CA1133502A - Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers - Google Patents

Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers

Info

Publication number: CA1133502A
Authority: CA; Canada
Prior art keywords: compound; trifluoromethyl; atom; hydrogen atom; integer
Prior art date: 1979-04-02
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

CA324,622A

Other languages

English (en)

Inventor

Wayne O. Johnson

Colin Swithenbank

Roy Y. Yih

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas 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.)

1979-04-02

Filing date

1979-04-02

Publication date

1982-10-12

1979-04-02 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1979-04-02 Priority to CA324,622A priority Critical patent/CA1133502A/fr

1982-10-12 Application granted granted Critical

1982-10-12 Publication of CA1133502A publication Critical patent/CA1133502A/fr

Status Expired legal-status Critical Current

Links

-1 nitro diphenyl ethers Chemical class 0.000 title description 18
230000002363 herbicidal effect Effects 0.000 title description 16
150000002148 esters Chemical class 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
241000196324 Embryophyta Species 0.000 claims description 32
238000000034 method Methods 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000001963 growth medium Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract description 45
239000004009 herbicide Substances 0.000 abstract description 15
125000004429 atom Chemical group 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 26
150000003839 salts Chemical class 0.000 description 19
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 10
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239000003795 chemical substances by application Substances 0.000 description 7
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239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
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230000000885 phytotoxic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000010333 potassium nitrate Nutrition 0.000 description 2
239000004323 potassium nitrate Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000036647 reaction Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000004953 trihalomethyl group Chemical group 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
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YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 1
BFPMOCZPWJDBBY-UHFFFAOYSA-N 2-methoxyethyl 3-fluorobenzoate Chemical compound COCCOC(=O)C1=CC=CC(F)=C1 BFPMOCZPWJDBBY-UHFFFAOYSA-N 0.000 description 1
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230000001276 controlling effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
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238000010790 dilution Methods 0.000 description 1
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125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052806 inorganic carbonate Inorganic materials 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical class CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
229940073769 methyl oleate Drugs 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
150000004950 naphthalene Chemical class 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
239000010665 pine oil Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229940093932 potassium hydroxide Drugs 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

CA324,622A 1979-04-02 1979-04-02 Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers Expired CA1133502A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA324,622A CA1133502A (fr)	1979-04-02	1979-04-02	Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA324,622A CA1133502A (fr)	1979-04-02	1979-04-02	Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers

Publications (1)

Publication Number	Publication Date
CA1133502A true CA1133502A (fr)	1982-10-12

Family

ID=4113893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA324,622A Expired CA1133502A (fr)	1979-04-02	1979-04-02	Esters herbicides de 4-trifluoromethyl-3'- carboxy-4'-nitrodiphenylethers

Country Status (1)

Country	Link
CA (1)	CA1133502A (fr)

1979
- 1979-04-02 CA CA324,622A patent/CA1133502A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-10-12	MKEX	Expiry

Publication	Publication Date	Title
US3798276A (en)	1974-03-19	Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers
US4093446A (en)	1978-06-06	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US4039588A (en)	1977-08-02	Herbicidal 4-nitro-diphenyl ethers
US4070178A (en)	1978-01-24	Herbicidal diphenyl ethers
US3928416A (en)	1975-12-23	Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers
US4063929A (en)	1977-12-20	Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers
US4419124A (en)	1983-12-06	Herbicidal 4-trifluoromethyl-3'-nitrogen-substituted-4'-substituted diphenyl ethers
US4209318A (en)	1980-06-24	Herbicidal esters of 4-trifluoromethyl-3-carboxamido-4-nitro diphenyl ethers
US4076741A (en)	1978-02-28	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
CA1074335A (fr)	1980-03-25	4-trifluoromethyl-3'-cyanoalkoxy-4'-nitrodiphenylethers
CA1140563A (fr)	1983-02-01	Esters de 4-trifluoromethyl-3'-carboxy-4'- nitro-diphenylethers, a proprietes herbicides
GB1560416A (en)	1980-02-06	Trifluoromethylphenyl derivatives
US4515988A (en)	1985-05-07	Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers
US3954875A (en)	1976-05-04	Benzophenone herbicides
US4877897A (en)	1989-10-31	4-Trifluoromethyl-4'-nitrodiphenyl ethers
USRE31455E (en)	1983-12-06	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
CA1079303A (fr)	1980-06-10	4-trifluoromethyl1-4'-nitrodiphenylethers a proprietes herbicides
US3950379A (en)	1976-04-13	2-Cyano-diphenyl ethers
CA1309725C (fr)	1992-11-03	Oxydes 4-trifluoromethyl-4'-nitrobiphenyliques
US4306900A (en)	1981-12-22	Herbicidal nitrodiphenyl ethers
US4335249A (en)	1982-06-15	Herbicidal diphenyl ethers, sulfides, sulfoxides and sulfones
US4894479A (en)	1990-01-16	Herbicidal diphenyl ethers
CA1330445C (fr)	1994-06-28	Derives amide herbicides d'ethers 4-trifluoromethyl-3'-carboxyl-4'-nitrodipheniliques
USRE30361E (en)	1980-08-05	Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers
US4806682A (en)	1989-02-21	Sulfonium salts of diphenyl ethers