AP506A - Insecticidal substituted-2,4-diaminoquinazolines. - Google Patents

Insecticidal substituted-2,4-diaminoquinazolines. Download PDF

Info

Publication number: AP506A
Authority: AP; ARIPO
Prior art keywords: hydrogen; substituted; phenyl; grams; alkyl
Prior art date: 1993-02-18

Application number

APAP/P/1994/000620A

Other languages

English (en)

Other versions

AP9400620A0 (en

Inventor

11 Robert Neil HENRIE

Clinton Joseph Peake

Thomas Gerard Cullen

Albert C Lew

Munirathnam Krishnappa Chaguturu

Partha Sarathi Ray

Original Assignee

Fmc Corp

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.)

1993-02-18

Filing date

1994-02-16

Publication date

1996-07-18

1994-02-16 Application filed by Fmc Corp filed Critical Fmc Corp

1994-04-30 Publication of AP9400620A0 publication Critical patent/AP9400620A0/xx

1996-07-18 Application granted granted Critical

1996-07-18 Publication of AP506A publication Critical patent/AP506A/en

Links

230000000749 insecticidal effect Effects 0.000 title claims abstract description 28
-1 substituted-2,4-diaminoquinazolines Chemical class 0.000 title claims description 102
239000000203 mixture Substances 0.000 claims abstract description 85
150000001875 compounds Chemical class 0.000 claims description 130
229910052739 hydrogen Inorganic materials 0.000 claims description 108
239000001257 hydrogen Substances 0.000 claims description 108
125000000217 alkyl group Chemical group 0.000 claims description 91
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
125000001188 haloalkyl group Chemical group 0.000 claims description 48
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
125000003118 aryl group Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical group 0.000 claims description 42
238000000034 method Methods 0.000 claims description 40
241000238631 Hexapoda Species 0.000 claims description 36
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
125000005843 halogen group Chemical group 0.000 claims description 26
125000003435 aroyl group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical compound C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 claims description 17
125000001544 thienyl group Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000004438 haloalkoxy group Chemical group 0.000 claims description 13
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000004103 aminoalkyl group Chemical group 0.000 claims description 10
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
125000003107 substituted aryl group Chemical group 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000005128 aryl amino alkyl group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
MHOGSCSQSBBPMN-UHFFFAOYSA-N 5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline-2,4-diamine Chemical group COC1=CC=C(Cl)C=C1C1=CC=C(N=C(N)N=C2N)C2=C1Cl MHOGSCSQSBBPMN-UHFFFAOYSA-N 0.000 claims description 6
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
125000005110 aryl thio group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
UROLJHNFAMBGBG-UHFFFAOYSA-N 6-(5-chlorothiophen-2-yl)-5-methylquinazoline-2,4-diamine Chemical group C1=CC2=NC(N)=NC(N)=C2C(C)=C1C1=CC=C(Cl)S1 UROLJHNFAMBGBG-UHFFFAOYSA-N 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000005015 aryl alkynyl group Chemical group 0.000 claims description 5
125000005353 silylalkyl group Chemical group 0.000 claims description 5
229910052720 vanadium Inorganic materials 0.000 claims description 5
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
229910052721 tungsten Inorganic materials 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
NRTSBIXZLAAFOY-UHFFFAOYSA-N 5-chloro-6-[5-chloro-2-(pyridin-2-ylmethoxy)phenyl]quinazoline-2,4-diamine Chemical group C1=CC2=NC(N)=NC(N)=C2C(Cl)=C1C1=CC(Cl)=CC=C1OCC1=CC=CC=N1 NRTSBIXZLAAFOY-UHFFFAOYSA-N 0.000 claims description 3
