KR101755145B1 - 아릴옥시우레아 화합물 및 유해 생물 방제제 - Google Patents
아릴옥시우레아 화합물 및 유해 생물 방제제 Download PDFInfo
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- KR101755145B1 KR101755145B1 KR1020157033140A KR20157033140A KR101755145B1 KR 101755145 B1 KR101755145 B1 KR 101755145B1 KR 1020157033140 A KR1020157033140 A KR 1020157033140A KR 20157033140 A KR20157033140 A KR 20157033140A KR 101755145 B1 KR101755145 B1 KR 101755145B1
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- unsubstituted
- alkyl group
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- alkyl
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- 125000003729 nucleotide group Chemical group 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
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- IVMHDOBGNQOUHO-UHFFFAOYSA-N oxathiane Chemical group C1CCSOC1 IVMHDOBGNQOUHO-UHFFFAOYSA-N 0.000 description 1
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
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- IHGKZTZBFNNHIJ-UHFFFAOYSA-N phenyl n-(3-bromo-5-chlorophenoxy)carbamate Chemical compound ClC1=CC(Br)=CC(ONC(=O)OC=2C=CC=CC=2)=C1 IHGKZTZBFNNHIJ-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
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- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 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
- 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
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 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
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- YGBMMMOLNODPBP-GWGZPXPZSA-N s-ethyl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate Chemical compound CCSC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)(C)OC YGBMMMOLNODPBP-GWGZPXPZSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-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
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 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
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 229960005199 tetramethrin Drugs 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
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group 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
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 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
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-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
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- 238000004383 yellowing Methods 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/66—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to halogen atoms or to nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to 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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
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Abstract
Description
본 발명은 신규한 유해 생물 방제제에 관한 것이다. 보다 상세하게는, 본 발명은 우수한 살진드기 활성 및/또는 살균 활성을 갖고, 특성과 안전성이 우수하면서, 또한 공업적으로 유리하게 합성할 수 있는 아릴옥시우레아 화합물 그리고 이것을 유효 성분으로 하는 살진드기제 및/또는 살균제에 관한 것이다.
본원은 2010년 10월 12일에 일본에 출원된 일본 특허출원 2010-229617호에 기초하여 우선권을 주장하고, 그 내용을 여기에 원용한다.
본 발명의 화합물에 구조상 관련되는 화합물로서, 특허문헌 1 ∼ 5 에는 식 (A) ∼ 식 (E) 로 나타내는 화합물이 개시되어 있다.
[화학식 1]
상기 식 중, R1 은 C1∼6 알킬기 등을 나타낸다.
R2 는 수소 원자 등을 나타낸다.
[화학식 2]
상기 식 중, X1 은 수소 원자, 염소 원자 등을 나타낸다.
Y1 은 수소 원자, 염소 원자 등을 나타낸다.
R3 은 페닐기 등을 나타낸다.
R4 는 수소 원자, 저급 알킬기 등을 나타낸다.
R5 는 수소 원자 등을 나타낸다.
A 는 탄소 원자 또는 질소 원자를 나타낸다.
[화학식 3]
상기 식 중, X2 는 수소 원자, 할로겐 원자, C1∼8 알킬기 등을 나타낸다.
Y2 는 수소 원자, 할로겐 원자, C1∼8 알킬기 등을 나타낸다.
R6 은 페닐기, 시아노기, C1∼4 알킬기 등을 나타낸다.
R7 은 수소 원자, C1∼4 알킬기 등을 나타낸다.
R8 및 R9 는 독립적으로 수소 원자, C1∼3 알킬기 등을 나타낸다.
R10 은 할로겐 원자, C1∼4 알킬기를 나타낸다.
[화학식 4]
상기 식 중, X3 은 염소 원자, 브롬 원자, 또는 메틸기를 나타낸다.
Y3 은 염소 원자, 브롬 원자, 또는 메틸기를 나타낸다.
R11 은 에틸기, n-프로필기를 나타낸다.
R12 는 에틸기를 나타낸다.
[화학식 5]
상기 식 중, X4 및 Y4 중의 일방은 질소 원자 또는 질소 산화물을 나타내고, 다른 일방은 CR (R 은 수소 원자, 할로겐 원자 등을 나타낸다) 을 나타내거나, 또는, X4 및 Y4 의 양방이 질소 원자를 나타낸다.
Z1 은 수소 원자, 할로겐 원자 등을 나타낸다.
R13 은 알킬기, 알케닐기 등을 나타낸다.
R14 는 벤질 부분의 페닐 고리가 임의적으로 C1∼4 알콕시기로 치환되어 있는 벤질옥시메틸기 등을 나타낸다.
R15 및 R16 은 양방이 모두 수소 원자는 아니고, 양방이 수소 원자 이외인 경우 그들의 조합한 탄소 원자 합계가 4 를 초과하지 않는 것을 조건으로 하여, 독립적으로 수소 원자, C1∼3 알킬기 등을 나타낸다.
