fee Related CA1271644A (fr)	1985-08-23	1986-08-20	Herbicides de type 2-¬1(3-chloroalkyloxyamino) alkylidene\|-5-alkylthioalkylcyclohexane-1,3-dione

Country Status (14)

Country	Link
EP (1)	EP0236313A1 (fr)
KR (1)	KR920010518B1 (fr)
CN (2)	CN1021282C (fr)
AU (2)	AU586200B2 (fr)
BE (1)	BE903349A (fr)
CA (1)	CA1271644A (fr)
CH (2)	CH666890A5 (fr)
DE (1)	DE3627410A1 (fr)
FR (1)	FR2586416B1 (fr)
GB (2)	GB2188321B (fr)
NL (2)	NL193944C (fr)
NO (1)	NO162555C (fr)
SE (1)	SE458683B (fr)
WO (1)	WO1987001699A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1987001699A1 (fr) *	1985-08-23	1987-03-26	Chevron Research Company	Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione
ES2014493B3 (es) *	1986-04-24	1990-07-16	Ciba-Geigy Ag	Acil-ciclohexandionas y sus eteres de oximas con efecto herbicida y regulador del crecimiento de las plantas.
GB8722838D0 (en) *	1987-09-29	1987-11-04	Shell Int Research	Oximino ether compounds
JP2536075B2 (ja) *	1988-06-27	1996-09-18	住友化学工業株式会社	除草組成物
US5108488A (en) *	1989-07-21	1992-04-28	Valent U.S.A. Corporation	Synergistic herbicidal composition
US6300281B1 (en) *	2000-07-03	2001-10-09	Valent U.S.A. Corporation	Optically pure(−) clethodim, compositions and methods for controlling plant growth comprising the same
PL2321270T3 (pl)	2008-08-19	2016-09-30		Ulepszony sposób addycji tiolanów do alfa, beta-nienasyconych związków karbonylowych lub sulfonylowych
CN105418470B (zh) *	2015-11-17	2017-12-15	江苏长青农化股份有限公司	一种烯草酮的合成方法
CN106187841B (zh) *	2016-07-08	2018-01-30	山东润博生物科技有限公司	一种烯草酮的工业化制备方法
WO2020172219A1 (fr) *	2019-02-20	2020-08-27	Valent U.S.A. Llc	Compositions à base de cléthodime et leurs procédés d'utilisation
CN113024425B (zh) *	2019-12-24	2022-05-17	沈阳科创化学品有限公司	一种烯草酮的制备方法
CN112225682B (zh) *	2020-10-19	2022-02-25	中国科学院大连化学物理研究所	一种提高合成烯草酮反应速度的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4440566A (en) *	1982-08-05	1984-04-03	Chevron Research Company	Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones
AU556148B2 (en) *	1982-01-29	1986-10-23	Ici Australia Limited	Cyclohexane -1,3- dione derivatives
WO1987001699A1 (fr) *	1985-08-23	1987-03-26	Chevron Research Company	Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione

1985
- 1985-09-19 WO PCT/US1985/001786 patent/WO1987001699A1/fr not_active Ceased
- 1985-09-19 EP EP85904913A patent/EP0236313A1/fr active Pending
- 1985-09-19 KR KR1019860700645A patent/KR920010518B1/ko not_active Expired
- 1985-09-19 CH CH1974/87A patent/CH666890A5/de not_active IP Right Cessation
- 1985-09-19 AU AU49541/85A patent/AU586200B2/en not_active Expired
- 1985-09-19 NL NL8520309A patent/NL193944C/nl not_active IP Right Cessation
- 1985-09-19 GB GB8708127A patent/GB2188321B/en not_active Expired
- 1985-09-30 BE BE0/215661A patent/BE903349A/fr not_active IP Right Cessation
1986
- 1986-06-30 AU AU59380/86A patent/AU585999B2/en not_active Ceased
- 1986-07-22 NL NL8601900A patent/NL8601900A/nl not_active Application Discontinuation
- 1986-07-30 CN CN90107624A patent/CN1021282C/zh not_active Expired - Lifetime
- 1986-07-30 CN CN86105662A patent/CN1011782B/zh not_active Expired
- 1986-08-13 DE DE19863627410 patent/DE3627410A1/de not_active Withdrawn
- 1986-08-18 FR FR8611806A patent/FR2586416B1/fr not_active Expired
- 1986-08-19 CH CH3344/86A patent/CH667086A5/de not_active IP Right Cessation
- 1986-08-20 CA CA000516351A patent/CA1271644A/fr not_active Expired - Fee Related
- 1986-08-21 GB GB8620373A patent/GB2179352B/en not_active Expired
- 1986-09-15 SE SE8603868A patent/SE458683B/sv not_active IP Right Cessation
- 1986-09-18 NO NO86863733A patent/NO162555C/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU4954185A (en)	1987-04-07
AU586200B2 (en)	1989-07-06
CN1011782B (zh)	1991-02-27
NL8520309A (nl)	1985-09-19
CN86105662A (zh)	1987-04-08
DE3627410A1 (de)	1987-02-26
CH667086A5 (de)	1988-09-15
CN1021282C (zh)	1993-06-23
BE903349A (fr)	1986-04-01
CN1051285A (zh)	1991-05-15
EP0236313A1 (fr)	1987-09-16
GB2179352B (en)	1989-08-09
NO162555C (no)	1990-01-17
GB8708127D0 (en)	1987-05-13
KR920010518B1 (ko)	1992-12-04
GB2188321B (en)	1989-08-31
NO162555B (no)	1989-10-09
GB8620373D0 (en)	1986-10-01
CH666890A5 (de)	1988-08-31
SE8603868D0 (sv)	1986-09-15
FR2586416B1 (fr)	1989-06-02
WO1987001699A1 (fr)	1987-03-26
NO863733D0 (no)	1986-09-18
SE458683B (sv)	1989-04-24
FR2586416A1 (fr)	1987-02-27
AU5938086A (en)	1987-02-26
NO863733L (no)	1987-03-26
GB2188321A (en)	1987-09-30
GB2179352A (en)	1987-03-04
KR870700287A (ko)	1987-12-28
NL193944C (nl)	2001-03-02
SE8603868L (sv)	1987-03-20
NL8601900A (nl)	1987-03-16
AU585999B2 (en)	1989-06-29
NL193944B (nl)	2000-11-01

