JP2012512211A - 除草および殺虫効果のある4−フェニル置換ピリダジノン類 - Google Patents
除草および殺虫効果のある4−フェニル置換ピリダジノン類 Download PDFInfo
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- JP2012512211A JP2012512211A JP2011541180A JP2011541180A JP2012512211A JP 2012512211 A JP2012512211 A JP 2012512211A JP 2011541180 A JP2011541180 A JP 2011541180A JP 2011541180 A JP2011541180 A JP 2011541180A JP 2012512211 A JP2012512211 A JP 2012512211A
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- Prior art keywords
- alkyl
- hydrogen
- substituted
- alkoxy
- halogen
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- Granted
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- 230000002363 herbicidal effect Effects 0.000 title claims description 24
- 230000000749 insecticidal effect Effects 0.000 title description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 2
- -1 phenyl-substituted pyridazinones Chemical class 0.000 claims abstract description 182
- 239000001257 hydrogen Substances 0.000 claims abstract description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 137
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 119
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 44
- 150000002367 halogens Chemical group 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 239000002917 insecticide Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 212
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- 239000000203 mixture Substances 0.000 claims description 51
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 230000009261 transgenic effect Effects 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
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- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical compound O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
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- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002829 nitrogen Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 18
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- 239000002253 acid Substances 0.000 description 15
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- 230000000694 effects Effects 0.000 description 14
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical group CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Aは、それぞれの場合において互いに独立して、水素、(C3−C6)シクロアルキルまたは(C1−C6)アルキル(ハロゲン、(C3−C6)シクロアルキル、フェニルおよびハロフェニルからなる群からのn個の基で置換されている。)であり;