R17 은 C1∼4 알킬, C3∼6 시클로알킬 등을 나타낸다.
본 발명은 신규한 유해 생물 방제제, 그 중에서도, 우수한 살진드기 활성 및/또는 살균 활성을 갖고, 특성과 안전성이 우수하며, 또한 공업적으로 유리하게 합성할 수 있는 아릴옥시우레아 화합물 또는 그 염 그리고 이것을 유효 성분으로서 함유하는 살진드기제 및/또는 살균제를 제공하는 것을 과제로 한다.
본 발명자들은 상기 과제를 해결하기 위해 예의 검토한 결과, 특정한 구조를 갖는 아릴옥시우레아 화합물 또는 그 염은 우수한 살진드기 활성 및/또는 살균 활성을 가지며, 또한 양호한 특성과 높은 안전성을 나타내는 살진드기제 및/또는 살균제의 유효 성분이 될 수 있음을 알아내었다.
본 발명은 이러한 지견에 기초하여 완성하기에 이른 것이다.
즉, 본 발명은 이하의 것을 포함한다.
(1) 식 (I) 로 나타내는 아릴옥시우레아 화합물 또는 그 염.
[화학식 6]
상기 식 (I) 중, Cy 는 C6∼10 아릴기, 또는 헤테로아릴기를 나타낸다.
X 는 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 수산기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시기, 아미노기, 비치환의 혹은 치환기를 갖는 C1∼6 알킬아미노기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C1∼6 알킬술포닐기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시술포닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 혹은 치환기를 갖는 하이드록시이미노 C1∼6 알킬기, 니트로기, 시아노기, 또는 할로겐 원자를 나타낸다.
n 은 Cy 상의 X 의 개수를 나타내며 또한 0 ∼ 5 중 어느 정수이다. n 이 2 이상일 때, X 는 서로 동일하거나 상이해도 된다. 또한, n 이 2 이상일 때, X 는 하나가 되어 결합하는 탄소 원자 또는 질소 원자와 함께 고리를 형성해도 된다.
R1 은 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 또는 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기를 나타낸다.
Q 는 식 (II), 식 (III), 또는 식 (IV) 로 나타내는 기를 나타낸다.
[화학식 7]
상기 식 (II) 중, * 는 결합 위치를 나타낸다. R2 는 수소 원자, 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 또는, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기를 나타내고, R1 과 R2 는 하나가 되어 비치환의 혹은 치환기를 갖는 C2∼4 알킬렌기를 형성해도 된다.
R3 및 R4 는 각각 독립적으로 수소 원자, 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 또는 시아노기를 나타낸다. 여기서, R3 과 R4 는 하나가 되어 결합하는 탄소 원자와 함께 고리를 형성해도 된다.
R5 는 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 카르복실기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐옥시카르보닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐옥시카르보닐기, 비치환의 혹은 치환기를 갖는 아미노카르보닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 혹은 치환기를 갖는 하이드록시이미노 C1∼6 알킬기, 또는 시아노기를 나타낸다.
[화학식 8]
상기 식 (III) 중, * 는 결합 위치를 나타낸다. R6 및 R7 은 각각 독립적으로 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 또는 비치환의 혹은 치환기를 갖는 헤테로아릴기를 나타낸다. 여기서, R6 과 R7 은 하나가 되어 결합하는 황 원자와 함께 고리를 형성해도 된다.
[화학식 9]
상기 식 (IV) 중, * 는 결합 위치를 나타낸다. R2 는 상기와 동일한 의미를 나타낸다. R8 은 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 또는 비치환의 혹은 치환기를 갖는 헤테로아릴기를 나타낸다.
Z 는 산소 원자 또는 황 원자를 나타낸다.
(2) 상기 식 (I) 로 나타내는 아릴옥시우레아 화합물이 식 (V) 로 나타내는 아릴옥시우레아 화합물 또는 그 염.
[화학식 10]
상기 식 (V) 중, R1 ∼ R5, X, n, 및 Z 는 상기와 동일한 의미를 나타낸다.
(3) 상기 (1) 또는 (2) 에 기재된 아릴옥시우레아 화합물 또는 그 염에서 선택되는 적어도 1 종을 유효 성분으로서 함유하는 유해 생물 방제제.
(4) 상기 (1) 또는 (2) 에 기재된 아릴옥시우레아 화합물 또는 그 염에서 선택되는 적어도 1 종을 유효 성분으로서 함유하는 살진드기제.
(5) 상기 (1) 또는 (2) 에 기재된 아릴옥시우레아 화합물 또는 그 염에서 선택되는 적어도 1 종을 유효 성분으로서 함유하는 살균제.
본 발명의 아릴옥시우레아 화합물 또는 그 염은 농작물이나 위생면에서 문제가 되는 유해 생물을 방제할 수 있다. 특히, 진드기류 및/또는 식물 병원균류를 효과적으로 방제할 수 있다.
