CA1293507C - Pyridiazines fongicides - Google Patents

Pyridiazines fongicides

Info

Publication number: CA1293507C
Authority: CA; Canada
Prior art keywords: compound; methyl; chloro; hydrogen; mixture
Prior art date: 1986-06-12
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 - Lifetime

Application number

CA000511415A

Other languages

English (en)

Inventor

George William Johnson

Wendell Ray Arnold

William Clinton Dow

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.)

Eli Lilly and Co

Original Assignee

Eli Lilly and 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.)

1986-06-12

Filing date

1986-06-12

Publication date

1991-12-24

1986-06-12 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1986-06-12 Priority to CA000511415A priority Critical patent/CA1293507C/fr

1991-12-24 Application granted granted Critical

1991-12-24 Publication of CA1293507C publication Critical patent/CA1293507C/fr

2008-12-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000000855 fungicidal effect Effects 0.000 title claims description 14
150000004892 pyridazines Chemical class 0.000 title abstract description 6
241000233866 Fungi Species 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 144
150000001875 compounds Chemical class 0.000 claims description 140
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 32
-1 chloro, bromo, methyl Chemical group 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000001309 chloro group Chemical group Cl* 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
239000012990 dithiocarbamate Substances 0.000 claims description 18
238000009472 formulation Methods 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000001246 bromo group Chemical group Br* 0.000 claims description 12
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 12
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 11
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 11
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 9
239000000417 fungicide Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
230000002140 halogenating effect Effects 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002346 iodo group Chemical group I* 0.000 claims description 6
229910021645 metal ion Inorganic materials 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 5
RAQXMXAKHJIKEE-UHFFFAOYSA-N 3,6-dichloro-4-(1-chloro-2-methylpropan-2-yl)pyridazine Chemical compound ClCC(C)(C)C1=CC(Cl)=NN=C1Cl RAQXMXAKHJIKEE-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
238000006073 displacement reaction Methods 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 9
CJWXEEPLGDEHCW-UHFFFAOYSA-N 4-(1-bromo-2-methylpropan-2-yl)-3,6-dichloropyridazine Chemical compound BrCC(C)(C)C1=CC(Cl)=NN=C1Cl CJWXEEPLGDEHCW-UHFFFAOYSA-N 0.000 claims 1
231100001184 nonphytotoxic Toxicity 0.000 claims 1
230000000254 damaging effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
239000000047 product Substances 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 46
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000004094 surface-active agent Substances 0.000 description 31
239000000543 intermediate Substances 0.000 description 30
239000003921 oil Substances 0.000 description 28
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
239000007787 solid Substances 0.000 description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
238000002360 preparation method Methods 0.000 description 23
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
241000196324 Embryophyta Species 0.000 description 19
239000010410 layer Substances 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 18
239000012267 brine Substances 0.000 description 17
238000004128 high performance liquid chromatography Methods 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000002671 adjuvant Substances 0.000 description 15
238000005804 alkylation reaction Methods 0.000 description 15
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 15
VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 15
229910001870 ammonium persulfate Inorganic materials 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
230000029936 alkylation Effects 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 14
229910001961 silver nitrate Inorganic materials 0.000 description 14
239000002904 solvent Substances 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
239000002689 soil Substances 0.000 description 13
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000004495 emulsifiable concentrate Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 12
GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000002518 antifoaming agent Substances 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 10
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
229920001285 xanthan gum Polymers 0.000 description 10
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
229960005419 nitrogen Drugs 0.000 description 9
238000010992 reflux Methods 0.000 description 9
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 7
241000233622 Phytophthora infestans Species 0.000 description 7
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 7
150000004659 dithiocarbamates Chemical class 0.000 description 7
239000002736 nonionic surfactant Substances 0.000 description 7
239000007921 spray Substances 0.000 description 7
229940032330 sulfuric acid Drugs 0.000 description 7
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000004342 Benzoyl peroxide Substances 0.000 description 6
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
235000019400 benzoyl peroxide Nutrition 0.000 description 6
230000002209 hydrophobic effect Effects 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
239000002245 particle Substances 0.000 description 6
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 6
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 6
229920001732 Lignosulfonate Polymers 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000002411 adverse Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
239000003999 initiator Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 4
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000002301 combined effect Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000007858 starting material Substances 0.000 description 4
BGVTUIRPHLSMJU-UHFFFAOYSA-N 3,6-dimethylpyridazine Chemical compound CC1=CC=C(C)N=N1 BGVTUIRPHLSMJU-UHFFFAOYSA-N 0.000 description 3
PRORLQAJNJMGAR-UHFFFAOYSA-N 3-chloro-6-methylpyridazine Chemical compound CC1=CC=C(Cl)N=N1 PRORLQAJNJMGAR-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 3
239000005802 Mancozeb Substances 0.000 description 3
235000008098 Oxalis acetosella Nutrition 0.000 description 3
244000126309 Trifolium dubium Species 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910003460 diamond Inorganic materials 0.000 description 3
239000010432 diamond Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 3
229920000940 maneb Polymers 0.000 description 3
239000000463 material Substances 0.000 description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000001603 reducing effect Effects 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
VQAFMTSSCUETHA-UHFFFAOYSA-N 3,6-dibromopyridazine Chemical compound BrC1=CC=C(Br)N=N1 VQAFMTSSCUETHA-UHFFFAOYSA-N 0.000 description 2
RCZFXRMIHOUWJD-UHFFFAOYSA-N 3-(trichloromethyl)pyridazine Chemical class ClC(Cl)(Cl)C1=CC=CN=N1 RCZFXRMIHOUWJD-UHFFFAOYSA-N 0.000 description 2
QZWIXLPWMGHDDD-UHFFFAOYSA-N 3-methyl-1h-pyridazin-6-one Chemical compound CC1=CC=C(O)N=N1 QZWIXLPWMGHDDD-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
YMUOLGNUZURDEW-UHFFFAOYSA-N 6-chloropyridazine-3-carbonitrile Chemical compound ClC1=CC=C(C#N)N=N1 YMUOLGNUZURDEW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
241000233679 Peronosporaceae Species 0.000 description 2
241000471406 Physoderma maydis Species 0.000 description 2
241000233620 Phytophthora cryptogea Species 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
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PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
229910001447 ferric ion Inorganic materials 0.000 description 1
239000012025 fluorinating agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
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125000001475 halogen functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229940060367 inert ingredients Drugs 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000266 injurious effect Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
BSABBBMNWQWLLU-UHFFFAOYSA-N lactaldehyde Chemical compound CC(O)C=O BSABBBMNWQWLLU-UHFFFAOYSA-N 0.000 description 1
235000019357 lignosulphonate Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001437 manganese ion Inorganic materials 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
244000000003 plant pathogen Species 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
229950006800 prenderol Drugs 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000033458 reproduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
201000010153 skin papilloma Diseases 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1