Bは、互いに独立して、(C3−C6)シクロアルキルまたは(C1−C6)アルキル(ハロゲン、(C3−C6)シクロアルキル、フェニルおよびハロフェニルからなる群からのn個の基で置換されている。)であり;
mは、0、1、2または3であり;
nは、0、1、2または3であるが、但し、mおよびnは、両方とも0であることはなく;
Gは、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7、EまたはR8であり;
Eは、金属イオン等価物またはアンモニウムイオンであり;
Lは、酸素または硫黄であり;
Mは、酸素または硫黄であり;
R1は、それぞれn個のハロゲン原子で置換されている、(C1−C6)アルキル、(C2−C6)アルケニル、(C1−C4)アルコキシ−(C1−C6)アルキル、ジ−(C1−C4)アルコキシ−(C1−C6)アルキルまたは(C1−C4)アルキルチオ−(C1−C6)アルキル;
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、3から5個の炭素原子ならびに酸素、硫黄および窒素からなる群からの1から3個のヘテロ原子からなる完全飽和の3員から6員の環;
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、(C3−C6)シクロアルキル、フェニル、フェニル−(C1−C4)アルキル、ヘテロアリール、フェノキシ−(C1−C4)アルキルまたはヘテロアリールオキシ−(C1−C4)アルキルであり;
R2は、(C1−C6)アルキル、(C2−C6)アルケニル、(C1−C4)アルコキシ−(C1−C6)アルキルもしくはジ−(C1−C4)アルコキシ−(C1−C6)アルキルであり、それぞれn個のハロゲン原子で置換されている、または
(C3−C6)シクロアルキル、フェニルもしくはベンジルであり、それぞれ、ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R3、R4およびR5は、それぞれ互いに独立して、(C1−C6)アルキル(n個のハロゲン原子で置換されている)、(C1−C4)アルコキシ、N−(C1−C6)アルキルアミノ、N,N−ジ−(C1−C6)アルキルアミノ、(C1−C4)アルキルチオ、(C2−C4)アルケニルもしくは(C3−C6)シクロアルキルチオである、または
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、フェニル、ベンジル、フェノキシもしくはフェニルチオであり;
R6およびR7は、それぞれ互いに独立して、水素である、
(C1−C6)アルキル(n個のハロゲン原子で置換されている)、(C3−C6)シクロアルキル、(C2−C6)アルケニル、(C1−C6)アルコキシもしくは(C1−C4)アルコキシ−(C1−C6)アルキルである、
フェニルもしくはベンジルであり、それぞれ、ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている;または
R6およびR7は、それらが結合している窒素原子と一緒になって、2から5個の炭素原子および0もしくは1個の酸素もしくは硫黄原子を含有する、3員から6員の環を形成し;
a)Xは、水素、(C1−C6)アルキルもしくは(C3−C6)シクロアルキルであり;
Yは、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、(C1−C6)アルコキシである、もしくはn個のハロゲン原子で置換されているフェニルであり;
Zは、水素、ハロゲン、シアノ、ニトロ、(C1−C6)アルキル、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキルである、もしくはn個のハロゲン原子で置換されているフェニルである;または
b)Xは、ハロゲン、シアノ、ニトロである、もしくは(C1−C6)アルキル、(C3−C6)シクロアルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれ、n個のハロゲン原子で置換されており;
YおよびZは、それぞれ互いに独立して、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、もしくは(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されている。]。
Aが、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C6)アルキル、ベンジル、ハロフェニル−(C1−C6)アルキルである、またはn個のハロゲン原子で置換されている(C1−C6)アルキルであり;
Bが、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C6)アルキル、ベンジル、ハロフェニル−(C1−C6)アルキルである、またはn個のハロゲン原子で置換されている(C1−C6)アルキルであり;
mが、0、1、2または3であり:
nが、0、1、2または3であるが、但し、mおよびnが、両方とも0であることはなく;
Gが、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7またはEであり;
Eが、Na+、K+、(Mg2+)1/2、(Ca2+)1/2、R13R14R15R16N+またはNH4 +であり;
R13、R14、R15およびR16が、互いに独立して、(C1−C6)アルキルまたはベンジルであり;
Lが、酸素であり;
Mが、酸素であり;
