AR059885A1 - SELECTIVE INSECTICIDES BASED ON PHTALIC ACID DIAMIDS AND DETOXIFYING AGENTS - Google Patents
SELECTIVE INSECTICIDES BASED ON PHTALIC ACID DIAMIDS AND DETOXIFYING AGENTSInfo
- Publication number
- AR059885A1 AR059885A1 ARP070100919A ARP070100919A AR059885A1 AR 059885 A1 AR059885 A1 AR 059885A1 AR P070100919 A ARP070100919 A AR P070100919A AR P070100919 A ARP070100919 A AR P070100919A AR 059885 A1 AR059885 A1 AR 059885A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- acid
- cyano
- halogen
- ester
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 13
- 239000003795 chemical substances by application Substances 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 title 1
- -1 1-methyl-hexyl Chemical group 0.000 abstract 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 19
- 229910052736 halogen Inorganic materials 0.000 abstract 17
- 150000002367 halogens Chemical class 0.000 abstract 17
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 8
- 229910052794 bromium Inorganic materials 0.000 abstract 8
- 229910052801 chlorine Inorganic materials 0.000 abstract 8
- 239000000460 chlorine Substances 0.000 abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052731 fluorine Inorganic materials 0.000 abstract 7
- 239000011737 fluorine Substances 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 abstract 4
- 125000002541 furyl group Chemical group 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 3
- 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 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 abstract 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 abstract 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 abstract 2
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 abstract 2
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 abstract 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 abstract 2
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 125000000335 thiazolyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- VXJKYWLPNZBSMY-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(naphthalen-1-ylsulfamoyl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC=C12 VXJKYWLPNZBSMY-UHFFFAOYSA-N 0.000 abstract 1
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 abstract 1
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 abstract 1
- AJFKCJRMHHBFNS-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1N=C(C(=O)O)C=C1C1=CC=CC=C1 AJFKCJRMHHBFNS-UHFFFAOYSA-N 0.000 abstract 1
- MQPLQJSDTDAHBC-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-propan-2-ylpyrazole-3-carboxylic acid Chemical compound CC(C)C1=CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl MQPLQJSDTDAHBC-UHFFFAOYSA-N 0.000 abstract 1
- AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 abstract 1
- OISQRMLHYOLTJL-UHFFFAOYSA-N 2,2-dichloro-n-(1,3-dioxolan-2-ylmethyl)-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC1OCCO1 OISQRMLHYOLTJL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002794 2,4-DB Substances 0.000 abstract 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract 1
- AXHCGXRBOHBEQA-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C=C1OCC(O)=O AXHCGXRBOHBEQA-UHFFFAOYSA-N 0.000 abstract 1
- IQDCEFNXFAZHCY-SECPXAEJSA-N 2-amino-9-[(1R,6R,8R,10S,15R,17R,18R)-3,12,18-trihydroxy-3,12-dioxo-8-pyrimidin-4-yloxy-2,4,11,13,16-pentaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound N1=C(O[C@@H]2C[C@@H]3COP(=O)(O[C@@H]4[C@@H]([C@@H](COP(=O)(O[C@H]3C2)O)O[C@H]4N2C3=C(N=C2)C(=O)NC(=N3)N)O)O)C=CN=C1 IQDCEFNXFAZHCY-SECPXAEJSA-N 0.000 abstract 1
- KWGQOJWITMQEOT-UHFFFAOYSA-N 2-benzhydryloxyacetic acid Chemical compound C=1C=CC=CC=1C(OCC(=O)O)C1=CC=CC=C1 KWGQOJWITMQEOT-UHFFFAOYSA-N 0.000 abstract 1
