CA2158981C - Pyridines autocollantes a substituant heterocyclique - Google Patents

Pyridines autocollantes a substituant heterocyclique Download PDF

Info

Publication number: CA2158981C
Authority: CA; Canada
Prior art keywords: yloxy; pyrazol; methyl; chloropyrid; trifluoromethylpyrazol
Prior art date: 1993-03-26
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

CA002158981A

Other languages

English (en)

Other versions

CA2158981A1 (fr

Inventor

Axel Kleemann

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.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

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.)

1993-03-26

Filing date

1994-03-25

Publication date

2006-06-13

1994-03-25 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1994-03-25 Priority claimed from PCT/EP1994/000969 external-priority patent/WO1994022833A1/fr

1994-10-13 Publication of CA2158981A1 publication Critical patent/CA2158981A1/fr

2006-06-13 Application granted granted Critical

2006-06-13 Publication of CA2158981C publication Critical patent/CA2158981C/fr

2014-03-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
150000003222 pyridines Chemical class 0.000 title claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 50
-1 2-chloro pyrid-4-yl Chemical group 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 2
230000008635 plant growth Effects 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 6
125000003396 thiol group Chemical class [H]S* 0.000 claims 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
VRACLOBILSNGIC-UHFFFAOYSA-N 1,3-dimethyl-5-(6-methylsulfanylpyridin-2-yl)oxypyrazole-4-carbaldehyde Chemical compound CSC1=CC=CC(OC=2N(N=C(C)C=2C=O)C)=N1 VRACLOBILSNGIC-UHFFFAOYSA-N 0.000 claims 1
UOQBXUXACYCPGJ-UHFFFAOYSA-N 1-[6-(6-methoxypyridin-2-yl)oxypyridin-2-yl]ethyl 3-[2-bromo-2-[4-(chloromethyl)-3-methoxyphenyl]ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC1=CC=CC(=N1)OC1=CC=CC(=N1)C(C)OC(=O)C1C(C1C=C(C1=CC(=C(C=C1)CCl)OC)Br)(C)C UOQBXUXACYCPGJ-UHFFFAOYSA-N 0.000 claims 1
NSVCYLATROWHJG-UHFFFAOYSA-N 2,6-bis[(1-methylimidazol-2-yl)sulfanyl]pyridine;dihydrochloride Chemical compound Cl.Cl.CN1C=CN=C1SC1=CC=CC(SC=2N(C=CN=2)C)=N1 NSVCYLATROWHJG-UHFFFAOYSA-N 0.000 claims 1
ZDDBCRDVANWNLT-UHFFFAOYSA-N 2,6-bis[(6-bromopyridin-2-yl)sulfanyl]pyridine Chemical compound BrC1=CC=CC(SC=2N=C(SC=3N=C(Br)C=CC=3)C=CC=2)=N1 ZDDBCRDVANWNLT-UHFFFAOYSA-N 0.000 claims 1
PXUNAIDRXQGFII-UHFFFAOYSA-N 2-(6-methoxypyridin-2-yl)sulfanyl-1,3-thiazole Chemical compound COC1=CC=CC(SC=2SC=CN=2)=N1 PXUNAIDRXQGFII-UHFFFAOYSA-N 0.000 claims 1
AHDUXCOSCVKGQJ-UHFFFAOYSA-N 2-methoxy-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine Chemical compound COC1=CC=CC(SC=2NN=CN=2)=N1 AHDUXCOSCVKGQJ-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
NHLLQHNKZSBKNV-UHFFFAOYSA-N tert-butyl 4-[[[1,3-dimethyl-5-(6-methylsulfanylpyridin-2-yl)oxypyrazol-4-yl]methylideneamino]oxymethyl]benzoate Chemical compound CC(C)(C)OC(C1=CC=C(C=C1)CON=CC=1C(=NN(C1OC1=NC(=CC=C1)SC)C)C)=O NHLLQHNKZSBKNV-UHFFFAOYSA-N 0.000 claims 1
239000003921 oil Substances 0.000 description 62
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 18
238000012360 testing method Methods 0.000 description 16
239000002689 soil Substances 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
241000196324 Embryophyta Species 0.000 description 10
238000001816 cooling Methods 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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239000007787 solid Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
150000003573 thiols Chemical class 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000000969 carrier Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
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239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000007921 spray Substances 0.000 description 4
OHBIPNNTWKNAGC-UHFFFAOYSA-N 2,6-dibromo-4-methylpyridine Chemical compound CC1=CC(Br)=NC(Br)=C1 OHBIPNNTWKNAGC-UHFFFAOYSA-N 0.000 description 3
FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910000323 aluminium silicate Inorganic materials 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
IREZYNKPQCIUME-UHFFFAOYSA-N 2,6-bis(phenylmethoxy)pyridine Chemical compound C=1C=CC=CC=1COC(N=1)=CC=CC=1OCC1=CC=CC=C1 IREZYNKPQCIUME-UHFFFAOYSA-N 0.000 description 2
WEMPEMXDSUATEK-UHFFFAOYSA-N 2-bromo-6-phenylmethoxypyridine Chemical compound BrC1=CC=CC(OCC=2C=CC=CC=2)=N1 WEMPEMXDSUATEK-UHFFFAOYSA-N 0.000 description 2
VBEHFOMFHUQAOW-UHFFFAOYSA-N 2-chloro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1 VBEHFOMFHUQAOW-UHFFFAOYSA-N 0.000 description 2
ABYCTYJDRLQBMT-UHFFFAOYSA-N 6-bromo-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(Br)=C1 ABYCTYJDRLQBMT-UHFFFAOYSA-N 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