R1が、n個のハロゲン原子で置換されている(C1−C6)アルキルである、または(C3−C6)シクロアルキル、フェニルもしくはフェニル−(C1−C4)アルキルであり、それぞれハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R2が、n個のハロゲン原子で置換されている(C1−C6)アルキルである、または(C3−C6)シクロアルキル、フェニルもしくはベンジルであり、それぞれハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R3、R4およびR5が、それぞれ互いに独立して、n個のハロゲン原子で置換されている(C1−C6)アルキルである、またはハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されているフェニルもしくはベンジルであり;
R6およびR7が、それぞれ互いに独立して、水素、n個のハロゲン原子で置換されている(C1−C6)アルキルである、またはハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、フェニルもしくはベンジルであり;
a)Xが、水素、メチル、エチルまたはシクロプロピルであり;
Yが、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、(C1−C6)アルコキシ、もしくはn個のハロゲン原子で置換されているフェニルであり;
Zが、水素、ハロゲン、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、もしくはn個のハロゲン原子で置換されているフェニルである;または
b)Xが、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C1−C6)アルコキシもしくは(C3−C6)シクロアルキルであり;
Yが、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されており;
Zが、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、もしくは(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されている
の一般式(I)の化合物である。
Aが、シクロプロピル、シクロプロピルメチル、ベンジル、2−クロロフェニルメチル、3−クロロフェニルメチルまたは4−クロロフェニルメチルであり;
Bが、水素、2,2−ジフルオロエチル、2,2,2−トリフルオロエチル、シクロプロピル、シクロプロピルメチル、ベンジル、2−クロロフェニルメチル、3−クロロフェニルメチルまたは4−クロロフェニルメチルであり;
Gが、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7、EまたはR8であり;
Eが、Na+、K+、(Mg2+)1/2、(Ca2+)1/2、(CH3)4N+またはNH4 +であり;
Lが、酸素であり;
Mが、酸素であり;
R1が、(C1−C6)アルキルまたは(C3−C6)シクロアルキルであり;
R2が、(C1−C6)アルキル、(C3−C6)シクロアルキルまたはベンジルであり;
R3、R4およびR5が、それぞれ互いに独立して、(C1−C6)アルキル、フェニルまたはベンジルであり;
R6およびR7が、それぞれ互いに独立して、水素、(C1−C6)アルキル、フェニルまたはベンジルであり;
a)Xが、水素、メチルもしくはエチルであり;
Yが、フッ素、臭素、塩素、ヨウ素、シアノ、ニトロ、シクロプロピル、メトキシ、エトキシ、トリフルオロメチルもしくはトリフルオロメトキシ、フェニルもしくはハロフェニルであり;
Zが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチルもしくはシクロプロピルである;または
b)Xが、フッ素、臭素、塩素、ヨウ素、シアノ、ニトロ、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシもしくはシクロプロピルであり;
Yが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシもしくはシクロプロピルであり;
Zが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシ、シクロプロピル、クロロフェニルもしくはフルオロフェニルである
の一般式(I)の化合物である。
Bz=ベンジル c−Pr=シクロプロピル Et=エチル
i−Bu=イソブチル t−Bu=第三級ブチル i−Pr=イソプロピル
Me=メチル Ph=フェニル c=シクロ
−植物内に合成されるデンプンを改変する目的の作物植物の組み換え改変(例えば、WO92/11376、WO92/14827、WO91/19806)、
−グルホシネート型(例えば、EP−A−0242236、EP−A−242246を参照すること)またはグリフォセート型(WO92/00377)またはスルホニル尿素型(EP−A−0257993、US−A−5013659)の特定の除草剤に対して耐性であるトランスジェニック作物植物、
−特定の病害虫に対して植物を耐性にする、バキルルス・トゥリンギエンシス(Bacillus thuringiensis)毒素(Bt毒素)を生成することができるトランスジェニック作物植物、例えば綿(EP−A−0142924、EP−A−0193259)、
