IL124022A - -5 amino acids that have undergone acylation, a process for their preparation and their use in insect control - Google Patents

-5 amino acids that have undergone acylation, a process for their preparation and their use in insect control

Info

Publication number: IL124022A
Authority: IL; Israel
Prior art keywords: halogen atoms; alkyl; optionally substituted; chlorine; fluorine
Prior art date: 1995-11-14

Application number

IL12402296A

Other languages

English (en)

Hebrew (he)

Original Assignee

Bayer Ag

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.)

1995-11-14

Filing date

1996-11-04

Publication date

2001-05-20

1996-11-04 Application filed by Bayer Ag filed Critical Bayer Ag

2001-05-20 Publication of IL124022A publication Critical patent/IL124022A/en

Links

238000002360 preparation method Methods 0.000 title claims description 55
238000000034 method Methods 0.000 title claims description 42
230000008569 process Effects 0.000 title claims description 40
GKZNVLJEHYUFIC-UHFFFAOYSA-N 1,2-thiazol-5-amine Chemical class NC1=CC=NS1 GKZNVLJEHYUFIC-UHFFFAOYSA-N 0.000 title claims description 18
241000238631 Hexapoda Species 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 132
-1 halogenoalkylthio Chemical group 0.000 claims abstract description 96
229910052736 halogen Inorganic materials 0.000 claims abstract description 25
150000002367 halogens Chemical group 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 9
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
125000004450 alkenylene group Chemical group 0.000 claims abstract description 4
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims abstract description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000005529 alkyleneoxy group Chemical group 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 4
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims description 81
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 60
229910052731 fluorine Inorganic materials 0.000 claims description 60
239000011737 fluorine Substances 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 43
239000000460 chlorine Substances 0.000 claims description 38
229910052801 chlorine Inorganic materials 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
239000003085 diluting agent Substances 0.000 claims description 25
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
241000607479 Yersinia pestis Species 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 7
230000002140 halogenating effect Effects 0.000 claims description 7
230000000802 nitrating effect Effects 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 6
239000007800 oxidant agent Substances 0.000 claims description 6
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 5
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
IJUDUPSHUGIGMT-IHWYPQMZSA-N (z)-3-aminobut-2-enethioamide Chemical class C\C(N)=C\C(N)=S IJUDUPSHUGIGMT-IHWYPQMZSA-N 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
239000004606 Fillers/Extenders Substances 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
BAPZCSMFCUVUHW-UHFFFAOYSA-N dichloro(fluoro)methane Chemical compound F[C](Cl)Cl BAPZCSMFCUVUHW-UHFFFAOYSA-N 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 abstract description 10
239000002904 solvent Substances 0.000 description 43
125000001309 chloro group Chemical group Cl* 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000012360 testing method Methods 0.000 description 33
239000000126 substance Substances 0.000 description 29
239000003995 emulsifying agent Substances 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000009472 formulation Methods 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000012141 concentrate Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical class CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
230000006378 damage Effects 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000011161 development Methods 0.000 description 12
230000018109 developmental process Effects 0.000 description 12
229920000151 polyglycol Polymers 0.000 description 12
239000010695 polyglycol Substances 0.000 description 12
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 11
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 11
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 10
239000011230 binding agent Substances 0.000 description 10
239000000839 emulsion Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002023 wood Substances 0.000 description 10
241000255925 Diptera Species 0.000 description 9
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
240000007124 Brassica oleracea Species 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
239000011877 solvent mixture Substances 0.000 description 8
241000238876 Acari Species 0.000 description 7
125000002877 alkyl aryl group Chemical group 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000008187 granular material Substances 0.000 description 7
239000002917 insecticide Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
238000001035 drying Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000417 fungicide Substances 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
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239000000843 powder Substances 0.000 description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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238000002955 isolation Methods 0.000 description 5
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
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WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
235000015112 vegetable and seed oil Nutrition 0.000 description 4
239000008158 vegetable oil Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
230000019617 pupation Effects 0.000 description 1
QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
229940015367 pyrethrum Drugs 0.000 description 1
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
229960003811 pyrithione disulfide Drugs 0.000 description 1
XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
235000010296 thiabendazole Nutrition 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
229960004546 thiabendazole Drugs 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229940074152 thuringiensin Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
- C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

IL12402296A 1995-11-14 1996-11-04 -5 amino acids that have undergone acylation, a process for their preparation and their use in insect control IL124022A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19542372A DE19542372A1 (de)	1995-11-14	1995-11-14	Acylierte 5-Aminoisothiazole
PCT/EP1996/004796 WO1997018198A1 (de)	1995-11-14	1996-11-04	Acylierte 5-aminoisothiazole mit insektizider wirkung, zwischenprodukte und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
IL124022A true IL124022A (en)	2001-05-20