[아릴옥시우레아 화합물]
본 발명의 아릴옥시우레아 화합물은 하기 식 (I) 로 나타내는 화합물이다.
[화학식 11]
[치환기]
본 명세서에 있어서 「비치환의」란 용어는 모핵이 되는 기만인 것을 의미한다. 또한, 본 명세서에 있어서 「치환기를 갖는다」라는 기재가 없이 모핵이 되는 기의 명칭만으로 기재하고 있을 때에는, 별도의 언급이 없는 한 「비치환의」 의미이다.
한편, 「치환기를 갖는다」란 용어는 모핵이 되는 기의 어떠한 수소 원자가 모핵과 동일하거나 또는 상이한 구조의 기로 치환되어 있는 것을 의미한다. 따라서, 「치환기」는 모핵이 되는 기에 결합한 다른 기이다. 치환기는 1 개이어도 되고, 2 개 이상이어도 된다. 2 개 이상의 치환기는 동일해도 되고, 상이한 것이어도 된다.
「C1∼6」등의 용어는 모핵이 되는 기의 탄소 원자수가 1 ∼ 6 개 등인 것을 표현하고 있다. 이 탄소 원자수에는, 치환기 중에 존재하는 탄소 원자의 수를 포함하지 않는다. 예를 들어, 치환기로서 에톡시기를 갖는 부틸기는 C2 알콕시 C4 알킬기로 분류한다.
「치환기」는 화학적으로 허용되고, 본 발명의 효과를 갖는 한에 있어서 특별히 제한되지 않는다.
「치환기」로 될 수 있는 기로는, 구체적으로는 이하의 기를 예시할 수 있다.
불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자 ;
메틸기, 에틸기, n-프로필기, i-프로필기, n-부틸기, s-부틸기, i-부틸기, t-부틸기, n-펜틸기, n-헥실기 등의 C1∼6 알킬기 ;
시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기 등의 C3∼8 시클로알킬기 ;
비닐기, 1-프로페닐기, 2-프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-메틸-2-프로페닐기, 2-메틸-2-프로페닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 4-펜테닐기, 1-메틸-2-부테닐기, 2-메틸-2-부테닐기, 1-헥세닐기, 2-헥세닐기, 3-헥세닐기, 4-헥세닐기, 5-헥세닐기 등의 C2∼6 알케닐기 ;
2-시클로프로페닐기, 2-시클로펜테닐기, 3-시클로헥세닐기, 4-시클로옥테닐기 등의 C3∼8 시클로알케닐기 ;
에티닐기, 1-프로피닐기, 2-프로피닐기, 1-부티닐기, 2-부티닐기, 3-부티닐기, 1-메틸-2-프로피닐기, 2-메틸-3-부티닐기, 1-펜티닐기, 2-펜티닐기, 3-펜티닐기, 4-펜티닐기, 1-메틸-2-부티닐기, 2-메틸-3-펜티닐기, 1-헥시닐기, 1,1-디메틸-2-부티닐기 등의 C2∼6 알키닐기 ;
메톡시기, 에톡시기, n-프로폭시기, i-프로폭시기, n-부톡시기, s-부톡시기, i-부톡시기, t-부톡시기 등의 C1∼6 알콕시기 ;
비닐옥시기, 알릴옥시기, 프로페닐옥시기, 부테닐옥시기 등의 C2∼6 알케닐옥시기 ;
에티닐옥시기, 프로파르길옥시기 등의 C2∼6 알키닐옥시기 ;
페닐기, 나프틸기 등의 C6∼10 아릴기 ;
페녹시기, 1-나프톡시기 등의 C6∼10 아릴옥시기 ;
벤질기, 페네틸기 등의 C7∼11 아르알킬기 ;
벤질옥시기, 페네틸옥시기 등의 C7∼11 아르알킬옥시기 ;
포르밀기, 아세틸기, 프로피오닐기, 벤조일기, 시클로헥실카르보닐기 등의 C1∼7 아실기 ;
포르밀옥시기, 아세틸옥시기, 프로피오닐옥시기, 벤조일옥시기, 시클로헥실카르보닐옥시기 등의 C1∼7 아실옥시기 ;
메톡시카르보닐기, 에톡시카르보닐기, n-프로폭시카르보닐기, i-프로폭시카르보닐기, n-부톡시카르보닐기, t-부톡시카르보닐기 등의 C1∼6 알콕시카르보닐기 ;
카르복실기 ;
수산기 ;
클로로메틸기, 클로로에틸기, 트리플루오로메틸기, 1,2-디클로로-n-프로필기, 1-플루오로-n-부틸기, 퍼플루오로-n-펜틸기 등의 C1∼6 할로알킬기 ;
2-클로로-1-프로페닐기, 2-플루오로-1-부테닐기 등의 C2∼6 할로알케닐기 ;
4,4-디클로로-1-부티닐기, 4-플루오로-1-펜티닐기, 5-브로모-2-펜티닐기 등의 C2∼6 할로알키닐기 ;
