CA1212679A - Derives de substitution 1-methylene carbonyles de 3-aryloxy-4-phenyl-azet-2-one - Google Patents

Derives de substitution 1-methylene carbonyles de 3-aryloxy-4-phenyl-azet-2-one

Info

Publication number: CA1212679A
Authority: CA; Canada
Prior art keywords: carbon atoms; hydrogen; compound; growth; azet
Prior art date: 1980-02-11
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

Application number

CA000452168A

Other languages

English (en)

Inventor

Francis J. Freenor, Iii

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.)

1980-02-11

Filing date

1984-04-17

Publication date

1986-10-14

1984-04-17 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1986-10-14 Application granted granted Critical

1986-10-14 Publication of CA1212679A publication Critical patent/CA1212679A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 8
-1 chloro, bromo, fluoro, iodo Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000001105 regulatory effect Effects 0.000 claims description 6
230000012010 growth Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 3
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
239000005648 plant growth regulator Substances 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 17
239000000203 mixture Substances 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000008635 plant growth Effects 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000000979 retarding effect Effects 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
239000004480 active ingredient Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
GIUTUZDGHNZVIA-UHFFFAOYSA-N 2-(ethylamino)acetic acid;hydrochloride Chemical compound Cl.CCNCC(O)=O GIUTUZDGHNZVIA-UHFFFAOYSA-N 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
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 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
101000957333 Homo sapiens Muscleblind-like protein 3 Proteins 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
102100038751 Muscleblind-like protein 3 Human genes 0.000 description 1
244000236458 Panicum colonum Species 0.000 description 1
235000015225 Panicum colonum Nutrition 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
240000004922 Vigna radiata Species 0.000 description 1
235000010721 Vigna radiata var radiata Nutrition 0.000 description 1
235000011469 Vigna radiata var sublobata Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
BTBVAFGANPMVDN-UHFFFAOYSA-N ethyl 2-(2-oxo-3-phenoxy-4-phenylazet-1-yl)acetate Chemical compound C=1C=CC=CC=1C=1N(CC(=O)OCC)C(=O)C=1OC1=CC=CC=C1 BTBVAFGANPMVDN-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000012085 test solution Substances 0.000 description 1
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000452168A 1980-02-11 1984-04-17 Derives de substitution 1-methylene carbonyles de 3-aryloxy-4-phenyl-azet-2-one Expired CA1212679A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US12042880A	1980-02-11	1980-02-11

Publications (1)

Publication Number	Publication Date
CA1212679A true CA1212679A (fr)	1986-10-14

Family

ID=22390217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000452168A Expired CA1212679A (fr)	1980-02-11	1984-04-17	Derives de substitution 1-methylene carbonyles de 3-aryloxy-4-phenyl-azet-2-one

Country Status (1)

Country	Link
CA (1)	CA1212679A (fr)

1984
- 1984-04-17 CA CA000452168A patent/CA1212679A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-04-17	MKEX	Expiry

Publication	Publication Date	Title
KR920010518B1 (ko)	1992-12-04	2-[1-(3-클로로알릴옥시아미노)알킬리덴]-5-알킬티오알킬-사이클로헥산-1,3-디온 제초제의 제조방법
NZ200282A (en)	1985-08-30	Treating plants,parts of plants,seeds thereof or the locus thereof with certain nitroarylsulphones in order to stimulate flower formation
US4456467A (en)	1984-06-26	1-Methylene carbonyl derivatives of 3-aryloxy-4-phenyl-azet-2-one
US4259104A (en)	1981-03-31	Herbicidal and plant-growth-regulating 2-phenoxyalkyl-oxadiazoles
CA1212679A (fr)	1986-10-14	Derives de substitution 1-methylene carbonyles de 3-aryloxy-4-phenyl-azet-2-one
US3697589A (en)	1972-10-10	N-(4-carboxy-benzylidene)amines
US4298375A (en)	1981-11-03	2-Substituted-5-phenyl-4-thiazolecarboxylic acids and their derivatives as safening agents
US4447450A (en)	1984-05-08	2,2-Bis(haloalkenyl)-1-cyano-1-alkoxycarbonylethylene fungicides
US4326878A (en)	1982-04-27	Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3,5-dithiones
US4417050A (en)	1983-11-22	Fungicidal, herbicidal and plant growth-regulating pyrimidyl-containing ethers
US4244731A (en)	1981-01-13	Method for controlling the growth of plants
US4339461A (en)	1982-07-13	N-Substituted 3-nitro-benzylamines
US4334909A (en)	1982-06-15	N-(Alkoxymethyl)-2'-nitro-6'-substituted-2-haloacetanilides and their use as herbicides and plant growth regulants
WO1985004877A1 (fr)	1985-11-07	Derives 1-methylene carbonyle de 3-aryloxy-4-phenyl-azet-2-one
EP0009331B1 (fr)	1983-07-20	Imides dérivés des acides 2-oxo-3-benzothiazoline-acétique et butyrique, procédé pour leur préparation et leur utilisation comme herbicides et agents de régulation de la croissance des plantes
US4407806A (en)	1983-10-04	Fungicidal, herbicidal and plant growth regulating pyridyl-containing ethers
US4701205A (en)	1987-10-20	Chemical tobacco sucker control
US4149873A (en)	1979-04-17	Composition for the regulation of plant metabolism
US4357159A (en)	1982-11-02	Haloethylthienylsulphonates for the regulation of plant metabolism
US4456471A (en)	1984-06-26	Herbicidal N-haloacetyl-2-methyl-6-substituted methoxymethylanilines
JP2673175B2 (ja)	1997-11-05	ナフトキノン系化合物、それを含む殺ダニ剤およびダニ類を防除する方法
US4230711A (en)	1980-10-28	Fungicidal n-substituted 4,4-dialkyl homophthalimides
US3507963A (en)	1970-04-21	Compositions and methods for controlling fungi with n-benzylidene alkylamines
GB2063855A (en)	1981-06-10	Triazolidine derivatives and process for preparing the same
JPS6293204A (ja)	1987-04-28	非医療用殺菌剤及びその製造方法