Family

ID=7777402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12402296A IL124022A (en)	1995-11-14	1996-11-04	-5 amino acids that have undergone acylation, a process for their preparation and their use in insect control

Country Status (14)

Country	Link
US (2)	US5972843A (2)
EP (1)	EP0861241B1 (2)
JP (1)	JP2000502046A (2)
KR (1)	KR19990064325A (2)
CN (1)	CN1071749C (2)
AU (1)	AU7563396A (2)
BR (1)	BR9611475A (2)
DE (2)	DE19542372A1 (2)
ES (1)	ES2215199T3 (2)
ID (1)	ID17719A (2)
IL (1)	IL124022A (2)
MX (1)	MX9803629A (2)
TW (1)	TW343130B (2)
WO (1)	WO1997018198A1 (2)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19628569A1 (de) *	1996-07-16	1998-01-22	Bayer Ag	Substituierte N-(5-Isothiazolyl)-thioamide
DE19727162A1 (de) *	1997-06-26	1999-01-07	Bayer Ag	Substituierte Aminoheterocyclylamide
DE19736545A1 (de) *	1997-08-22	1999-02-25	Bayer Ag	Acylierte 5-Aminoisothiazole
GB9816654D0 (en)	1998-07-30	1998-09-30	Zeneca Ltd	Chemical compounds
DE19846008A1 (de)	1998-10-06	2000-04-13	Bayer Ag	Phenylessigsäure-heterocyclylamide
US6320050B1 (en) *	1999-03-29	2001-11-20	Hoffmann-La Roche Inc.	Heteroaromatic glucokinase activators
US6610846B1 (en)	1999-03-29	2003-08-26	Hoffman-La Roche Inc.	Heteroaromatic glucokinase activators
CN1384832A (zh) *	1999-11-18	2002-12-11	诺瓦提斯公司	作为农药的氨基杂环基酰胺化合物
BR0015909A (pt) *	1999-11-29	2002-08-06	Novartis Ag	N-heteroaril alfa-alcoximino-carboxamidas pesticidas
AU2010601A (en) *	1999-12-16	2001-07-03	Novartis Ag	Organic compounds
GB0002034D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002029D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002036D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002040D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002031D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002032D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
PE20010830A1 (es)	2000-01-28	2001-09-06	Syngenta Ltd	Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
DE10015015A1 (de) *	2000-03-27	2001-10-04	Bayer Ag	Oxim-Derivate
US6667326B1 (en)	2000-11-16	2003-12-23	Novartis Animal Health Us, Inc.	Pesticidal aminoheterocyclamide compounds
JP2006514039A (ja) *	2002-12-20	2006-04-27	ビーエーエスエフ　アクチェンゲゼルシャフト	トリアゾロピリミジン、その調製、および有害な菌類の防除のための使用、ならびにこれらの化合物を含む組成物
US20060135455A1 (en)	2004-06-01	2006-06-22	Reza Sheikhnejad	Methods and compositions for the inhibition of gene expression
EP3000480A1 (en)	2005-12-01	2016-03-30	ProNAi Therapeutics, Inc.	Cancer therapies and pharmaceutical compositions used therein
EP2076502B1 (en) *	2006-06-08	2011-05-18	Eli Lilly And Company	Substituted carboxamides as group i metabotropic receptor antagonists
CN104884637A (zh)	2012-11-05	2015-09-02	普隆奈治疗公司	利用生物标志物通过bcl2表达的调节治疗癌症的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1924830A1 (de) *	1968-07-06	1970-11-19	Merck Patent Gmbh	Neues Verfahren zur Herstellung von 5-Acylamino-isothiazolderivaten
ES2055808T3 (es) *	1988-03-21	1994-09-01	Ciba Geigy Ag	Agente para la proteccion de plantas contra enfermedades.
JPH072604A (ja) *	1993-05-05	1995-01-06	Shell Internatl Res Maatschappij Bv	殺虫方法および農薬化合物
DE4328425A1 (de) *	1993-08-24	1995-03-02	Basf Ag	Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung
CA2189573A1 (en) *	1994-05-17	1995-11-23	Ronald E. Hackler	N-(5-isothiazolyl)amide pesticides