OCBGWBGACJFTCD-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-5-methylquinazoline-2,4-diamine Chemical group C1=CC2=NC(N)=NC(N)=C2C(C)=C1C1=CC(Cl)=CC(Cl)=C1 OCBGWBGACJFTCD-UHFFFAOYSA-N 0.000 claims description 3
229910014033 C-OH Inorganic materials 0.000 claims description 3
229910014570 C—OH Inorganic materials 0.000 claims description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
ROVBCNXBXPJQKK-UHFFFAOYSA-N (2,4-diamino-5-methylquinazolin-6-yl)-[4-(trifluoromethyl)phenyl]methanone Chemical group C1=CC2=NC(N)=NC(N)=C2C(C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1 ROVBCNXBXPJQKK-UHFFFAOYSA-N 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
HLHBMQSAXBFTOZ-UHFFFAOYSA-N 6-[3,5-bis(trifluoromethyl)phenyl]-5-methylquinazoline-2,4-diamine Chemical group C1=CC2=NC(N)=NC(N)=C2C(C)=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HLHBMQSAXBFTOZ-UHFFFAOYSA-N 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 119
238000003786 synthesis reaction Methods 0.000 description 118
239000011541 reaction mixture Substances 0.000 description 98
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 86
239000000543 intermediate Substances 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
239000000460 chlorine Substances 0.000 description 67
239000000243 solution Substances 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
239000007787 solid Substances 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
238000007792 addition Methods 0.000 description 35
239000000047 product Substances 0.000 description 35
239000000706 filtrate Substances 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 33
238000012360 testing method Methods 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000003054 catalyst Substances 0.000 description 28
238000001914 filtration Methods 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 23
230000009036 growth inhibition Effects 0.000 description 22
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
150000003246 quinazolines Chemical class 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
238000010828 elution Methods 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
238000004440 column chromatography Methods 0.000 description 19
BUTTVUBNXIIXRH-UHFFFAOYSA-N 1-(cyclopropylmethyl)pyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CC1CC1 BUTTVUBNXIIXRH-UHFFFAOYSA-N 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 17
239000000126 substance Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
229910052801 chlorine Inorganic materials 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 13
241000256244 Heliothis virescens Species 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
235000005911 diet Nutrition 0.000 description 11
230000037213 diet Effects 0.000 description 11
239000000284 extract Substances 0.000 description 11
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
229910052731 fluorine Inorganic materials 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
229910000029 sodium carbonate Inorganic materials 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
229960000443 hydrochloric acid Drugs 0.000 description 9
235000011167 hydrochloric acid Nutrition 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 8
NFJSIWUQYGVKTE-UHFFFAOYSA-N 6-amino-3-bromo-2-methylbenzonitrile Chemical compound CC1=C(Br)C=CC(N)=C1C#N NFJSIWUQYGVKTE-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
239000002917 insecticide Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
230000012010 growth Effects 0.000 description 7
PKOMYWHVCYHAHW-UHFFFAOYSA-N 2-amino-6-methylbenzonitrile Chemical compound CC1=CC=CC(N)=C1C#N PKOMYWHVCYHAHW-UHFFFAOYSA-N 0.000 description 6