−改変された脂肪酸組成を有するトランスジェニック作物植物(WO91/13972)、
−新規構成成分または二次代謝産物、例えば、病害耐性の増加をもたらす新規フィトアレキシンを有する遺伝子改変作物植物(EPA309862、EPA0464461)、
−より高い収量およびより高いストレス耐性が特徴である、光呼吸の低減を有する遺伝子改変植物(EPA0305398)、
−薬学的または診断的に重要なタンパク質を生成するトランスジェニック作物植物(「分子ファーミング」)、
−より高い収量またはより良好な品質によって際立っているトランスジェニック作物植物、
−例えば上記記述の新規特性の組み合わせ(「遺伝子スタッキング」)によって際立っているトランスジェニック作物植物。
<0°で、10mlのDMFおよび0.53g(2.0mmol)のエチル2−シクロブチル−{[2−(2,4−ジクロロフェニル)アセチル]ヒドラゾノ}プロピオネートの溶液を、10mlのDMF中の0.331g(2当量)のカリウムt−ブトキシドに2時間かけて滴下添加した。混合物を0°で90分間撹拌し、次に反応溶液を100mlの冷却0.5N塩酸に注いだ。溶液を減圧下で濃縮し、水に取り、もう一度濃縮し、50mlの水に取った。混合物を、それぞれの場合に50mlの酢酸エチルで2回抽出し、合わせた有機相を硫酸ナトリウムで脱水し、減圧下で濃縮し、カラムクロマトグラフィー(シリカゲル、n−ヘプタン/EtOAcの勾配)により精製した。このことによって、0.1gの純粋な生成物を得た。
0.25g(0.74mmol)の、表91の本発明の化合物I−1−a−5、0.12gのジイソプロピルエチルアミン(1.3当量)およびへら先のDMAPを、15mlの酢酸エチルに最初に投入し、環流下で沸騰するまで加熱した。次に0.058g(1.0当量)の塩化アセチルを2mlの酢酸エチルに溶解し、10分間かけて滴下添加した。混合物を5時間撹拌し、別の0.04gのジイソプロピルアミンおよび0.02gの塩化アセチルを加え、さらに2時間の反応時間の後、混合物を冷却し、20mlの水および50mlの酢酸エチルを加えた。有機相を分離し、乾燥し、クロマトグラフ精製(シリカゲル、酢酸エチル/n−ヘプタンの勾配)の後、0.04gの純粋な生成物を得た。
1.25g(0.61mmol)の、表91の本発明の化合物番号I−1−a−7を、30mlのジクロロメタンに最初に投入し、0.438gのトリエチルアミンおよび0.36gのクロロギ酸エチルを加えた。混合物を室温で一晩撹拌し、次に30mlの5%濃度の重炭酸ナトリウム溶液を加えた。有機相を分離し、次に乾燥し、濃縮し、カラムクロマトグラフィー(シリカゲル、酢酸エチル/n−ヘプタンの勾配)により精製した。酢酸エチル/n−ヘプタンからの結晶化により、0.28gの純粋な生成物を得た。
0.14g(0.3mmol)の、表91の本発明の化合物番号I−1−a−10を、10mlのジクロロメタンに最初に投入し、0.039gのトリエチルアミンおよび0.034gの塩化メタンスルホニルを加えた。混合物を室温で一晩撹拌し、次に5mlの水を加えた。有機相を分離し、次に乾燥し、濃縮し、カラムクロマトグラフィー(シリカゲル、酢酸エチル/n−ヘプタンの勾配)により精製した。酢酸エチル/n−ヘプタンからの結晶化により、0.15gの純粋な生成物を得た。
3.22g(26.4mmol)のベンジルヒドラジンを4.4ml(1.2当量)のトリエチルアミンおよび0.16g(0.05当量)のDMAPと一緒に、50mlのジクロロメタンに最初に投入し、次に50mlのジクロロメタン中の5.5gの2,3,6−トリフルオロフェニルアセチルクロリドを0℃でゆっくりと滴下添加した。次に混合物を室温で一晩撹拌し、塩化アンモニウム溶液を加えた。有機相を分離し、乾燥し、濃縮した。カラムクロマトグラフィーにより精製によって、6.2gの2,3,6−トリフルオロフェニル酢酸1−メチルヒドラジドを得た。
例1:395mlのピルビン酸エチルを、1gの2,3,6−トリフルオロフェニル酢酸1−メチルヒドラジドに加え、10mlのエタノールに溶解した。反応混合物を環流下で6時間加熱し、次に減圧下で濃縮し、カラムクロマトグラフィー(シリカゲル、移動相シクロヘキサン/酢酸エチル4:1)により精製した。このことによって、1.03gの表95の化合物1を得た。
a)散粉剤は、10重量部の式(I)の化合物および/またはこの塩ならびに不活性物質として90重量部のタルクを混合し、混合物をハンマーミルで微粉砕することによって得られる。
75重量部の式(I)の化合物および/またはこの塩、
10重量部のリグノスルホン酸カルシウム、
5重量部のラウリル硫酸ナトリウム、
3重量部のポリビニルアルコール、および
7重量部のカオリン
を混合し、
混合物をピンディスクミルで粉砕し、流動層において造粒液として水を噴霧することにより粉末を造粒する
ことによって得られる。
25重量部の式(I)の化合物、
5重量部のナトリウム2,2’−ジナフチルメタン−6,6’−ジスルホネート、
2重量部のナトリウムオレオイルメチルタウレート、
1重量部のポリビニルアルコール、
17重量部の炭酸カルシウム、および
50重量部の水を、
コロイドミルにおいて均一化および前微粉砕し、次に混合物をビードミルで粉砕し、得られた懸濁物を、単一流体ノズルを使用して、噴霧塔において霧化および乾燥することによっても得られる。
1.有害植物に対する出芽前除草効果