2-클로로-n-프로폭시기, 2,3-디클로로부톡시기 등의 C1∼6 할로알콕시기 ;
2-클로로프로페닐옥시기, 3-브로모부테닐옥시기 등의 C2∼6 할로알케닐옥시기 ;
4-클로로페닐기, 4-플루오로페닐기, 2,4-디클로로페닐기 등의 C6∼10 할로아릴기 ;
4-플루오로페닐옥시기, 4-클로로-1-나프톡시기 등의 C6∼10 할로아릴옥시기 ;
클로로아세틸기, 트리플루오로아세틸기, 트리클로로아세틸기, 4-클로로벤조일기 등의 할로겐 치환 C1∼7 아실기 ;
시아노기 ; 니트로기 ; 아미노기 ;
메틸아미노기, 디메틸아미노기, 디에틸아미노기 등의 C1∼6 알킬아미노기 ;
아닐리노기, 나프틸아미노기 등의 C6∼10 아릴아미노기 ;
벤질아미노기, 페닐에틸아미노기 등의 C7∼11 아르알킬아미노기 ;
포르밀아미노기, 아세틸아미노기, 프로파노일아미노기, 부티릴아미노기, i-프로필카르보닐아미노기, 벤조일아미노기 등의 C1∼7 아실아미노기 ;
메톡시카르보닐아미노기, 에톡시카르보닐아미노기, n-프로폭시카르보닐아미노기, i-프로폭시카르보닐아미노기 등의 C1∼6 알콕시카르보닐아미노기 ;
아미노카르보닐기, 디메틸아미노카르보닐기, 페닐아미노카르보닐기, N-페닐-N-메틸아미노카르보닐기 등의 비치환의 혹은 치환기를 갖는 아미노카르보닐기 ;
이미노메틸기, (1-이미노)에틸기, (1-이미노)-n-프로필기 등의 이미노 C1∼6 알킬기 ;
하이드록시이미노메틸기, (1-하이드록시이미노)에틸기, (1-하이드록시이미노)프로필기 등의 하이드록시이미노 C1∼6 알킬기 ;
메르캅토기 ;
메틸티오기, 에틸티오기, n-프로필티오기, i-프로필티오기, n-부틸티오기, i-부틸티오기, s-부틸티오기, t-부틸티오기 등의 C1∼6 알킬티오기 ;
비닐티오기, 알릴티오기 등의 C2∼6 알케닐티오기 ;
에티닐티오기, 프로파르길티오기 등의 C2∼6 알키닐티오기 ;
페닐티오기, 나프틸티오기 등의 C6∼10 아릴티오기 ;
티아졸릴티오기, 피리딜티오기 등의 헤테로아릴티오기 ;
벤질티오기, 페네틸티오기 등의 C7∼11 아르알킬티오기 ;
(메틸티오)카르보닐기, (에틸티오)카르보닐기, (n-프로필티오)카르보닐기, (i-프로필티오)카르보닐기, (n-부틸티오)카르보닐기, (i-부틸티오)카르보닐기, (s-부틸티오)카르보닐기, (t-부틸티오)카르보닐기 등의 (C1∼6 알킬티오)카르보닐기 ;
메틸술피닐기, 에틸술피닐기, t-부틸술피닐기 등의 C1∼6 알킬술피닐기 ;
알릴술피닐기 등의 C2∼6 알케닐술피닐기 ;
프로파르길술피닐기 등의 C2∼6 알키닐술피닐기 ;
페닐술피닐기 등의 C6∼10 아릴술피닐기 ;
티아졸릴술피닐기, 피리딜술피닐기 등의 헤테로아릴술피닐기 ;
벤질술피닐기, 페네틸술피닐기 등의 C7∼11 아르알킬술피닐기 ;
메틸술포닐기, 에틸술포닐기, t-부틸술포닐기 등의 C1∼6 알킬술포닐기 ;
알릴술포닐기 등의 C2∼6 알케닐술포닐기 ;
프로파르길술포닐기 등의 C2∼6 알키닐술포닐기 ;
페닐술포닐기 등의 C6∼10 아릴술포닐기 ;
티아졸릴술포닐기, 피리딜술포닐기 등의 헤테로아릴술포닐기 ;
벤질술포닐기, 페네틸술포닐기 등의 C7∼11 아르알킬술포닐기 ;
피롤릴기, 푸릴기, 티에닐기, 이미다졸릴기, 피라졸릴기, 옥사졸릴기, 이소옥사졸릴기, 티아졸릴기, 이소티아졸릴기, 트리아졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 테트라졸릴기 등의 5 원자 고리의 헤테로아릴기 ;
피리딜기, 피라지닐기, 피리미디닐기, 피리다지닐기, 트리아지닐기 등의 6 원자 고리의 헤테로아릴기 ;
인돌릴기, 벤조푸릴기, 벤조티에닐기, 벤조이미다졸릴기, 벤조옥사졸릴기, 벤조티아졸릴기, 퀴놀릴기, 이소퀴놀릴기, 퀴녹살리닐기 등의 축합 고리의 헤테로아릴기 ;
아지리디닐기, 옥시라닐기, 피롤리디닐기, 테트라하이드로푸라닐기, 피페리딜기, 피페라지닐기, 모르폴리닐기 등의 포화 헤테로 고리기 ;
트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기 등의 트리 C1∼6 알킬 치환 실릴기 ;
트리페닐실릴기 ;
또한, 이들 「치환기」는 추가로 별도의 「치환기」를 갖는 것이어도 된다.