- OGZUWSFEZCBGPH-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(Cl)=NC=1C(F)(F)F OGZUWSFEZCBGPH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 abstract 1
- ULKOQNVFHBGETA-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-phenyl-4h-1,2-oxazole Chemical compound C1=CC(F)=CC=C1C1(C=2C=CC=CC=2)ON=CC1 ULKOQNVFHBGETA-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 abstract 1
- 239000005504 Dicamba Substances 0.000 abstract 1
- 102220467487 Drebrin_R10G_mutation Human genes 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- 239000005574 MCPA Substances 0.000 abstract 1
- 102220578763 Mapk-regulated corepressor-interacting protein 1_R20D_mutation Human genes 0.000 abstract 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 abstract 1
- 102220471536 Replication factor C subunit 4_R17D_mutation Human genes 0.000 abstract 1
- 102220510525 Retinoic acid receptor alpha_R14D_mutation Human genes 0.000 abstract 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 244000038559 crop plants Species 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 abstract 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 abstract 1
- IVEMKPKJNOWXSK-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C)N1C1=CC=C(Cl)C=C1Cl IVEMKPKJNOWXSK-UHFFFAOYSA-N 0.000 abstract 1
- JEMXUSHXYOXNFL-UHFFFAOYSA-N ethyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC)=CC=C(Cl)C2=C1 JEMXUSHXYOXNFL-UHFFFAOYSA-N 0.000 abstract 1
- VZZVOKHLRXJIEP-UHFFFAOYSA-N ethyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OCC)C1=CC=CC=C1 VZZVOKHLRXJIEP-UHFFFAOYSA-N 0.000 abstract 1
- YNZGZAJXHXGDBF-UHFFFAOYSA-N ethyl 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1C1=CC=CC=C1 YNZGZAJXHXGDBF-UHFFFAOYSA-N 0.000 abstract 1
- WWHBBYNEFXJGME-UHFFFAOYSA-N ethyl 5-tert-butyl-1-(2,4-dichlorophenyl)pyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C(C)(C)C)N1C1=CC=C(Cl)C=C1Cl WWHBBYNEFXJGME-UHFFFAOYSA-N 0.000 abstract 1
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- NDQZMBNEHYSVPL-UHFFFAOYSA-N methyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC)=CC=C(Cl)C2=C1 NDQZMBNEHYSVPL-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- CMCJQHLLWDPWPK-UHFFFAOYSA-N n-[4-(cyclopropylcarbamoyl)phenyl]sulfonyl-2-methoxy-5-methylbenzamide Chemical compound COC1=CC=C(C)C=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 CMCJQHLLWDPWPK-UHFFFAOYSA-N 0.000 abstract 1
- NYDKNJDNBUFWRJ-UHFFFAOYSA-N n-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)N(C)C)C=C1 NYDKNJDNBUFWRJ-UHFFFAOYSA-N 0.000 abstract 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 abstract 1
- HFGGXBQZQRVOKM-UHFFFAOYSA-N piperidine-1-carbothioic s-acid Chemical compound SC(=O)N1CCCCC1 HFGGXBQZQRVOKM-UHFFFAOYSA-N 0.000 abstract 1
- BQTKTWVNANAGJC-UHFFFAOYSA-N prop-2-enyl 2-propyloctanedithioate Chemical compound CCCC(CCCCCC)C(=S)SCC=C BQTKTWVNANAGJC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Reivindicacion 1: Agente que contiene (a) al menos una diamida del ácido ftálico de formula (1) en la que Hal representa cloro, bromo o yodo, * designa un átomo de carbono en la configuracion R o S, preferentemente en la configuracion S, y (b) al menos un compuesto que mejora la fitotolerancia en plantas de cultivo del siguiente grupo de compuestos: 4-Dicloroacetil-1-oxa-4-aza-espiro[4.5]-decano (AD-67, MON-4660), 1-dicloroacetil-hexahidro-3,3,8S-trimetilpirrolo[1,2-a]-pirimidin-6(2H)-ona (diciclonona, BAS-145138), 4-dicloroacetil-3,4-dihidro-3-metil-2H-1,4-benzoxazina (benoxacor), éster, 1-metil-hexílico del ácido 5-cloro-quinolin-8-oxi-acético (cloquintocet mexilo; véanse también los compuestos relacionados en los documentos EP-A- 0086750, EP-A-0094349, EP-A-0191736, EP-A-0492366), 3-(2-clorobencil)-1-(1-metil-1-feniletil)-urea (cumiluron), alfa-(cianometoximino)-fenilacetonitrilo (ciometrinilo), ácido 2,4-dicloro-fenoxiacético (2,4-D), ácido 4-(2,4-diclorofenoxi)-butírico (2,4-DB), 1-(1-metil-1-feniletil)-3-(4-metilfenil)-urea (daimuron, dieron), ácido 3,6-dicloro-2-metoxibenzoico (dicamba), éster S-1-metil-1-feniletílico del ácido piperidin-1-tiocarboxílico (dimepiperato), 2,2-dicloro-N-(2-oxo-2-(2-propenilamino)- etil)-N-(2-propenil)-acetamida (DKA-24), 2,2-dicloro-N,N-di-2-propenilacetamida (diclormid), 4,6-dicloro-2-fenil-pirimidina (fenclorim), éter etílico del ácido 1-(2,4-dicloro-fenil)-5-triclorometil-1H-1,2,4-triazol-3-carboxílico (fenclorazol etilo; véanse también los compuestos relacionados en los documentos EP-A-0174562 y EP-A-0346620), éster fenilmetílico del ácido 2-cloro-4-trifluorometil-tiazol-5-carboxílico (flurazol), 4-cloro-N-(1,3-dioxolan-2-il-metoxi)-alfa-trifluoro-acetofenonoxima (fluxofenim), 3-dicloroacetil-5-(2-furanil)-2,2-dimetil-oxazolidina (furilazol, MON-13900), 4,5-dihidro-5,5-difenil-3-isoxazolcarboxilato de etilo (isoxadifen etilo; véanse también los compuestos relacionados en el documento WO 95/07897), 3,6- dicloro-2-metoxibenzoato de 1-(etoxicarbonil)-etilo(lactidicloro), ácido (4-cloro-o-toliloxi)-acético (MCPA), ácido 2-(4-cloro-o-toliloxi)-propionico (mecoprop), 1-(2,4-diclorofenil)-4,5-dihidro-5-metil-1H-pirazol-3,5-dicarboxilato de dietilo (mefenpir dietilo; véanse también los compuestos relacionados en el documento WO 91/07874), 2-diclorometil-2-metil-1,3-dioxolano (MG-191), 1-oxa-4-azaespiro[4.5]decano-4-carboditioato de 2-propenilo (MG-838), anhídrido de ácido 1,8-naftálico, alfa- (1,3-dioxilan-2-il-metoximino)-fenilacetonitrilo (oxabentrinilo), 2,2-dicloro-N-(1,3-dioxolan-2-il-metil)-N-(2-propenil)-acetamida(PPG-1292), 3-dicloroacetil-2,2-dimetiloxazolidina (R-28725), 3-dicloroacetil-2,2,5-trimetiloxalidina (R-29148), ácido 4-(4-cloro-o-tolil)-butírico, ácido 4-(4-clorofenoxi)-butírico, ácido difenilmetoxiacético, éster metílico del ácido difenilmetoxiacético, éster etílico del ácido difenilmetoxiacético, éster metílico del ácido 1-(2-clorofenil)-5-fenil-1H-pirazol-3- carboxílico, éster etílico del ácido 1-(2,4-diclorofenil)-5-metil-1H-pirazol-3-carboxílico, éster etílico del ácido 1-(2,4-diclorofenil)-5-isopropil-1H-pirazol-3-carboxílico, éster etílico del ácido 1-(2,4-diclorofenil)-5-(1,1-dimetiletil)-1H- pirazol-3-carboxílico, éster etílico del ácido 1-(2,4-diclorofenil)-5-fenil-1H-pirazol-3-carboxílico (véase también los compuestos relacionados en los documentos EP-A-0269806 y EP-A-0333131), éster etílico del ácido 5-(2,4-diclorobencil)-2- isoxazolin-3-carboxílico, éster etílico del ácido 5-fenil-2-isoxazolin-3-carboxílico, éster etílico del ácido 5-(4-fluorofenil)-5-fenil-2-isoxazolin-3-carboxílico (veánse los compuestos relacionados en el documento WO 91/08202), éster 1,3-dimetil- but-1-ílico del ácido 5-cloroquinolin-8-oxiacético, éster 4-aliloxibutílico del ácido 5-cloroquinolin-8-oxiacético, éster 1-aliloxiprop-2-ílico del ácido 5-cloroquinolin-8-oxiacético, éster metílico del ácido 5-cloroquinolin-8-oxiacético, éster etílico del ácido 5-cloroquinolin-8-oxiacético, éster alílico del ácido 5-cloroquinolin-8-oxiacético, éster 2-oxoprop-1-ílico del ácido 5-cloroquinolin-8-oxiacético, éster dietílico del ácido 5-cloroquinolin-8-oximalonico, éster dialílico del ácido 5-cloroquinolin-8-oximalonico, éster dietílico del ácido 5-cloroquinolin-8-oximalonico (véanse también los compuestos relacionados en el documento EP-A-0582198), ácido 4-carboxi-croman-4-ilacético (AC-304415, véase el documento EP-A-0613618), ácido 4-clorofenoxiacético, 3,3'-dimetil-4-metoxi-benzofenona, 1-bromo-4-clorometilsulfonilbenceno, 1-[4-(N-2-metoxibenzoilsulfamoil)-fenil]-3-metilurea (alias N-(2-metoxibenzoil)-4-[(metilaminocarbonil)-amino]-bencenosulfonamida), 