VCQUJWHUIPJFDH-UHFFFAOYSA-N 6-amino-3-bromo-2-chlorobenzonitrile Chemical compound NC1=CC=C(Br)C(Cl)=C1C#N VCQUJWHUIPJFDH-UHFFFAOYSA-N 0.000 description 6
AMDSTKMVXKCMGU-UHFFFAOYSA-N 6-amino-3-iodo-2-methylbenzonitrile Chemical compound CC1=C(I)C=CC(N)=C1C#N AMDSTKMVXKCMGU-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
229910000564 Raney nickel Inorganic materials 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000010410 layer Substances 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000007921 spray Substances 0.000 description 6
239000012258 stirred mixture Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 6
JZWXVYNQIJJTKF-UHFFFAOYSA-N 5-chloroquinazoline-2,4,6-triamine Chemical compound N1=C(N)N=C(N)C2=C(Cl)C(N)=CC=C21 JZWXVYNQIJJTKF-UHFFFAOYSA-N 0.000 description 5
JDGJWDGCZGJUJJ-UHFFFAOYSA-N 6-(2-phenylethyl)quinazoline-2,4-diamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=CC=C1 JDGJWDGCZGJUJJ-UHFFFAOYSA-N 0.000 description 5
QNNPAYVFMMNZIX-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)sulfanylquinazoline-2,4-diamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1SC1=CC=C(Cl)C(Cl)=C1 QNNPAYVFMMNZIX-UHFFFAOYSA-N 0.000 description 5
UVBLYZRPSXSSQT-UHFFFAOYSA-N 6-chloro-2-methyl-3-nitrobenzonitrile Chemical compound CC1=C([N+]([O-])=O)C=CC(Cl)=C1C#N UVBLYZRPSXSSQT-UHFFFAOYSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
241000256247 Spodoptera exigua Species 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000969 carrier Substances 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
FMBVAOHFMSQDGT-UHFFFAOYSA-N (5-chloro-2-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(Cl)C=C1B(O)O FMBVAOHFMSQDGT-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
LJBWEZVYRBKOCI-UHFFFAOYSA-N 2,4,6-triaminoquinazoline Chemical compound N1=C(N)N=C(N)C2=CC(N)=CC=C21 LJBWEZVYRBKOCI-UHFFFAOYSA-N 0.000 description 4
MNPVYSUCMALGIH-UHFFFAOYSA-N 2-amino-5-(2-phenylethyl)benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1CCC1=CC=CC=C1 MNPVYSUCMALGIH-UHFFFAOYSA-N 0.000 description 4
VUEJEHJVMVAHBF-UHFFFAOYSA-N 2-amino-5-(2-phenylethynyl)benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C#CC1=CC=CC=C1 VUEJEHJVMVAHBF-UHFFFAOYSA-N 0.000 description 4
OATYCBHROMXWJO-UHFFFAOYSA-N 2-amino-5-bromobenzonitrile Chemical compound NC1=CC=C(Br)C=C1C#N OATYCBHROMXWJO-UHFFFAOYSA-N 0.000 description 4
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
229940093475 2-ethoxyethanol Drugs 0.000 description 4
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 4
URWKLBQFDCAUCU-UHFFFAOYSA-N 4-chloro-2-(2,4-diamino-5-chloroquinazolin-6-yl)phenol Chemical compound C1=CC2=NC(N)=NC(N)=C2C(Cl)=C1C1=CC(Cl)=CC=C1O URWKLBQFDCAUCU-UHFFFAOYSA-N 0.000 description 4
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CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
235000010523 Cicer arietinum Nutrition 0.000 description 1
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
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PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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239000005645 nematicide Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
WRFWTEUKNIYWHE-UHFFFAOYSA-N quinazoline-2-diazonium Chemical class C1=CC=CC2=NC([N+]#N)=NC=C21 WRFWTEUKNIYWHE-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
AJSNKAWQAAHVQV-UHFFFAOYSA-N tert-butyl n-[6-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]quinazolin-4-yl]carbamate Chemical compound C1=CC2=NC(NC(=O)OC(C)(C)C)=NC(NC(=O)OC(C)(C)C)=C2C(C)=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AJSNKAWQAAHVQV-UHFFFAOYSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
229960001099 trimetrexate Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