Legal Events

Date	Code	Title	Description
1995-01-17	MKLA	Lapsed

Publication	Publication Date	Title
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
EP0239414B1 (fr)	1989-11-02	Amide N-benzylique de l'acide 2-(4-fluoro-3-trifluorométhylphénoxy)butanoique et composition herbicide le contenant
CA1271644A (fr)	1990-07-17	Herbicides de type 2-¬1(3-chloroalkyloxyamino) alkylidene\|-5-alkylthioalkylcyclohexane-1,3-dione
US4626276A (en)	1986-12-02	Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof
US3932458A (en)	1976-01-13	Antimicrobial and plant-active 4,5-dihalopyrrole-2-carbonitriles
GB2125042A (en)	1984-02-29	Herbicidal cyclohexane-1,3- diones
US4140520A (en)	1979-02-20	3,5-Dichloropyridyl-2-oxy-phenoxy malonic acids and derivatives and herbicidal use thereof
US4534785A (en)	1985-08-13	Herbicidal 5-deoxy-3-O-arylmethyl or substituted arylmethyl-1,2-O-ethylene-alpha-D-xylofuranose derivatives
US4701205A (en)	1987-10-20	Chemical tobacco sucker control
US4383849A (en)	1983-05-17	2,3-Dihydro-4-pyrone derivatives, their preparation the herbicidal compositions in which they are present and their use for selectively destroying weeds in crops
EP0002842A1 (fr)	1979-07-11	Dérivés de l'acide thiopropionique, compositions herbicides et/ou régulatrices de la croissance des plantes les contenant et méthodes pour contrôler la croissance des plantes indésirables
CA1267296A (fr)	1990-04-03	2-(1-(3-chloroallyloxyamino)-alcoylidene)-5- alcoylthioalcoylcyclohexane-1,3-diones, herbicides
US4859233A (en)	1989-08-22	2,3,6-trichlorobenzohydroxamic acid derivatives
US4012224A (en)	1977-03-15	Herbicidal use of β-aminoatroponitriles
US4824470A (en)	1989-04-25	2-(1-(5-Halothienylmethoxyimino)ethyl-3-hydroxy-5-(tetrahydro-2H-thiopyranyl)-cyclohex-2-en-1-one herbicides
US4339268A (en)	1982-07-13	Herbicidal nitroalkyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoates
US4456471A (en)	1984-06-26	Herbicidal N-haloacetyl-2-methyl-6-substituted methoxymethylanilines
NZ213582A (en)	1988-02-29	2-(3-chloroallyloxyamino)-alkylidene)-5-alkylthioalkyl cyclohexane-1,3-dione and herbicide composition
US4465502A (en)	1984-08-14	Herbicidal N-haloacetyl-2-substituted-6-acylanilines
EP0309271A1 (fr)	1989-03-29	Herbicides sélectifs, capables également de maîtriser la pousse des surgeons latéraux dans les plantes à tabac
US4052411A (en)	1977-10-04	Esters of derivatives of 2-imidazolidinylidenenitroacetic acid
AT398074B (de)	1994-09-26	Verfahren zur herstellung des neuen 2-(1-(3-trans-chlorallyoxyamino)-propyliden)-5- 2- ethylthiopropyl)-cyclohexan-1,3-dions
DE3546928C2 (de)	2003-04-30	Verwendung von Trans-2-[1-(3-chlorallyloxyamino)propyliden]-5-(2-ethylthiopropyl)cyclohexan-1,3-dion in herbiziden Mitteln
EP0025345A1 (fr)	1981-03-18	N-Cyanoalcoyl-haloacétamides, procédé pour leur préparation, utilisation comme antidotes d'herbicides et compositions comprenant ces composés
US4211551A (en)	1980-07-08	Herbicide