1-[4-(N-2- metoxibenzoilsulfamoil)-fenil]-3,3-dimetilurea, 1-[4-(N-4,5-dimetil-benzoilsulfamoil)-fenil]-3-metilurea, 1-[4-(N-naftilsulfamoil)-fenil]-3,3-dimetilurea, N-(2-metoxi-5-metilbenzoil)-4-(ciclopropilaminocarbonil)-bencenosulfonamida, o un resto del grupo de formulas (2) en las que r representa 0, 1, 2, 3, 4 o 5, A1D representa una de las agrupaciones heterocíclicas divalentes del grupo de formulas (3); s representa 0, 1, 2, 3, 4 o 5, A2D representa alcanodiilo C1-2 dado el caso sustituido con alquilo C1-4, alcoxicarbonilo C1-4 y/o alqueniloxicarbonilo C1-4, R8D representa hidroxi, mercapto, amino, alcoxi C1-6, alquiltio C1-6, alquilamino C1-6 o di-(alquil-C1-4)-amino, R9D representa hidroxi, mercapto, amino, alcoxi C1-7, alqueniloxi C1-6- , alqueniloxi-C1-6-alcoxi-C1-6, alquiltio C1-6, alquilamino C1-6 o di-(alquil-C1-4)-amino, R10D representa alquilo C1-4 dado el caso sustituido respectivamente con fluor, cloro y/o bromo, R11D representa hidrogeno, alquilo C1-6, alquenilo C2-6 o alquinilo C2-6, alcoxi-C1-4-alquilo-C1-4, dioxolanilalquilo C1-4, furilo, furilalquilo C1-4, tienilo, tiazolilo, piperidinilo dado el caso sustituidos respectivamente con fluor, cloro y/o bromo, o fenilo dado el caso sustituido con fluor, cloro y/o bromo o alquilo C1-4, R12D representa hidrogeno o alquilo C1-6, alquenilo C2-6 o alquinilo C2-6, alcoxi-C1-4-alquilo C1-4, dioxolanilalquilo C1-4, furilo, furilalquilo C1-4, tienilo, tiazolilo, piperidinilo dado el caso sustituidos respectivamente con fluor, cloro y/o bromo, o fenilo dado el caso sustituido con fluor, cloro y/o bromo o alquilo C1-4, R11d y R12D también representan juntos alcanodiilo C3-6 u oxaalcanodiilo C2-5 dado el caso sustituidos respectivamente con alquilo C1-4, fenilo, furilo, un anillo de benceno condensado o con dos sustituyentes que, junto con el átomo de C al que están unidos, forman un carbociclo de 5 o 6 miembros, R13D representa hidrogeno, ciano, halogeno, o alquilo C1-4, cicloalquilo C3-6 o fenilo dado el caso sustituidos respectivamente con fluor, cloro y/o bromo, R14D representa hidrogeno o alquilo C1-6, cicloalquilo C3-6 o tri-(alquil C1-4)-sililo sustituido dado el caso con hidroxi, ciano, halogeno o alcoxi C1-4, R15D representa hidrogeno, ciano, halogeno o alquilo C1-4, cicloalquilo C3-6 o fenilo dado el caso sustituidos respectivamente con fluor, cloro y/o bromo, X1D representa nitro, ciano, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxiC1-4 o haloalcoxi C1-4, X2D representa hidrogeno, ciano, nitro, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4, X3D representa hidrogeno, ciano, nitro, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4, y/o uno de los siguientes compuestos de las formulas generales (4), (5) en las que t representa 0, 1, 2, 3, 4 o 5, v representa 0, 1, 2, 3 o 4, R16D representa hidrogeno o alquilo C1-4, R17D representa hidrogeno o alquilo C1-4, R18D representa hidrogeno o alquilo C1-6, alcoxi C1-6, alquiltio C1-6, alquil-C1-6-amino o di-(alquil-C1-4)-amino dado el caso sustituidos respectivamente con ciano, halogeno o alcoxi C1-4, o cicloalquilo C3-6, cicloalquiloxi C3-6, cicloalquiltio C3-6 o cicloalquil-C3-6-amino dado el caso sustituidos respectivamente con ciano, halogeno o alquilo C1-4, R19D representa hidrogeno o alquilo C1-6 dado el caso sustituido con ciano, hidroxi, halogeno o alcoxi c1-4, o alquenilo c3-6 o alquinilo C3-6 dado el caso sustituidos respectivamente con ciano o halogeno, o cicloalquilo C3-6 dado el caso sustituido con ciano, halogeno o alquilo C1-4, R20D representa hidrogeno o alquilo C1-6 dado el caso sustituido con ciano, hidroxi, halogeno o alcoxi C1-4, o alquenilo C3-6 o alquinilo C3-6 dado el caso sustituidos respectivamente con ciano o halogeno, o cicloalquilo