[Cy]
식 (I) 중, Cy 는 C6∼10 아릴기, 또는 헤테로아릴기를 나타낸다.
「C6∼10 아릴기」는 단고리, 또는 고리끼리 결합된 다고리 중 어느 것이어도 된다. 다고리 아릴기는, 적어도 하나의 고리가 방향 고리이면, 나머지 고리가 포화 지환, 불포화 지환 또는 방향 고리 중 어느 것이어도 된다. C6∼10 아릴기로는, 페닐기, 나프틸기, 아줄레닐기, 인데닐기, 인다닐기, 테트랄리닐기 등을 예시할 수 있다.
「헤테로아릴기」는 고리를 구성하는 원자로서 탄소 원자 이외에 질소 원자, 산소 원자 및 황 원자에서 선택되는 1 ∼ 4 개의 복소 원자를 함유하는 5 ∼ 10 원자의 아릴기이다. 이 경우, 단고리, 또는 고리끼리가 축합된 다고리이어도 된다.
헤테로아릴기로는, 상기의 치환기에서 예시한 5 원자 고리의 헤테로아릴기, 6 원자 고리의 헤테로아릴기, 축합 고리의 헤테로아릴기 등을 들 수 있다.
이들 중, Cy 는 페닐기, 나프틸기, 피리딜기, 피리미디닐기, 피리다지닐기, 퀴놀릴기, 이소퀴놀릴기, 퀴녹살리닐기인 것이 바람직하고, 페닐기인 것이 보다 바람직하다.
[X]
식 (I) 중, X 는 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 수산기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시기, 아미노기, 비치환의 혹은 치환기를 갖는 C1∼6 알킬아미노기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C1∼6 알킬술포닐기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시술포닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 혹은 치환기를 갖는 하이드록시이미노 C1∼6 알킬기, 니트로기, 시아노기, 또는 할로겐 원자를 나타낸다.
n 은 Cy 상의 X 의 개수를 나타내며 또한 0 ∼ 5 중 어느 정수이다. n 이 2 이상일 때, X 는 서로 동일하거나 상이해도 된다. 또한, n 이 2 이상일 때, X 는 하나가 되어 결합하는 탄소 원자 또는 질소 원자와 함께 고리를 형성해도 된다.
X 에 있어서의 「C1∼6 알킬기」는 직사슬이어도 되고, 분기사슬이어도 된다. 알킬기로는, 메틸기, 에틸기, n-프로필기, n-부틸기, n-펜틸기, n-헥실기, i-프로필기, i-부틸기, s-부틸기, t-부틸기, i-펜틸기, 네오펜틸기, 2-메틸부틸기, 2,2-디메틸프로필기, i-헥실기 등을 예시할 수 있다.
「치환기를 갖는 알킬기」로는,
시클로프로필메틸기, 2-시클로프로필에틸기, 시클로펜틸메틸기, 2-시클로헥실에틸기, 2-시클로옥틸에틸기 등의 C3∼8 시클로알킬 C1∼6 알킬기 ;
플루오로메틸기, 클로로메틸기, 브로모메틸기, 디플루오로메틸기, 디클로로메틸기, 디브로모메틸기, 트리플루오로메틸기, 트리클로로메틸기, 트리브로모메틸기, 2,2,2-트리플루오로에틸기, 2,2,2-트리클로로에틸기, 펜타플루오로에틸기, 4-플루오로부틸기, 4-클로로부틸기, 3,3,3-트리플루오로프로필기, 2,2,2-트리플루오로-1-트리플루오로메틸에틸기, 퍼플루오로헥실기, 퍼클로로헥실기, 퍼플루오로옥틸기, 퍼클로로옥틸기, 2,4,6-트리클로로헥실기 등의 C1∼6 할로알킬기 ;
하이드록시메틸기, 2-하이드록시에틸기 등의 하이드록시 C1∼6 알킬기 ;
메톡시메틸기, 에톡시메틸기, 메톡시에틸기, 에톡시에틸기, 메톡시-n-프로필기, n-프로폭시메틸기, i-프로폭시에틸기, s-부톡시메틸기, t-부톡시에틸기 등의 C1∼6 알콕시 C1∼6 알킬기 ;
비닐옥시메틸기, 알릴옥시메틸기, 프로페닐옥시메틸기, 부테닐옥시메틸기 등의 C2∼6 알케닐옥시 C1∼6 알킬기 ;