1995
- 1995-11-14 DE DE19542372A patent/DE19542372A1/de not_active Withdrawn
1996
- 1996-11-04 IL IL12402296A patent/IL124022A/en not_active IP Right Cessation
- 1996-11-04 US US09/068,598 patent/US5972843A/en not_active Expired - Fee Related
- 1996-11-04 ES ES96938067T patent/ES2215199T3/es not_active Expired - Lifetime
- 1996-11-04 DE DE59610983T patent/DE59610983D1/de not_active Expired - Fee Related
- 1996-11-04 WO PCT/EP1996/004796 patent/WO1997018198A1/de not_active Ceased
- 1996-11-04 KR KR1019980702824A patent/KR19990064325A/ko not_active Abandoned
- 1996-11-04 JP JP9518545A patent/JP2000502046A/ja not_active Ceased
- 1996-11-04 CN CN96198283A patent/CN1071749C/zh not_active Expired - Fee Related
- 1996-11-04 EP EP96938067A patent/EP0861241B1/de not_active Expired - Lifetime
- 1996-11-04 AU AU75633/96A patent/AU7563396A/en not_active Abandoned
- 1996-11-04 BR BR9611475A patent/BR9611475A/pt not_active IP Right Cessation
- 1996-11-11 TW TW085113741A patent/TW343130B/zh active
- 1996-11-13 ID IDP963306A patent/ID17719A/id unknown
1998
- 1998-05-07 MX MX9803629A patent/MX9803629A/es unknown
1999
- 1999-06-22 US US09/338,484 patent/US6008366A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HK1017675A1 (en)	1999-11-26
US5972843A (en)	1999-10-26
DE19542372A1 (de)	1997-05-15
ES2215199T3 (es)	2004-10-01
WO1997018198A1 (de)	1997-05-22
CN1202162A (zh)	1998-12-16
CN1071749C (zh)	2001-09-26
AU7563396A (en)	1997-06-05
KR19990064325A (ko)	1999-07-26
MX9803629A (es)	1998-09-30
DE59610983D1 (de)	2004-05-19
BR9611475A (pt)	1999-07-13
US6008366A (en)	1999-12-28
EP0861241A1 (de)	1998-09-02
ID17719A (id)	1998-01-22
TW343130B (en)	1998-10-21
JP2000502046A (ja)	2000-02-22
EP0861241B1 (de)	2004-04-14

Legal Events

Date	Code	Title	Description
2003-01-12	KB	Patent renewed
2007-07-24	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AU726611B2 (en)	2000-11-16	3-thiocarbamoylpyrazole derivatives as pesticides
US6008366A (en)	1999-12-28	Acylated 5-aminoisothiazoles with insecticidal properties, intermediate products and process for producing them
US5942528A (en)	1999-08-24	Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides
US5973162A (en)	1999-10-26	Substituted thiazolines and their use for controlling animal pests
DE19628569A1 (de)	1998-01-22	Substituierte N-(5-Isothiazolyl)-thioamide
KR20000029574A (ko)	2000-05-25	치환ｎ-이소티아졸일-(티오)아미드
EP0970059B1 (de)	2003-08-20	Disubstituierte biphenyloxazoline
US5994551A (en)	1999-11-30	1-heterocyclyl methyl-2-nitro-or-cyanoiminidazoline salts, process for their preparation, pesticidal composition containing them, and pesticidal method of using them
US6414000B1 (en)	2002-07-02	Substituted diphenyl oxazolin derivatives with insecticidal effect
EP0993451A1 (de)	2000-04-19	2-(2-methylphenyl)-oxazoline
US6335325B1 (en)	2002-01-01	Acylated 4-aminopyridine derivatives as pesticides and fungicides
US6015823A (en)	2000-01-18	4-Cyclohexylphenyl-oxazolines and their use for controlling animal pests
AU8111198A (en)	1999-01-19	Substituted aminoheterocyclylamides
CA2248018A1 (en)	1997-09-12	Tetrahydropyrimidine derivatives
KR20000075506A (ko)	2000-12-15	이치환 비페닐옥사졸린
CA2245875A1 (en)	1997-08-21	Salts from imidazoline derivatives and their use as a parasite control agent
MXPA99000423A (en)	1999-09-20	N- (5-isotiazolyl) -tioamides substitui
DE19718522A1 (de)	1998-09-10	Disubstituierte Biphenyloxazoline
MXPA99001056A (en)	2000-01-01	Substituted n-isothiazolyl-(thio)amides
MXPA97003193A (en)	1998-07-03	Esters of fluorbutenilo, its employment for the luchacontra the pimes anima
DE19757223A1 (de)	1999-06-24	Disubstituierte Biphenyloxazoline