C3-6 dado el caso sustituido con ciano, halogeno o alquilo C1-4, o fenilo dado el caso sustituido con nitro, ciano, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4, o representa junto con R10D alcanodiilo C2-6 u oxaalcanodiilo C2-5 dado el caso sustituidos respectivamente con alquilo C1-4, X4D representa nitro, ciano, carboxi, carbamoílo, formilo, sulfamoílo, hidroxi, amino, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxi c1-4 o haloalcoxi C1-4, y X5D representa nitro, ciano, carboxi, carbamoílo, formilo, sulfamoílo, hidroxi, amino, halogeno, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4 o haloalcoxi C1-4.Claim 1: Agent containing (a) at least one diamide of the phthalic acid of formula (1) in which Hal represents chlorine, bromine or iodine, * designates a carbon atom in the R or S configuration, preferably in the S configuration , and (b) at least one compound that improves phytotolerance in crop plants of the following group of compounds: 4-Dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67, MON-4660) , 1-dichloroacetyl-hexahydro-3,3,8S-trimethylpyrrolo [1,2-a] -pyrimidin-6 (2H) -one (dicylonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3- methyl-2H-1,4-benzoxazine (benoxacor), ester, 1-methyl-hexyl of 5-chloro-quinolin-8-oxy-acetic acid (cloquintocet mexyl; see also the related compounds in EP-A-0086750 , EP-A-0094349, EP-A-0191736, EP-A-0492366), 3- (2-Chlorobenzyl) -1- (1-methyl-1-phenylethyl) -urea (cumiluron), alpha- (cyanomethoximine) -phenylacetonitrile (cyometrinyl), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4- (2,4-dichlorophenoxy) -butyri acid co (2,4-DB), 1- (1-methyl-1-phenylethyl) -3- (4-methylphenyl) -urea (daimuron, gave), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethyl ester of piperidin-1-thiocarboxylic acid (dimepiperate), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2- propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenylacetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 1- ethyl acid ether (2,4-Dichloro-phenyl) -5-trichloromethyl-1H-1,2,4-triazol-3-carboxylic acid (pheclorazol ethyl; see also the related compounds in EP-A-0174562 and EP-A-0346620), phenylmethyl ester of 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid (flurazole), 4-chloro-N- (1 , 3-dioxolan-2-yl-methoxy) -alpha-trifluoro-acetophenonoxime (fluxophenim), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furylazole, MON-13900), 4, Ethyl 5-dihydro-5,5-diphenyl-3-isoxazolcarboxylate (ethyl isoxadifen; see also related compounds in WO 95/07897), 3- (ethoxycarbonyl) -3,6-dichloro-2-methoxybenzoate (lactidichloro), (4-chloro-o-tolyloxy) -acetic acid (MCPA), 2- (4-chloro-o-tolyloxy) -propionic acid (mecoprop), 1- (2,4-dichlorophenyl) -4, Diethyl 5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylate (mefenpyr diethyl; see also related compounds in WO 91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1-oxa-4-azaspiro [4.5] 2-propenyl decane-4-carbodithioate (MG-838), 1,8-naphthalic acid anhydride, alpha- ( 1,3-dioxylan-2-yl-methoximino) -phenylacetonitrile (oxabentrinyl), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide ( PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxalidine (R-29148), 4- (4-chloro-o-tolyl) acid - butyric acid, 4- (4-chlorophenoxy) -butyric acid, diphenylmethoxyacetic acid, diphenylmethoxyacetic acid methyl ester, diphenylmethoxyacetic acid ethyl ester, 1- (2-chlorophenyl) -5-phenyl-1H-pyrazole-3- methyl ester carboxylic acid, 1- (2,4-dichlorophenyl) -5-methyl-1 H -pyrazol-3-carboxylic acid ethyl ester, 1- (2,4-dichlorophenyl) -5-isopropyl-1 H -pyrazol- 3-carboxylic acid, 1- (2,4-dichlorophenyl) -5- (1,1-dimethylethyl) -1 H- pyrazol-3-carboxylic acid ethyl ester, 1- (2,4-dichlorophenyl) - 