CA1160232A - Derives de pyridyliminomethylbenzene - Google Patents

Derives de pyridyliminomethylbenzene

Info

Publication number: CA1160232A
Authority: CA; Canada
Prior art keywords: compounds; compound according; alkoxy; alkyl; halo
Prior art date: 1979-03-13
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

CA000413867A

Other languages

English (en)

Inventor

Pieter. T. Haken

Shirley B. Webb

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 Canada Ltd

Original Assignee

Shell Canada Ltd

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.)

1979-03-13

Filing date

1982-10-20

Publication date

1984-01-10

1980-02-08 Priority claimed from CA000345301A external-priority patent/CA1160229A/fr

1982-10-20 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1982-10-20 Priority to CA000413867A priority Critical patent/CA1160232A/fr

1984-01-10 Application granted granted Critical

1984-01-10 Publication of CA1160232A publication Critical patent/CA1160232A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 58
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
125000005843 halogen group Chemical group 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
239000002253 acid Substances 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000004996 haloaryloxy group Chemical group 0.000 claims abstract description 5
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
-1 thionyl halide Chemical class 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
238000012360 testing method Methods 0.000 description 18
241000196324 Embryophyta Species 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
230000000855 fungicidal effect Effects 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
125000004414 alkyl thio group Chemical class 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
238000000034 method Methods 0.000 description 8
239000007921 spray Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000005507 spraying Methods 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000011149 active material Substances 0.000 description 5
239000007900 aqueous suspension Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241000233866 Fungi Species 0.000 description 4
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 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000003282 alkyl amino group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000005110 aryl thio group Chemical group 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
230000028070 sporulation Effects 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910000323 aluminium silicate Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000233622 Phytophthora infestans Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000005108 alkenylthio group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
125000005109 alkynylthio group Chemical group 0.000 description 2
125000004659 aryl alkyl thio group Chemical group 0.000 description 2
239000011575 calcium Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
125000005366 cycloalkylthio group Chemical group 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
208000013435 necrotic lesion Diseases 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241000123650 Botrytis cinerea Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
244000141359 Malus pumila Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Chemical group 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
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BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000012353 t test Methods 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
230000009974 thixotropic effect Effects 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

Landscapes

Pyridine Compounds (AREA)

CA000413867A 1979-03-13 1982-10-20 Derives de pyridyliminomethylbenzene Expired CA1160232A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000413867A CA1160232A (fr)	1979-03-13	1982-10-20	Derives de pyridyliminomethylbenzene

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7908822		1979-03-13
GB7908822		1979-03-13
CA000345301A CA1160229A (fr)	1979-03-13	1980-02-08	Derives du pyridyliminomethylbenzene
CA000413867A CA1160232A (fr)	1979-03-13	1982-10-20	Derives de pyridyliminomethylbenzene

Publications (1)

Publication Number	Publication Date
CA1160232A true CA1160232A (fr)	1984-01-10

Family

ID=27166580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000413867A Expired CA1160232A (fr)	1979-03-13	1982-10-20	Derives de pyridyliminomethylbenzene

Country Status (1)

Country	Link
CA (1)	CA1160232A (fr)

1982
- 1982-10-20 CA CA000413867A patent/CA1160232A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-01-10	MKEX	Expiry

Publication	Publication Date	Title
US4129573A (en)	1978-12-12	Compositions for and method of influencing plant growth and novel 1-phenyl-2-oxo-pyrrolidine-4-carboxylic acid derivatives
US4358446A (en)	1982-11-09	Use as fungicides of N-(3-pyridylmethyl)-N-acyl anilines
JPH08508277A (ja)	1996-09-03	除草性のヘテロ環式置換ピリジン
US4543413A (en)	1985-09-24	Sulphonyl derivatives of N-phenyl pyridineamines
US4066770A (en)	1978-01-03	3-Pyridylisoxazolidine fungicides
US4600712A (en)	1986-07-15	Fungicidally active compositions containing ethene derivatives
EP0015628B1 (fr)	1985-01-30	Utilisation comme fongicides de dérivés de pyridyliminométhylbenzène et leurs sels d'addition acides; dérivés de pyridyliminométhylbenzène et leurs sels d'addition acides; procédé pour leur préparation et intermédiaires utilisés dans le procédé; compositions fongicides contenant les composés
EP0013581B1 (fr)	1982-11-24	Dérivés du tétrahydrofuranne, un procédé pour leur préparation, compositions herbicides les contenant et leur utilisation dans une méthode pour maîtriser la croissance de plantes indésirables
US4833137A (en)	1989-05-23	Benzothiazinone derivatives
US4532329A (en)	1985-07-30	3-(R-thio)propionic acid substituted on adjacent carbon atoms by pyridyl and optionally-substituted phenyl, and corresponding optionally-substituted alkyl esters
EP0008145B1 (fr)	1984-02-01	Utilisation des dérivés de la phényliminométhylpyridine comme fongicides et régulateurs de croissance des plantes, compositions qui contiennent ces dérivés, de la phényliminométhylpyridine et leur préparation
EP0434132A2 (fr)	1991-06-26	Dérivés d'acrylonitrile herbicides
US4212868A (en)	1980-07-15	Certain fungicidal pyridinecarbaldehyde phenylhydrazones
US4404213A (en)	1983-09-13	Derivatives of certain pyridyliminomethyl-benzenes
EP0006254A1 (fr)	1980-01-09	Dérivés de benzoine oxime, leur procédé de préparation, compositions les contenant et leur méthode d'utilisation comme fongicides
EP0091148B1 (fr)	1987-11-19	Composés hétérocycliques fongicides
EP0152131B1 (fr)	1989-08-23	Dérivés de carboxamide, leur préparation et leur utilisation comme fongicides
US4355035A (en)	1982-10-19	Derivatives of certain pyridyliminomethylbenzenes
US4138402A (en)	1979-02-06	3-Pyrid-3-ylisoxazolidine fungicides
US5599818A (en)	1997-02-04	Fungicidal spiroheterocyclic compounds
US4163793A (en)	1979-08-07	Use of certain thiophenecarbaldehyde phenylhydrazones as fungicides
EP0621267A1 (fr)	1994-10-26	Dérivés de spiropipéridine et leur utilisation comme fongicides
GB1581675A (en)	1980-12-17	Fungicidal phenylhydrazones
EP0652215A1 (fr)	1995-05-10	Composés hétérocycliques substitués par un méthylène
US5508251A (en)	1996-04-16	Herbicidal methods and compositions comprising epoxy compounds