単子葉または双子葉の雑草または作物植物の種子を、木部繊維ポットの砂壌土に入れ、土壌で覆う。次に水和剤(WP)または乳剤(EC)の形態で製剤された本発明の化合物を、0.2%の湿潤剤を加えた水性懸濁剤または乳濁剤の形態により、水施用量の600から800l/ha(換算)で覆土の表面に施用する。処理後、ポットを温室の中に置き、試験植物を良好な成長条件下に保持する。試験植物への損傷を、実験期間の3週間が経過した後、未処理対照と比較して目視により評価する(除草活性率(%):100%活性=植物の枯死、0%活性=対照植物と同じ)。ここで、例えば化合物番号I−1−c−4およびII−1−c−7は、320g/haの施用量により、エキノクロア・クルス・ガッリ(Echinochloa crus galli)、ステッラリア・メディア(Stellaria media)およびウェロニカ・ペルシカ(Veronica persica)に対してそれぞれ少なくとも90%の活性を示す。
単子葉または双子葉の雑草または作物植物の種子を、木部繊維ポットの砂壌土に入れ、土壌で覆い、温室において良好な成長条件下で成長させる。播種の2から3週間後、試験植物を第一葉期で処理する。次に水和剤(WP)または乳剤(EC)の形態で製剤された本発明の化合物を、0.2%の湿潤剤を加えた水性懸濁剤または乳濁剤の形態により、水施用量の600から800l/ha(換算)で緑色植物部分に噴霧する。試験植物を最適成長条件下で温室内におよそ3週間放置した後、調合剤の活性を未処理対照と比較して目視により評価する(除草活性率(%):100%活性=植物の枯死、0%活性=対照植物と同じ)。ここで、例えば、化合物番号I−1−c−4は、80g/haの施用量により、アブティロン・テオプラスティ(Abutilon theophrasti)、アロペクルス・ミュオスロイデス(Alopecurus myosuroides)、アウェナ・ファトゥア(Avena fatua)、エキノクロア・クルス・ガッリ(Echinochloa crus galli)、ロリウム・ムルティフロルム(Lolium multiflorum)、セタリア・ウィリディス(Setaria viridis)およびウェロニカ・ペルシカ(Veronica persica)に対して少なくとも80%の活性を示す。
例A
ミュズス(Myzus)試験(MYZUPE噴霧処理)
溶媒:78.0重量部のアセトン
1.5重量部のジメチルホルムアミド
乳化剤:0.5重量部のアルキルアリールポリグリコールエーテル
活性化合物の適切な調合剤を製造するために、1重量部の活性化合物を記述量の溶媒および乳化剤と混合し、濃縮物を乳化剤含有水で希釈して、所望の濃度にする。全期のモモアカアブラムシ(ミュズス・ペルシカエ(Myzus persicae))が発生しているハクサイ(ブラッシカ・ペキネンシス(Brassica pekinensis))の花盤に、所望の濃度の活性化合物の調合剤を噴霧する。所望の時間後、効果(%)を決定する。100%は、全てのアブラムシが死滅したことを意味し、0%は死滅したアブラムシがいないことを意味する。この試験において、例えば化合物番号I−1−a−4は、500g/haの施用量で少なくとも80%の活性を示す。
スポドプテラ・フルギペルダ(Spodoptera frugiperda)試験(SPODFR噴霧処理)
溶媒:78.0重量部のアセトン
1.5重量部のジメチルホルムアミド
乳化剤:0.5重量部のアルキルアリールポリグリコールエーテル
活性化合物の適切な調合剤を製造するために、1重量部の活性化合物を記述量の溶媒および乳化剤と混合し、濃縮物を乳化剤含有水で希釈して、所望の濃度にする。トウモロコシ(ゼア・マユス(Zea mays)の花盤に所望の濃度の活性化合物の調合剤を噴霧し、乾燥した後、ヨトウムシ(スポドプテラ・フルギペルダ(Spodoptera frugiperda))の毛虫を生息させる。所望の時間後、効果(%)を決定する。100%は、全ての毛虫が死滅したことを意味し、0%は死滅した毛虫がいないことを意味する。この試験において、例えば化合物番号I−1−a−9は、500g/haの施用量で少なくとも80%の活性を示す。
メロイドギュネ・インコグニタ(Meloidogyne incognita)試験(MELGIN)
溶媒:78.0重量部のアセトン
1.5重量部のジメチルホルムアミド
乳化剤:0.5重量部のアルキルアリールポリグリコールエーテル
活性化合物の適切な調合剤を製造するために、1重量部の活性化合物を記述量の溶媒および乳化剤と混合し、濃縮物を水で希釈して、所望の濃度にする。容器を、砂、活性化合物の溶液、メロイドギュネ・インコグニタ(Meloidogyne incognita)の卵/幼虫懸濁物およびレタス種子で充填する。レタス種子は発芽し、植物は成長する。根において、こぶが形成される。所望の時間の後、殺線虫活性をこぶの形成により%で決定する。100%は、こぶの形成がないことを意味し、0%は、処理植物におけるこぶの数が未処理対照に匹敵することを意味する。この試験において、例えば化合物番号I−1−a−9およびI−1−a−10は、20ppmの施用量により少なくとも80%の効能を示す。
Claims (15)
- 式(I)の4−フェニルピリダジノンまたはその塩
Aは、それぞれの場合において互いに独立して、水素、(C3−C6)シクロアルキルまたは(C1−C6)アルキル(ハロゲン、(C3−C6)シクロアルキル、フェニルおよびハロフェニルからなる群からのn個の基で置換されている。)であり;
Bは、互いに独立して、(C3−C6)シクロアルキルまたは(C1−C6)アルキル(ハロゲン、(C3−C6)シクロアルキル、フェニルおよびハロフェニルからなる群からのn個の基で置換されている。)であり;
mは、0、1、2または3であり;