Landscapes

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

CA000511415A 1986-06-12 1986-06-12 Pyridiazines fongicides Expired - Lifetime CA1293507C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000511415A CA1293507C (fr)	1986-06-12	1986-06-12	Pyridiazines fongicides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000511415A CA1293507C (fr)	1986-06-12	1986-06-12	Pyridiazines fongicides

Publications (1)

Publication Number	Publication Date
CA1293507C true CA1293507C (fr)	1991-12-24

Family

ID=4133333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000511415A Expired - Lifetime CA1293507C (fr)	1986-06-12	1986-06-12	Pyridiazines fongicides

Country Status (1)

Country	Link
CA (1)	CA1293507C (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114727595A (zh) *	2019-12-03	2022-07-08	阿西姆普托特有限公司	用于将容器绝缘的塞子以及冷却方法
CN119118927A (zh) *	2024-09-10	2024-12-13	上海毕得医药科技股份有限公司	一种3-氯-6-甲基哒嗪的合成方法

1986
- 1986-06-12 CA CA000511415A patent/CA1293507C/fr not_active Expired - Lifetime

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114727595A (zh) *	2019-12-03	2022-07-08	阿西姆普托特有限公司	用于将容器绝缘的塞子以及冷却方法
CN114727595B (zh) *	2019-12-03	2024-03-26	阿西姆普托特有限公司	用于将容器绝缘的塞子以及冷却方法
CN119118927A (zh) *	2024-09-10	2024-12-13	上海毕得医药科技股份有限公司	一种3-氯-6-甲基哒嗪的合成方法

Legal Events

Date	Code	Title	Description
1994-06-26	MKLA	Lapsed

Publication	Publication Date	Title
CA1331180C (fr)	1994-08-02	Les alkoxy-1,2,4-triazolo [1,5-c] pyrimidine-2-sulfonamides, procede pour leur preparation et composes intermediaires
AU730027B2 (en)	2001-02-22	Pesticidal 3-(substituted phenyl)-5-(thienyl or furyl)-1,2,4-triazoles
JP2990377B2 (ja)	1999-12-13	複素環式化合物
CA1340481C (fr)	1999-04-06	Herbicides a base de quinoxalinyloxyphenoxypropanoate d'alkylene heterocyclique
JPH02501309A (ja)	1990-05-10	複素環化合物
BR112014003587B1 (pt)	2021-04-13	Derivados de 5-flúor-4-imino-3-(substituído)-3,4-dihidropirimidin-2(1h)ona, composição e método para controle ou prevenção de um patógeno fúngico
KR20090038876A (ko)	2009-04-21	제초제 화합물로 유용한 피리도[2,3―ｂ] 피라진 유도체
US4824475A (en)	1989-04-25	Enhanced herbicidal triazine compositions and method of use
WO1991013065A1 (fr)	1991-09-05	Herbicides a base d'acide benzoique 6-aryl-2-substitue
CA1322759C (fr)	1993-10-05	Derives pyrazole, procede pour leur production, et fongicides agricoles et horticoles en contenant
CN101084224B (zh)	2013-12-04	具有杀真菌活性的噻吩并-嘧啶化合物
EP0208431B1 (fr)	1990-07-11	Pyridazines fongicides
KR910004206B1 (ko)	1991-06-24	4, 5, 6, 7-테트라히드로-2h-인다졸 유도체의 제조방법
JPH08301845A (ja)	1996-11-19	ある種の３−ベンゾイル−４−オキソラクタム
US4523947A (en)	1985-06-18	Use of triazine derivatives for protecting maize and sorghum plants
US4791110A (en)	1988-12-13	Fungicidal pyridazines
HU203084B (en)	1991-05-28	Herbicidal compositions comprising sulfonanilide derivatives as active ingredient and process for producing the active ingredient
CA2033040A1 (fr)	1991-06-28	Derives de substitution de la pyridine
CA2213078A1 (fr)	1996-08-22	Derives d'isoxazole
JPH07258223A (ja)	1995-10-09	４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
US4909829A (en)	1990-03-20	Substituted quinolinonyl and dihydroquinolinonyl tetrazolinone herbicides
CN116457340A (zh)	2023-07-18	杀真菌芳基脒
DE19909541A1 (de)	1999-10-14	Herbizide 2-Aryloxy- bzw. 2-Arylthio-6-arylpyrimidine
JPH0356447A (ja)	1991-03-12	新規除草剤組成物
KR850000209B1 (ko)	1985-03-06	3-이속사졸리디논의 제조방법