CA1078407A - M-isopropyl-phenylurees - Google Patents

M-isopropyl-phenylurees

Info

Publication number: CA1078407A
Authority: CA; Canada
Prior art keywords: propyl; compounds; phenylurea; compound; dimethyl
Prior art date: 1973-03-16
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

CA195,147A

Other languages

English (en)

Inventor

Richard J. Timmons

Gary B. Neyman

Lawrence S. Wittenbrook

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.)

ITT Inc

Original Assignee

ITT Industries Inc

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.)

1973-03-16

Filing date

1974-03-15

Publication date

1980-05-27

1974-03-15 Application filed by ITT Industries Inc filed Critical ITT Industries Inc

1980-05-27 Application granted granted Critical

1980-05-27 Publication of CA1078407A publication Critical patent/CA1078407A/fr

Status Expired legal-status Critical Current

Links

125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims abstract description 63
241000196324 Embryophyta Species 0.000 claims abstract description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 11
229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
150000002431 hydrogen Chemical class 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 46
238000000034 method Methods 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
IVLLJZFRQMSRRX-UHFFFAOYSA-N 1-isocyanato-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(N=C=O)=C1 IVLLJZFRQMSRRX-UHFFFAOYSA-N 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
CHZVEMPYOMWODS-UHFFFAOYSA-N 1-methoxy-1-methyl-3-(3-propan-2-ylphenyl)urea Chemical compound CON(C)C(=O)NC1=CC=CC(C(C)C)=C1 CHZVEMPYOMWODS-UHFFFAOYSA-N 0.000 claims 2
QWZWEJVCSVTACA-UHFFFAOYSA-N 1,1-dimethyl-3-(3-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC(NC(=O)N(C)C)=C1 QWZWEJVCSVTACA-UHFFFAOYSA-N 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 abstract description 17
239000000203 mixture Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
-1 1 Chemical class 0.000 description 14
238000009472 formulation Methods 0.000 description 13
230000000694 effects Effects 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000012948 isocyanate Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
235000013877 carbamide Nutrition 0.000 description 8
239000004009 herbicide Substances 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 8
239000007921 spray Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 5
108010081348 HRT1 protein Hairy Proteins 0.000 description 5
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 5
244000152045 Themeda triandra Species 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
244000025254 Cannabis sativa Species 0.000 description 4
241000209510 Liliopsida Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XCCNRBCNYGWTQX-UHFFFAOYSA-N 3-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(N)=C1 XCCNRBCNYGWTQX-UHFFFAOYSA-N 0.000 description 3
241000743339 Agrostis Species 0.000 description 3
244000237956 Amaranthus retroflexus Species 0.000 description 3
235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
244000292693 Poa annua Species 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
241001233957 eudicotyledons Species 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000010455 vermiculite Substances 0.000 description 3
235000019354 vermiculite Nutrition 0.000 description 3
229910052902 vermiculite Inorganic materials 0.000 description 3
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
235000017898 Digitaria ciliaris Nutrition 0.000 description 2
235000005476 Digitaria cruciata Nutrition 0.000 description 2
235000006830 Digitaria didactyla Nutrition 0.000 description 2
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
244000025670 Eleusine indica Species 0.000 description 2
235000014716 Eleusine indica Nutrition 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
241001520823 Zoysia Species 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
208000014674 injury Diseases 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
235000004135 Amaranthus viridis Nutrition 0.000 description 1
235000009344 Chenopodium album Nutrition 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
244000052363 Cynodon dactylon Species 0.000 description 1
241000508725 Elymus repens Species 0.000 description 1
241000234643 Festuca arundinacea Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241001562710 Muhlenbergia schreberi Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
241001668545 Pascopyrum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000404546 Soliva Species 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
238000013101 initial test Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
RHVNHKWMQOUSLJ-UHFFFAOYSA-N methoxymethanamine;hydrochloride Chemical compound Cl.COCN RHVNHKWMQOUSLJ-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000010451 perlite Substances 0.000 description 1
235000019362 perlite Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA195,147A 1973-03-16 1974-03-15 M-isopropyl-phenylurees Expired CA1078407A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US34188973A	1973-03-16	1973-03-16