피리딘-2-일옥시메틸기 등의 헤테로아릴옥시 C1∼6 알킬기 ;
포르밀기, 아세틸기, 프로피오닐기 등의 C1∼7 아실기 ;
포르밀옥시메틸기, 아세톡시메틸기, 2-아세톡시에틸기, 프로피오닐옥시메틸기, 프로피오닐옥시에틸기 등의 C1∼7 아실옥시 C1∼6 알킬기 ;
카르복실메틸기, 카르복실에틸기 등의 카르복실기 C1∼6 알킬기 ;
메톡시카르보닐메틸기, 에톡시카르보닐메틸기, n-프로폭시카르보닐메틸기, i-프로폭시카르보닐메틸기 등의 C1∼6 알콕시카르보닐 C1∼6 알킬기 ;
포름아미드메틸기, 아세트아미드메틸기, 2-아세트아미드에틸기, 프로피오닐아미노메틸기, 프로피오닐아미노에틸기 등의 C1∼7 아실아미노 C1∼6 알킬기 ;
메틸아미노카르보닐메틸기, 에틸아미노카르보닐메틸기, i-프로필아미노카르보닐메틸기, t-부틸아미노카르보닐메틸기, s-부틸아미노카르보닐메틸기, n-펜틸아미노카르보닐메틸기 등의 C1∼6 알킬아미노카르보닐 C1∼6 알킬기 ;
메톡시카르보닐아미노메틸기, 에톡시카르보닐아미노메틸기, i-프로폭시카르보닐아미노메틸기, t-부톡시카르보닐아미노메틸기, s-부틸옥시카르보닐아미노메틸기, n-펜틸옥시카르보닐아미노메틸기 등의 C1∼6 알콕시카르보닐아미노 C1∼6 알킬기 ;
벤질기, 페네틸기 등의 C7∼11 아르알킬기 ;
벤조일아미노메틸기 등의 C6∼10 아릴카르보닐아미노 C1∼6 알킬기 ;
등을 예시할 수 있다.
X 에 있어서의 「C3∼8 시클로알킬기」로는, 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기 등을 예시할 수 있다.
X 에 있어서의 「C2∼6 알케닐기」로는, 비닐기, 1-프로페닐기, 2-프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-메틸-2-프로페닐기, 2-메틸-2-프로페닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 4-펜테닐기, 1-메틸-2-부테닐기, 2-메틸-2-부테닐기, 1-헥세닐기, 2-헥세닐기, 3-헥세닐기, 4-헥세닐기, 5-헥세닐기 등을 예시할 수 있다.
「치환기를 갖는 C2∼6 알케닐기」로는, 2-클로로-1-프로페닐기, 2-플루오로-1-부테닐기 등의 C2∼6 할로알케닐기를 예시할 수 있다.
X 에 있어서의 「C2∼6 알키닐기」로는, 에티닐기, 1-프로피닐기, 2-프로피닐기, 1-부티닐기, 2-부티닐기, 3-부티닐기, 1-메틸-2-프로피닐기, 2-메틸-3-부티닐기, 1-펜티닐기, 2-펜티닐기, 3-펜티닐기, 4-펜티닐기, 1-메틸-2-부티닐기, 2-메틸-3-펜티닐기, 1-헥시닐기, 1,1-디메틸-2-부티닐기 등을 예시할 수 있다.
「치환기를 갖는 C2∼6 알키닐기」로는, 4,4-디클로로-1-부티닐기, 4-플루오로-1-펜티닐기, 5-브로모-2-펜티닐기 등의 C2∼6 할로알키닐기를 예시할 수 있다.
X 에 있어서의 「C1∼6 알콕시기」로는, 메톡시기, 에톡시기, n-프로폭시기, n-부톡시기, n-펜틸옥시기, n-헥실옥시기, i-프로폭시기, i-부톡시기, s-부톡시기, t-부톡시기, i-헥실옥시기 등을 예시할 수 있다.
「치환기를 갖는 C1∼6 알콕시기」로는, 클로로메톡시기, 디클로로메톡시기, 디플루오로메톡시기, 트리클로로메톡시기, 트리플루오로메톡시기, 1-플루오로에톡시기, 1,1-디플루오로에톡시기, 2,2,2-트리플루오로에톡시기, 펜타플루오로에톡시기 등의 C1∼6 할로알콕시기 등을 예시할 수 있다.
X 에 있어서의 「C1∼6 알킬아미노기」로는, 메틸아미노기, 디메틸아미노기, 디에틸아미노기 등을 예시할 수 있다.
X 에 있어서의 「C1∼7 아실기」로는, 포르밀기, 아세틸기, 프로피오닐기, 벤조일기 등을 예시할 수 있다.