CA002158981A 1993-03-26 1994-03-25 Pyridines autocollantes a substituant heterocyclique Expired - Fee Related CA2158981C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP93105006		1993-03-26
EP93105006.6		1993-03-26
PCT/EP1994/000969 WO1994022833A1 (fr)	1993-03-26	1994-03-25	Pyridines herbicides a substitution heterocyclique

Publications (2)

Publication Number	Publication Date
CA2158981A1 CA2158981A1 (fr)	1994-10-13
CA2158981C true CA2158981C (fr)	2006-06-13

Family

ID=36587338

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002158981A Expired - Fee Related CA2158981C (fr)	1993-03-26	1994-03-25	Pyridines autocollantes a substituant heterocyclique

Country Status (1)

Country	Link
CA (1)	CA2158981C (fr)

1994
- 1994-03-25 CA CA002158981A patent/CA2158981C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2158981A1 (fr)	1994-10-13

Legal Events

Date	Code	Title	Description
2001-03-26	EEER	Examination request
2012-03-26	MKLA	Lapsed

Publication	Publication Date	Title
EP0690846B1 (fr)	1998-01-07	Pyridines herbicides a substitution heterocyclique
US5374604A (en)	1994-12-20	Herbicidal 2,6-substituted pyridines
EP0488474B1 (fr)	2002-04-17	Dérivés herbicides de carboxamide
KR100187799B1 (ko)	1999-06-01	제초성 카르복사미드 유도체, 이의 제조 및 이를 포함하는 조성물
US4543413A (en)	1985-09-24	Sulphonyl derivatives of N-phenyl pyridineamines
CA1231710A (fr)	1988-01-19	Composes heterocycliques a proprietes fongicides, herbicides et regulatrices de croissance vegetale
EP0723960A1 (fr)	1996-07-31	Pyridines 2,6-disubstituées et pyrimidines 2,4-disubstituées comme herbicides
US5824624A (en)	1998-10-20	Herbicidal 2-(hectero)aryloxy-6-arypyridines and 2-aryl-4-(hetero)aryloxypyrimidines
EP0823431A1 (fr)	1998-02-11	Pyridines 2,6-disubstituées et pyrimidines 2,4-disubstituées comme herbicides
CA1160229A (fr)	1984-01-10	Derives du pyridyliminomethylbenzene
EP0434132B1 (fr)	1995-04-05	Dérivés d'acrylonitrile herbicides
US5851952A (en)	1998-12-22	Herbicidal thienyloxyazines
JPH05213882A (ja)	1993-08-24	除草性ピコリンアミド誘導体
CA2158981C (fr)	2006-06-13	Pyridines autocollantes a substituant heterocyclique
US5972842A (en)	1999-10-26	Herbicidal cyanopyridines
US4931452A (en)	1990-06-05	N-cyanomethyl-2-pyridinone insecticides
EP0036638A2 (fr)	1981-09-30	2-Sulfinyl et 2-sulfonyl pyridine N-oxydes à activité herbicide et régulatrice de la croissance des plantes
GB2124615A (en)	1984-02-22	Heterocyclic compounds having fungicidal, herbicidal and plant- growth regulating properties
US6008161A (en)	1999-12-28	Herbicidal 2-(hetero)aryloxy-6-arylpyridines and 2-aryl-4-(hetero) aryloxypyrimidines
US5922738A (en)	1999-07-13	Heteroarylpyridine herbicides
EP0820996A1 (fr)	1998-01-28	Cyanopyridines à activité herbicide
US5981437A (en)	1999-11-09	Herbicidal substituted pyridine compounds
US4692183A (en)	1987-09-08	Diphenoxymethylpyridines and compositions containing same having herbicidal properties
IL121492A (en)	2002-02-10	2,6-disubstituted pyrimidines and 2,4-disubstituted pyrimidines and herbicidal compositions containing them
PL141279B1 (en)	1987-07-31	Herbicide composition containing novel chloroacetanilides and method of obtaining novel chloracetanilides