Publications (1)

Publication Number	Publication Date
CA1078407A true CA1078407A (fr)	1980-05-27

Family

ID=23339443

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA195,147A Expired CA1078407A (fr)	1973-03-16	1974-03-15	M-isopropyl-phenylurees

Country Status (1)

Country	Link
CA (1)	CA1078407A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4579585A (en) *	1982-01-15	1986-04-01	Sandoz Ltd.	N'-[4-(1-Fluoromethyl-ethyl)phenyl]-urea derivatives

1974
- 1974-03-15 CA CA195,147A patent/CA1078407A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4579585A (en) *	1982-01-15	1986-04-01	Sandoz Ltd.	N'-[4-(1-Fluoromethyl-ethyl)phenyl]-urea derivatives

Legal Events

Date	Code	Title	Description
1997-05-27	MKEX	Expiry

Publication	Publication Date	Title
US4332961A (en)	1982-06-01	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
JPH0739400B2 (ja)	1995-05-01	トリアジン誘導体およびそれを有効成分とする除草剤
CA1133003A (fr)	1982-10-05	N-haloacetylphenylamino-carbonyl-oximes herbicides et regulateurs de la croissance vegetale
AU604472B2 (en)	1990-12-20	Insecticidal n'-substituted-n-alkylcarbonyl-n'-acyl hydrazines
US3907544A (en)	1975-09-23	Herbicidal 2-halo-N-(cyclicimidoalkylene)-substituted acetanilides
US3238222A (en)	1966-03-01	(n-3, 4-disubstituted phenyl-3 and/or omega methyl-2-pyrrolidinones and piperidones)
US4149874A (en)	1979-04-17	Substituted cyclopropylmethoxy anilides and their use as herbicides
CA1078407A (fr)	1980-05-27	M-isopropyl-phenylurees
EP0034012B1 (fr)	1984-09-12	Dérivés de la 2-nitro 5(phénoxy substitué) phénylalcanone-oxime et -imine utilisés comme herbicides
US3189431A (en)	1965-06-15	Method for the control of undesirable plant growth
US4874786A (en)	1989-10-17	Cyanoacetamido-derivatives having a fungicidal activity
US4423237A (en)	1983-12-27	Benzodioxane herbicides
US3988300A (en)	1976-10-26	Benzophenone ureas and method for utilizing the same
US3089765A (en)	1963-05-14	Herbicidal method
US4111682A (en)	1978-09-05	N-(aminoalkylene thiomethyl)-N'-(aryl) urea herbicides
KR910002672B1 (ko)	1991-05-03	페닐아세트아닐리드 유도체의 제조방법
US4758263A (en)	1988-07-19	2-(2,5-difluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5 diones
JP2650823B2 (ja)	1997-09-10	Ｎ−アリールオキシアシル−ｎ−フェニルテトラヒドロフタラミン酸誘導体およびその製造法ならびにそれを有効成分とする除草剤
US4026697A (en)	1977-05-31	Method for utilizing benzophenone ureas
US3867429A (en)	1975-02-18	Alkynyloxy)alkyl and (alkenyloxy)alkyl carbamates
US3836572A (en)	1974-09-17	Dicarbamoyl hydroxamates
US3445222A (en)	1969-05-20	Herbicidal compositions containing trisubstituted-phenyl n-methylcarbamates
CS208667B2 (en)	1981-09-15	Herbicide means and method of making the active substances
CA1104153A (fr)	1981-06-30	Traduction non-disponible
US4102673A (en)	1978-07-25	1-Phenyl-hexyl ureas as herbicides

CA1078407A - M-isopropyl-phenylurees - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=23339443

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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