「치환기를 갖는 C1∼7 아실기」로는, 클로로아세틸기, 트리플루오로아세틸기, 트리클로로아세틸기, 4-클로로벤조일기 등의 할로겐 치환 C1∼7 아실기를 예시할 수 있다.
X 에 있어서의 「C1∼6 알콕시카르보닐기」로는, 메톡시카르보닐기, 에톡시카르보닐기, n-프로폭시카르보닐기, i-프로폭시카르보닐기 등을 예시할 수 있다.
「치환기를 갖는 C1∼6 알콕시카르보닐기」로는,
시클로프로필메톡시카르보닐기, 시클로부틸메톡시카르보닐기, 시클로펜틸메톡시카르보닐기, 시클로헥실메톡시카르보닐기, 2-메틸시클로프로필메톡시카르보닐기, 2,3-디메틸시클로프로필메톡시카르보닐기, 2-클로로시클로프로필메톡시카르보닐기, 2-시클로프로필에톡시카르보닐기 등의 C3∼8 시클로알킬 C1∼6 알콕시카르보닐기 ;
플루오로메톡시카르보닐기, 클로로메톡시카르보닐기, 브로모메톡시카르보닐기, 디플루오로메톡시카르보닐기, 디클로로메톡시카르보닐기, 디브로모메톡시카르보닐기, 트리플루오로메톡시카르보닐기, 트리클로로메톡시카르보닐기, 트리브로모메톡시카르보닐기, 2,2,2-트리플루오로에톡시카르보닐기, 2,2,2-트리클로로에톡시카르보닐기, 펜타플루오로에톡시카르보닐기, 4-플루오로부톡시카르보닐기, 3,3,3-트리플루오로프로폭시카르보닐기, 2,2,2-트리플루오로-1-트리플루오로메틸에톡시카르보닐기, 퍼플로로헥실옥시카르보닐기 등의 C1∼6 할로알콕시카르보닐기 ;
등을 예시할 수 있다.
X 에 있어서의 「C1∼6 알킬술포닐기」로는, 메틸술포닐기, 에틸술포닐기, t-부틸술포닐기 등을 예시할 수 있다.
X 에 있어서의 「C1∼6 알콕시술포닐기」로는, 메톡시술포닐기, 에톡시술포닐기, t-부톡시술포닐기 등을 예시할 수 있다.
X 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」로는, 상기 Cy 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
X 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」 상의 치환기로는,
불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자 ;
메틸기, 에틸기, n-프로필기, i-프로필기, n-부틸기, s-부틸기, i-부틸기, t-부틸기, n-펜틸기, n-헥실기 등의 C1∼6 알킬기 ;
클로로메틸기, 클로로에틸기, 트리플루오로메틸기, 1,2-디클로로-n-프로필기, 1-플루오로-n-부틸기, 퍼플루오로-n-펜틸기 등의 C1∼6 할로알킬기 ;
시아노기 ;
등을 예시할 수 있다.
X 에 있어서의 「하이드록시이미노 C1∼6 알킬기」로는, 하이드록시이미노메틸기, (1-하이드록시이미노)에틸기, (1-하이드록시이미노)프로필기 등을 예시할 수 있다.
「치환기를 갖는 하이드록시이미노 C1∼6 알킬기」로는, 메톡시이미노메틸기, (1-메톡시이미노)에틸기, (1-메톡시이미노)프로필기, 에톡시이미노메틸기, (1-에톡시이미노)에틸기, (1-에톡시이미노)프로필기 등의 C1∼6 알콕시이미노 C1∼6 알킬기 ; (1-시클로프로필메톡시이미노)에틸기 등의 C3∼8 시클로알킬 C1∼6 알콕시이미노 C1∼6 알킬기 ; 벤질옥시이미노메틸기, (1-벤질옥시이미노)에틸기 등의 C7∼11 아르알킬옥시이미노 C1∼6 알킬기 등을 예시할 수 있다.
X 에 있어서의 「할로겐 원자」로는, 불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등을 예시할 수 있다.
n 이 2 이상일 때에, X 가 하나가 되어 결합하는 탄소 원자 또는 질소 원자와 함께 형성하는 고리로는, 시클로펜텐 고리, 시클로헥센 고리, 3,4-디하이드로-2H-피란 고리, 3,4-디하이드로-2H-티오피란 고리, 3,4-디하이드로-2H-티오피란 1,1-디옥사이드 고리 등을 예시할 수 있다.
[R1]
식 (I) 중, R1 은 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 또는 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기를 나타낸다.
R1 에 있어서의 「C1∼6 알킬기」, 「C2∼6 알케닐기」, 「C2∼6 알키닐기」, 「C1∼7 아실기」, 및 「C1∼6 알콕시카르보닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
[Q]
식 (I) 중, Q 는 식 (II), 식 (III), 또는 식 (IV) 로 나타내는 기를 나타낸다.
[화학식 12]
식 (II) 중, * 는 결합 위치를 나타낸다.