5-phenyl-1H-pyrazol-3-carboxylic acid (see also the related compounds in EP-A-0269806 and EP-A-0333131), 5- (2-acid ethyl ester) , 4-dichlorobenzyl) -2-isoxazolin-3-carboxylic acid, 5-phenyl-2-isoxazolin-3-carboxylic acid ethyl ester, 5- (4-fluorophenyl) -5-phenyl-2-isoxazolin- acid ethyl ester 3-carboxylic acid (see related compounds in WO 91/08202), 1,3-dimethyl-but-1-yl ester of 5-chloroquinolin-8-oxyacetic acid, 4-allyloxybutyl ester of 5-chloroquinolin-8 acid -oxyacetic, 5-chloroquinolin-8-oxyacetic acid 1-allyloxypropyl-2-yl acid ester, 5-chloroquinoline-8-oxyacetic acid methyl ester, 5-chloroquinoline-8-oxyacetic acid ethyl ester, 5-allyl acidic ester -chloroquinolin-8-oxyacetic acid, 2-oxoprop-1-yl ester of 5-chloroquinolin-8-oxyacetic acid, diethyl ester of 5-chloroquinolin-8-oxyalonic acid, diallyl ester of 5-chloroquinolin-8-oximalonic acid, ester 5-chloroquinolin-8-oxyalonic acid diethyl (see also related compounds in EP-A-0582198), 4-carboxy-chroman-4- acid ilacetic (AC-304415, see EP-A-0613618), 4-chlorophenoxyacetic acid, 3,3'-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulfonylbenzene, 1- [4- (N- 2-Methoxybenzoylsulfamoyl) -phenyl] -3-methylurea (aka N- (2-methoxybenzoyl) -4 - [(methylaminocarbonyl) -amino] -benzenesulfonamide), 1- [4- (N-2- methoxybenzoylsulfamoyl) -phenyl] - 3,3-dimethylurea, 1- [4- (N-4,5-dimethyl-benzoylsulfamoyl) -phenyl] -3-methylurea, 1- [4- (N-naphthylsulfamoyl) -phenyl] -3,3-dimethylurea, N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, or a remainder of the group of formulas (2) in which r represents 0, 1, 2, 3, 4 or 5, A1D represents a of the divalent heterocyclic groupings of the group of formulas (3); s represents 0, 1, 2, 3, 4 or 5, A2D represents C1-2 alkanediyl, where appropriate substituted with C1-4 alkyl, C1-4 alkoxycarbonyl and / or C1-4 alkenyloxycarbonyl, R8D represents hydroxy, mercapto, amino, C1-6 alkoxy, C1-6 alkylthio, C1-6 alkylamino or di- (C1-4 alkyl) -amino, R9D represents hydroxy, mercapto, amino, C1-7 alkoxy, C1-6 alkenyloxy, C1- alkenyloxy 6-C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylamino or di- (C 1-4 alkyl) -amino, R 10 D represents C 1-4 alkyl, where appropriate substituted respectively with fluorine, chlorine and / or bromine, R11D represents hydrogen, C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, C 1-4 alkoxy, C 1-4 dioxolanylalkyl, furyl, C 1-4 furyl alkyl, thienyl, thiazolyl, piperidinyl given the case respectively substituted with fluorine, chlorine and / or bromine, or phenyl, if necessary substituted with fluorine, chlorine and / or bromine or C1-4 alkyl, R12D represents hydrogen or C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl , C1-4 alkoxy-C1-4 alkyl, dioxyl alkylalkyl C1-4, furyl, furyl C1-4 chyl, thienyl, thiazolyl, piperidinyl if substituted respectively with fluorine, chlorine and / or bromine, or phenyl if necessary substituted with fluorine, chlorine and / or bromine or C1-4 alkyl, R11d and R12D also together represent C3-6 alkanediyl or C2-5 oxaalkanediyl optionally substituted with C1-4 alkyl, phenyl, furyl, a condensed benzene ring or with two substituents which, together with the C atom to which they are attached, form a carbocycle of 5 or 6 members, R13D represents hydrogen, cyano, halogen, or C1-4 alkyl, C3-6 cycloalkyl or phenyl, respectively substituted with fluorine, chlorine and / or bromine, R14D represents hydrogen or C1-6 alkyl, C3 cycloalkyl -6 or tri- (C1-4 alkyl) -silyl substituted as appropriate with hydroxy, cyano, halogen or C1-4 alkoxy, R15D represents hydrogen, cyano, halogen or C1-4 alkyl, C3-6 cycloalkyl or phenyl given the case respectively substituted with fluorine, chlorine and / or bromine, X1D represents nitro, cyano, halogen, alq C1-4 uyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy, X2D represents hydrogen, cyano, nitro, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy, X3D represents hydrogen, cyano, nitro, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy, and / or one of the following compounds of the general formulas (4), (5) in the that t represents 0, 1, 2, 3, 4 or 5, v represents 0, 1, 2, 3 or 4, R16D represents hydrogen or C1-4 alkyl, R17D represents hydrogen or C1-4 alkyl, R18D represents hydrogen or alkyl C 1-6, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkyl-amino or di- (C 1-4 alkyl) -amino, respectively substituted with cyano, halogen or C 1-4 alkoxy, or cycloalkyl C3-6, C3-6 cycloalkyloxy, C3-6 cycloalkylthio or C3-6-cycloalkyl, if substituted respectively with cyano, halogen or C1-4 alkyl, R19D represents hydrogen or C1-6 alkyl if necessary substituted with cyano , hydroxy, halogen or C1-4 alkoxy, or C3-6 alkenyl or alkyl C3-6 nyl, if necessary substituted respectively with cyano or halogen, or C3-6 cycloalkyl, if necessary substituted with cyano, halogen or C1-4alkyl, R20D represents hydrogen or C1-6alkyl, if necessary substituted with cyano, hydroxy, halogen or C1-4 alkoxy, or C3-6 alkenyl or C3-6 alkynyl if necessary respectively substituted with cyano or halogen, or C3-6 cycloalkyl, if necessary substituted with cyano, halogen or C1-4 alkyl, or phenyl if case substituted with nitro, cyano, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy, or represents together with R10D C2-6 alkanediyl or C2-5 oxaalkanediyl, respectively substituted respectively with alkyl C1-4, X4D represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy, and X5D represents nitro, cyano , carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or ha C1-4 loalkoxy.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200610010203 DE102006010203A1 (en) | 2006-03-06 | 2006-03-06 | Selective insecticides based on phthalic diamides and safeners |
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| AR059885A1 true AR059885A1 (en) | 2008-05-07 |
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| ARP070100919A AR059885A1 (en) | 2006-03-06 | 2007-03-06 | SELECTIVE INSECTICIDES BASED ON PHTALIC ACID DIAMIDS AND DETOXIFYING AGENTS |
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| AR (1) | AR059885A1 (en) |
| DE (1) | DE102006010203A1 (en) |
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| WO (1) | WO2007101543A2 (en) |
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| EP2964027B1 (en) | 2013-03-05 | 2019-04-24 | Bayer CropScience AG | Use of combinations comprising cloquintocet-mexyl for improving plant yield |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
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| DE102004035134A1 (en) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selective insecticides based on Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden or phthalic diamides and safeners |
| ZA200701486B (en) * | 2004-08-23 | 2008-07-30 | Nihon Nohyaku Co Ltd | Optically active phthalamide derivative, agricultural or horticultural insecticide, and method of using the same |
| JP2006089469A (en) * | 2004-08-23 | 2006-04-06 | Nippon Nohyaku Co Ltd | Optically active phthalamide derivatives, agricultural and horticultural insecticides and methods of use thereof |
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2006
- 2006-03-06 DE DE200610010203 patent/DE102006010203A1/en not_active Withdrawn
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2007
- 2007-02-21 WO PCT/EP2007/001462 patent/WO2007101543A2/en not_active Ceased
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| DE102006010203A1 (en) | 2007-09-13 |
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