nは、0、1、2または3であるが、但し、mおよびnは、両方とも0であることはなく;
Gは、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7、EまたはR8であり;
Eは、金属イオン等価物またはアンモニウムイオンであり;
Lは、酸素または硫黄であり;
Mは、酸素または硫黄であり;
R1は、それぞれn個のハロゲン原子で置換されている、(C1−C6)アルキル、(C2−C6)アルケニル、(C1−C4)アルコキシ−(C1−C6)アルキル、ジ−(C1−C4)アルコキシ−(C1−C6)アルキルまたは(C1−C4)アルキルチオ−(C1−C6)アルキル、
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、3から5個の炭素原子ならびに酸素、硫黄および窒素からなる群からの1から3個のヘテロ原子からなる完全飽和の3員から6員の環、
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、(C3−C6)シクロアルキル、フェニル、フェニル−(C1−C4)アルキル、ヘテロアリール、フェノキシ−(C1−C4)アルキルまたはヘテロアリールオキシ−(C1−C4)アルキルであり;
R2は、それぞれn個のハロゲン原子で置換されている、(C1−C6)アルキル、(C2−C6)アルケニル、(C1−C4)アルコキシ−(C1−C6)アルキルもしくはジ−(C1−C4)アルコキシ−(C1−C6)アルキル、または
(C3−C6)シクロアルキル、フェニルもしくはベンジルであり、それぞれ、ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R3、R4およびR5は、それぞれ互いに独立して、(C1−C6)アルキル(n個のハロゲン原子で置換されている。)、(C1−C4)アルコキシ、N−(C1−C6)アルキルアミノ、N,N−ジ−(C1−C6)アルキルアミノ、(C1−C4)アルキルチオ、(C2−C4)アルケニルもしくは(C3−C6)シクロアルキルチオである、または
ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている、フェニル、ベンジル、フェノキシもしくはフェニルチオであり;
R6およびR7は、それぞれ互いに独立して、水素である、
(C1−C6)アルキル(n個のハロゲン原子で置換されている。)、(C3−C6)シクロアルキル、(C2−C6)アルケニル、(C1−C6)アルコキシもしくは(C1−C4)アルコキシ−(C1−C6)アルキルである、
フェニルもしくはベンジルであり、それぞれ、ハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されている;または
R6およびR7は、それらが結合している窒素原子と一緒になって、2から5個の炭素原子および0もしくは1個の酸素もしくは硫黄原子を含有する、3員から6員の環を形成し;
a)Xは、水素、(C1−C6)アルキルもしくは(C3−C6)シクロアルキルであり;
Yは、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、(C1−C6)アルコキシである、もしくはn個のハロゲン原子で置換されているフェニルであり;
Zは、水素、ハロゲン、シアノ、ニトロ、(C1−C6)アルキル、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキルである、もしくはn個のハロゲン原子で置換されているフェニルである;または
b)Xは、ハロゲン、シアノ、ニトロである、もしくは(C1−C6)アルキル、(C3−C6)シクロアルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれ、n個のハロゲン原子で置換されており;
YおよびZは、それぞれ互いに独立して、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、もしくは(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されている。]。 - Aが、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C6)アルキル、ベンジル、ハロフェニル−(C1−C6)アルキルである、またはn個のハロゲン原子で置換されている(C1−C6)アルキルであり;
Bが、(C3−C6)シクロアルキル、(C3−C6)シクロアルキル−(C1−C6)アルキル、ベンジル、ハロフェニル−(C1−C6)アルキルである、またはn個のハロゲン原子で置換されている(C1−C6)アルキルであり;
mが、0、1、2または3であり;
nが、0、1、2または3であるが、但し、mおよびnが、両方とも0であることはなく;
Gが、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7またはEであり;
Eが、Na+、K+、(Mg2+)1/2、(Ca2+)1/2、R13R14R15R16N+またはNH4 +であり;
R13、R14、R15およびR16が、互いに独立して、(C1−C6)アルキルまたはベンジルであり;
Lが、酸素であり;
Mが、酸素であり;