APAP/P/1994/000620A 1993-02-18 1994-02-16 Insecticidal substituted-2,4-diaminoquinazolines. AP506A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1938993A	1993-02-18	1993-02-18
US14949193A	1993-11-09	1993-11-09

Publications (2)

Publication Number	Publication Date
AP9400620A0 AP9400620A0 (en)	1994-04-30
AP506A true AP506A (en)	1996-07-18

Family

ID=26692173

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
APAP/P/1994/000620A AP506A (en)	1993-02-18	1994-02-16	Insecticidal substituted-2,4-diaminoquinazolines.
APAP/P/1996/000796A AP507A (en)	1993-02-18	1996-02-16	Novel insecticidal 2,4-diaminoquinazolines.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1996/000796A AP507A (en)	1993-02-18	1996-02-16	Novel insecticidal 2,4-diaminoquinazolines.

Country Status (10)

Country	Link
US (3)	US5534518A (fr)
EP (1)	EP0684824A4 (fr)
AP (2)	AP506A (fr)
AU (1)	AU6298694A (fr)
IL (1)	IL108630A0 (fr)
MA (1)	MA23116A1 (fr)
MX (1)	MX9401249A (fr)
TN (1)	TNSN94014A1 (fr)
TW (1)	TW315298B (fr)
WO (1)	WO1994018980A1 (fr)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR012634A1 (es) *	1997-05-02	2000-11-08	Sugen Inc	Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion
JP4370002B2 (ja) *	1997-08-08	2009-11-25	富山化学工業株式会社	キノロンカルボン酸誘導体またはその塩
MY122278A (en)	1999-07-19	2006-04-29	Upjohn Co	1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
US7030109B2 (en)	1999-07-19	2006-04-18	Pharmacia & Upjohn Company	1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
CA2413723C (fr) *	2000-06-30	2010-01-12	Basf Aktiengesellschaft	Procede de fabrication de derives de la 4-bromo-aniline
PE20020506A1 (es) *	2000-08-22	2002-07-09	Glaxo Group Ltd	Derivados de pirazol fusionados como inhibidores de la proteina cinasa
WO2002068397A1 (fr) *	2001-02-28	2002-09-06	Melacure Therapeutics Ab	Esters de diaminoquinazoline esters destines a etre utilises avec des inhibiteurs de la dihydrofolate reductase
GB0124931D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124936D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124933D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124939D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
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Also Published As

Publication number	Publication date
US5874579A (en)	1999-02-23
AP507A (en)	1996-07-18
EP0684824A4 (fr)	1996-02-14
TNSN94014A1 (fr)	1995-04-25
US5616718A (en)	1997-04-01
TW315298B (fr)	1997-09-11
AU6298694A (en)	1994-09-14
US5534518A (en)	1996-07-09
AP9400620A0 (en)	1994-04-30
IL108630A0 (en)	1994-05-30
WO1994018980A1 (fr)	1994-09-01
AP9600796A0 (en)	1996-04-30
MA23116A1 (fr)	1994-10-01
EP0684824A1 (fr)	1995-12-06
MX9401249A (es)	1994-08-31

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JP3353895B2 (ja)	2002-12-03	有害生物防除性ピリミジン化合物類
EP0438209B1 (fr)	1994-09-21	Dérivés de l'uracil et pesticides contenant ces dérivés comme agent actif
KR920006738B1 (ko)	1992-08-17	2-아닐리노 피리미딘 유도체
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JPH10182614A (ja)	1998-07-07	殺寄生生物性化合物
JPH07165730A (ja)	1995-06-27	新規の農薬
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AU673222B2 (en)	1996-10-31	Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives
WO1994027439A1 (fr)	1994-12-08	Pteridines et 8-desazapteridines inscticides
JPH0699407B2 (ja)	1994-12-07	農薬ピリミジニル安息香酸及びエステル
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JPH06192252A (ja)	1994-07-12	ピラジン誘導体および除草剤
KR0149513B1 (ko)	1998-10-15	우라실 유도체 및 활성성분으로서 이를 함유하는 농약
JPH09176170A (ja)	1997-07-08	殺微生物剤
JPH0725857A (ja)	1995-01-27	縮合ヘテロ環誘導体及び除草剤
RU2060250C1 (ru)	1996-05-20	Производные гидантоина, способ их получения, промежуточные соединения, гербицидная композиция на основе производных гидантоина и способ борьбы с сорняками
JP2530155B2 (ja)	1996-09-04	２−フエノキシピリミジン誘導体および除草剤
JPH07502756A (ja)	1995-03-23	新規の除草剤
JPS62207262A (ja)	1987-09-11	ピリダジノン誘導体、その製法および殺虫、殺ダニ、殺線虫、殺菌剤
JPH02131480A (ja)	1990-05-21	ピリジルピリミジン誘導体およびそれを有効成分とする農園芸用殺菌剤