SK69293A3

SK69293A3 - Safening pesticidal interactions in crops

Safening pesticidal interactions in crops Download PDF

Info

Publication number: SK69293A3
Authority: SK; Slovakia
Prior art keywords: methyl; chloro; alkyl; sulfonamide; dimethyl
Prior art date: 1990-12-31

Application number

SK69293A

Other languages

English (en)

Slovak (sk)

Inventor

Brett H Bussler

Harrison R Hakes

David J Mayonado

Original Assignee

Monsanto Co

Priority date

1990-12-31

Filing date

1991-12-30

Publication date

1993-10-06

1991-12-20 Priority claimed from US07/808,590 external-priority patent/US5484760A/en

1991-12-30 Application filed by Monsanto Co filed Critical Monsanto Co

1993-10-06 Publication of SK69293A3 publication Critical patent/SK69293A3/sk

Links

230000003993 interaction Effects 0.000 title claims abstract description 82
230000000361 pesticidal effect Effects 0.000 title description 2
230000002363 herbicidal effect Effects 0.000 claims abstract description 459
150000001875 compounds Chemical class 0.000 claims abstract description 199
230000003115 biocidal effect Effects 0.000 claims abstract description 160
230000000749 insecticidal effect Effects 0.000 claims abstract description 13
230000000855 fungicidal effect Effects 0.000 claims abstract description 6
239000004009 herbicide Substances 0.000 claims description 445
239000000729 antidote Substances 0.000 claims description 383
-1 1,3-dioxolan-2-ylmethyl Chemical group 0.000 claims description 367
239000002917 insecticide Substances 0.000 claims description 164
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 157
239000003139 biocide Substances 0.000 claims description 150
240000008042 Zea mays Species 0.000 claims description 128
238000000034 method Methods 0.000 claims description 128
239000000203 mixture Substances 0.000 claims description 120
125000000217 alkyl group Chemical group 0.000 claims description 104
229940075522 antidotes Drugs 0.000 claims description 88
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 76
235000005822 corn Nutrition 0.000 claims description 76
125000003545 alkoxy group Chemical group 0.000 claims description 68
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
229910052736 halogen Inorganic materials 0.000 claims description 63
230000005764 inhibitory process Effects 0.000 claims description 55
229940124530 sulfonamide Drugs 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 51
XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 46
125000001188 haloalkyl group Chemical group 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 40
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 33
RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 32
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 31
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 24
229940100389 Sulfonylurea Drugs 0.000 claims description 22
FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical compound ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims description 21
229910004013 NO 2 Inorganic materials 0.000 claims description 21
SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 claims description 19
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000002252 acyl group Chemical group 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 15
235000021307 Triticum Nutrition 0.000 claims description 15
125000003282 alkyl amino group Chemical group 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
239000005645 nematicide Substances 0.000 claims description 13
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 12
239000005586 Nicosulfuron Substances 0.000 claims description 12
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical group COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 12
150000003456 sulfonamides Chemical class 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
239000005944 Chlorpyrifos Substances 0.000 claims description 11
229920000742 Cotton Polymers 0.000 claims description 11
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 10
VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
240000007594 Oryza sativa Species 0.000 claims description 9
235000007164 Oryza sativa Nutrition 0.000 claims description 9
235000011684 Sorghum saccharatum Nutrition 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000000417 fungicide Substances 0.000 claims description 9
235000009566 rice Nutrition 0.000 claims description 9
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 8
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 claims description 8
QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 claims description 8
125000003302 alkenyloxy group Chemical group 0.000 claims description 8
125000005133 alkynyloxy group Chemical group 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
230000001603 reducing effect Effects 0.000 claims description 8
MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 8
WFVUIONFJOAYPK-SDNWHVSQSA-N (z)-n-(1,3-dioxolan-2-ylmethoxy)benzenecarboximidoyl cyanide Chemical compound C=1C=CC=CC=1C(/C#N)=N/OCC1OCCO1 WFVUIONFJOAYPK-SDNWHVSQSA-N 0.000 claims description 7
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims description 7
235000010469 Glycine max Nutrition 0.000 claims description 7
YZAJGNMSFKRIGI-UHFFFAOYSA-N N1C(S(=O)(=O)N)=NC=C2N=CC=C21 Chemical compound N1C(S(=O)(=O)N)=NC=C2N=CC=C21 YZAJGNMSFKRIGI-UHFFFAOYSA-N 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 6
CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 6
244000068988 Glycine max Species 0.000 claims description 6
GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 6
YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 6
OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 5
AIELWRZUDWJQFM-UHFFFAOYSA-N 3-ethylpyridine-4-carboxylic acid Chemical compound CCC1=CN=CC=C1C(O)=O AIELWRZUDWJQFM-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
241000607479 Yersinia pestis Species 0.000 claims description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims description 5
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
LQPRNRFJJUSONA-UHFFFAOYSA-N methyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OC)C1=CC=CC=C1 LQPRNRFJJUSONA-UHFFFAOYSA-N 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
GVNKDIIUOKNRIO-UHFFFAOYSA-N 2-(5-chloroquinolin-8-yl)oxyacetonitrile Chemical compound C1=CC=C2C(Cl)=CC=C(OCC#N)C2=N1 GVNKDIIUOKNRIO-UHFFFAOYSA-N 0.000 claims description 4
GZEVGNINWVUGFO-UHFFFAOYSA-N 2-chloro-n-[1-(2,4,6-trimethylphenyl)ethenyl]acetamide Chemical compound CC1=CC(C)=C(C(=C)NC(=O)CCl)C(C)=C1 GZEVGNINWVUGFO-UHFFFAOYSA-N 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
239000005947 Dimethoate Substances 0.000 claims description 4
239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 claims description 4
239000005580 Metazachlor Substances 0.000 claims description 4
239000005950 Oxamyl Substances 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical group NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 claims description 4
125000005159 cyanoalkoxy group Chemical group 0.000 claims description 4
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
125000004494 ethyl ester group Chemical group 0.000 claims description 4
ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
229960003512 nicotinic acid Drugs 0.000 claims description 4
239000011664 nicotinic acid Substances 0.000 claims description 4
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 4
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
ZOICEMKCAHAKTR-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazol-3-yl)ethanone Chemical compound CC1(C)OC=CN1C(=O)C(Cl)Cl ZOICEMKCAHAKTR-UHFFFAOYSA-N 0.000 claims description 3
SXSNYZPSATVORJ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CC=C1 SXSNYZPSATVORJ-UHFFFAOYSA-N 0.000 claims description 3
BIXDGFXKRPNCKF-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-5-thiophen-2-yl-1,3-oxazolidin-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CS1 BIXDGFXKRPNCKF-UHFFFAOYSA-N 0.000 claims description 3
LFILUHIBZWXBQH-UHFFFAOYSA-N 2,2-dichloro-1-(3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)CCCC2=C1 LFILUHIBZWXBQH-UHFFFAOYSA-N 0.000 claims description 3
XQFKDWFJAFIUJY-UHFFFAOYSA-N 2,2-dichloro-1-(5-methoxy-2,2-dimethyl-1,3-oxazol-3-yl)ethanone Chemical compound COC1=CN(C(=O)C(Cl)Cl)C(C)(C)O1 XQFKDWFJAFIUJY-UHFFFAOYSA-N 0.000 claims description 3
SFOUCQQYDOZWQR-UHFFFAOYSA-N 2-chloro-n-(1,2-diethylcyclohexa-2,4-dien-1-yl)-n-(methoxymethyl)acetamide Chemical compound CCC1=CC=CCC1(CC)N(COC)C(=O)CCl SFOUCQQYDOZWQR-UHFFFAOYSA-N 0.000 claims description 3
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical group ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 3
JEDZOXJDXQBZIA-UHFFFAOYSA-N 2-methyl-2-(4-methylphenyl)sulfanylpent-4-enenitrile Chemical compound CC1=CC=C(SC(C)(CC=C)C#N)C=C1 JEDZOXJDXQBZIA-UHFFFAOYSA-N 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 3
239000005745 Captan Substances 0.000 claims description 3
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