R1が、n個のハロゲン原子で置換されている(C1−C6)アルキルである、または(C3−C6)シクロアルキル、フェニルもしくはフェニル−(C1−C4)アルキルであり、それぞれハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R2が、n個のハロゲン原子で置換されている(C1−C6)アルキルである、または(C3−C6)シクロアルキル、フェニルもしくはベンジルであり、それぞれハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されており;
R3、R4およびR5が、それぞれ互いに独立して、n個のハロゲン原子で置換されている(C1−C6)アルキルである、またはハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されているフェニルもしくはベンジルであり;
R6およびR7が、それぞれ互いに独立して、水素、n個のハロゲン原子で置換されている(C1−C6)アルキルである、またはハロゲン、(C1−C4)アルキルおよび(C1−C4)アルコキシからなる群からのn個の基で置換されているフェニルもしくはベンジルであり;
a)Xが、水素、メチル、エチルまたはシクロプロピルであり;
Yが、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、(C1−C6)アルコキシ、もしくはn個のハロゲン原子で置換されているフェニルであり;
Zが、水素、ハロゲン、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C3−C6)シクロアルキル、もしくはn個のハロゲン原子で置換されているフェニルである;または
b)Xが、ハロゲン、シアノ、ニトロ、ハロ−(C1−C6)アルキル、ハロ−(C1−C6)アルコキシ、(C1−C6)アルコキシもしくは(C3−C6)シクロアルキルであり;
Yが、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されており;
Zが、水素、ハロゲン、シアノ、ニトロ、(C3−C6)シクロアルキルである、もしくは(C1−C6)アルキル、(C1−C6)アルコキシもしくはフェニルであり、それぞれn個のハロゲン原子で置換されている、
請求項1に記載の4−フェニルピリダジノン。 - Aが、シクロプロピル、シクロプロピルメチル、ベンジル、2−クロロフェニルメチル、3−クロロフェニルメチルまたは4−クロロフェニルメチルであり;
Bが、水素、2,2−ジフルオロエチル、2,2,2−トリフルオロエチル、シクロプロピル、シクロプロピルメチル、ベンジル、2−クロロフェニルメチル、3−クロロフェニルメチルまたは4−クロロフェニルメチルであり;
Gが、水素、C(=O)R1、C(=L)MR2、SO2R3、P(=L)R4R5、C(=L)NR6R7、EまたはR8であり;
Eが、Na+、K+、(Mg2+)1/2、(Ca2+)1/2、(CH3)4N+またはNH4 +であり;
Lが、酸素であり;
Mが、酸素であり;
R1が、(C1−C6)アルキルまたは(C3−C6)シクロアルキルであり;
R2が、(C1−C6)アルキル、(C3−C6)シクロアルキルまたはベンジルであり;
R3、R4およびR5が、それぞれ互いに独立して、(C1−C6)アルキル、フェニルまたはベンジルであり;
R6およびR7が、それぞれ互いに独立して、水素、(C1−C6)アルキル、フェニルまたはベンジルであり;
a)Xが、水素、メチルもしくはエチルであり;
Yが、フッ素、臭素、塩素、ヨウ素、シアノ、ニトロ、シクロプロピル、メトキシ、エトキシ、トリフルオロメチルもしくはトリフルオロメトキシ、フェニルもしくはハロフェニルであり;
Zが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチルもしくはシクロプロピルである;または
b)Xが、フッ素、臭素、塩素、ヨウ素、シアノ、ニトロ、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシもしくはシクロプロピルであり;
Yが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシもしくはシクロプロピルであり;
Zが、水素、フッ素、臭素、塩素、ヨウ素、メチル、エチル、メトキシ、エトキシ、トリフルオロメチル、トリフルオロメトキシ、シクロプロピル、クロロフェニルもしくはフルオロフェニルである、
請求項1または2に記載の4−フェニルピリダジノン。 - 請求項1から3のいずれか1項に記載の式(I)の少なくとも1つの4−フェニルピリダジノンの有効量を含む除草組成物。
- 製剤助剤との混合物としての、請求項4に記載の除草組成物。
- 殺虫剤、殺ダニ剤、除草剤、殺真菌剤、毒性緩和剤および成長調節剤からなる群の少なくとも1つのさらなる殺有害生物剤として活性な化合物を含む、請求項4または5に記載の除草組成物。
- 毒性緩和剤を含む、請求項6に記載の除草組成物。
- さらなる除草剤を含む、請求項6または7に記載の除草組成物。
- 不要な植物を防除する方法であって、請求項1から3のいずれか1項に記載の式(I)の少なくとも1つの4−フェニルピリダジノンまたは請求項4から8のいずれか1項に記載の除草組成物の有効量を、植物または不要な植物が成長している場所に施用することを含む方法。
- 請求項1から3のいずれか1項に記載の式(I)の4−フェニルピリダジノンまたは請求項4から8のいずれか1項に記載の除草組成物の、不要な植物を防除するための使用。
- 式(I)の4−フェニルピリダジノンが、有用植物の作物において不要な植物を防除するために使用される、請求項10に記載の使用。
- 有用植物がトランスジェニック有用植物である、請求項11に記載の使用。
- 請求項1から3のいずれか1項に記載の式(I)の4−フェニルピリダジノンの殺虫剤としての使用。
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EP08022104.7 | 2008-12-19 | ||
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- 2009-12-12 BR BRPI0923035A patent/BRPI0923035A2/pt not_active IP Right Cessation
- 2009-12-12 CN CN2009801572630A patent/CN102325757A/zh active Pending
- 2009-12-12 WO PCT/EP2009/008908 patent/WO2010069525A1/de active Application Filing
- 2009-12-12 WO PCT/EP2009/008906 patent/WO2010078912A1/de active Application Filing
- 2009-12-14 US US12/637,025 patent/US20110003692A1/en not_active Abandoned
- 2009-12-15 US US12/638,105 patent/US8188008B2/en active Active
- 2009-12-15 US US12/638,180 patent/US8242055B2/en active Active
- 2009-12-17 AR ARP090104941A patent/AR075673A1/es not_active Application Discontinuation
- 2009-12-17 AR ARP090104943A patent/AR074774A1/es unknown
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JPH11140055A (ja) * | 1997-09-01 | 1999-05-25 | Nissan Chem Ind Ltd | 6−ハロアルキル−3−置換フェニル−2(1h)−ピリジノン誘導体及び除草剤 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014119770A1 (ja) * | 2013-01-30 | 2014-08-07 | 住友化学株式会社 | ピリダジノン化合物及びそれを含有する除草剤 |
WO2023189602A1 (ja) * | 2022-03-30 | 2023-10-05 | 石原産業株式会社 | ピリダジノン系化合物又はその塩及びそれらを含有する有害生物防除剤 |
Also Published As
Publication number | Publication date |
---|---|
CN102325757A (zh) | 2012-01-18 |
WO2010078912A1 (de) | 2010-07-15 |
EP2204366A1 (de) | 2010-07-07 |
CA2747638A1 (en) | 2010-07-15 |
WO2010078912A8 (de) | 2011-07-14 |
JP2012512209A (ja) | 2012-05-31 |
US8242055B2 (en) | 2012-08-14 |
US8188008B2 (en) | 2012-05-29 |
US20100184602A1 (en) | 2010-07-22 |
CN105732513A (zh) | 2016-07-06 |
EP2379509B1 (de) | 2016-02-17 |
CN102325756A (zh) | 2012-01-18 |
AU2009336854A8 (en) | 2011-12-01 |
EP2379508B1 (de) | 2014-06-04 |
US20100173775A1 (en) | 2010-07-08 |
AU2009328607A1 (en) | 2011-07-07 |
JP5651601B2 (ja) | 2015-01-14 |
WO2010069526A1 (de) | 2010-06-24 |
EP2379509A1 (de) | 2011-10-26 |
AR074773A1 (es) | 2011-02-09 |
AU2009336854A1 (en) | 2011-07-21 |
JP5651602B2 (ja) | 2015-01-14 |
EP2379508A1 (de) | 2011-10-26 |
AR074774A1 (es) | 2011-02-09 |
AR075673A1 (es) | 2011-04-20 |
BRPI0922428B1 (pt) | 2018-07-10 |
US20110003692A1 (en) | 2011-01-06 |
BRPI0923035A2 (pt) | 2018-10-16 |
WO2010069525A1 (de) | 2010-06-24 |
BRPI0922428A2 (pt) | 2015-08-11 |
CN106928148A (zh) | 2017-07-07 |
CA2747639A1 (en) | 2010-06-24 |
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