[R2]
식 (II) 중, R2 는 수소 원자, 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 또는 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기를 나타내고, R1 과 R2 는 하나가 되어 비치환의 혹은 치환기를 갖는 C2∼4 알킬렌기를 형성해도 된다.
R2 에 있어서의 「C1∼6 알킬기」, 「C2∼6 알케닐기」, 「C2∼6 알키닐기」, 「C1∼7 아실기」, 및 「C1∼6 알콕시카르보닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R1 과 R2 가 하나가 되어 형성하는 「비치환의 혹은 치환기를 갖는 C2∼4 알킬렌기」로는, 에틸렌기, 프로필렌기 (트리메틸렌기) 등을 예시할 수 있다.
[R3, R4]
식 (II) 중, R3 및 R4 는 각각 독립적으로 수소 원자, 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 또는 시아노기를 나타낸다. 여기서, R3 과 R4 는 하나가 되어 결합하는 탄소 원자와 함께 고리를 형성해도 된다.
R3 및 R4 에 있어서의 「C1∼6 알킬기」, 「C2∼6 알케닐기」, 및 「C2∼6 알키닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R3 및 R4 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」로는, 상기 Cy 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R3 과 R4 가 하나가 되어 결합하는 탄소 원자와 같이 형성하는 「고리」로는, 시클로프로판 고리, 시클로부탄 고리, 시클로펜탄 고리, 시클로헥산 고리, 옥시란 고리 등을 예시할 수 있다.
[R5]
식 (II) 중, R5 는 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C1∼7 아실기, 카르복실기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐옥시카르보닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐옥시카르보닐기, 비치환의 혹은 치환기를 갖는 아미노카르보닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 혹은 치환기를 갖는 하이드록시이미노 C1∼6 알킬기, 또는 시아노기를 나타낸다.
R5 에 있어서의, 「C1∼6 알킬기」, 「C3∼8 시클로알킬기」, 「C2∼6 알케닐기」, 「C2∼6 알키닐기」, 「C1∼7 아실기」, 및 「C1∼6 알콕시카르보닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R5 에 있어서의 「C6∼10 아릴기」로는, 페닐기, 나프틸기, 아줄레닐기, 인데닐기, 인다닐기, 테트랄리닐기 등을 예시할 수 있다.
R5 에 있어서의 「헤테로아릴기」로는, 피롤릴기, 푸릴기, 티에닐기, 이미다졸릴기, 피라졸릴기, 옥사졸릴기, 이소옥사졸릴기, 티아졸릴기, 이소티아졸릴기, 트리아졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 테트라졸릴기 등의 5 원자 고리의 헤테로아릴기 ;
피리딜기, 피라지닐기, 피리미디닐기, 피리다지닐기, 트리아지닐기 등의 6 원자 고리의 헤테로아릴기 ;
인돌릴기, 벤조푸릴기, 벤조티에닐기, 벤조이미다졸릴기, 벤조옥사졸릴기, 벤조티아졸릴기, 퀴놀릴기, 이소퀴놀릴기, 퀴녹살리닐기 등의 축합 고리의 헤테로아릴기 ;
피롤리닐기, 이미다졸리닐기, 피라졸리닐기, 옥사졸리닐기, 티아졸리닐기 등의 부분 불포화 5 원자 헤테로 고리 등을 예시할 수 있다.
바람직하게는, 페닐기, 피리딜기 등을 예시할 수 있다.
R5 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」 상의 치환기로는,
불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자 ;
메틸기, 에틸기, n-프로필기, i-프로필기, n-부틸기, s-부틸기, i-부틸기, t-부틸기, n-펜틸기, n-헥실기 등의 C1∼6 알킬기 ;
클로로메틸기, 클로로에틸기, 트리플루오로메틸기, 1,2-디클로로-n-프로필기, 1-플루오로-n-부틸기, 퍼플루오로-n-펜틸기 등의 C1∼6 할로알킬기 ;
시아노기 ;
등을 예시할 수 있다.
「C2∼6 알케닐옥시카르보닐기」로는, 에테닐옥시카르보닐기, 1-메틸-2-프로페닐옥시카르보닐기, 2-메틸-1-프로페닐옥시카르보닐기 등을 예시할 수 있다.
「C2∼6 알키닐옥시카르보닐기」로는, 에티닐옥시카르보닐기, 프로파르길옥시카르보닐기, 1-메틸프로파르길옥시카르보닐기, 2-부티닐옥시카르보닐기 등을 예시할 수 있다.
「치환기를 갖는 아미노카르보닐기」로는, 메틸아미노카르보닐기, 에틸아미노카르보닐기, i-프로필아미노카르보닐기, t-부틸아미노카르보닐기, s-부틸아미노카르보닐기, n-펜틸아미노카르보닐기 등의 C1∼6 알킬아미노카르보닐기 ; 디메틸아미노카르보닐기, 디에틸아미노카르보닐기 등의 디 C1∼6 알킬아미노카르보닐기 ; 시클로프로필아미노카르보닐기, 시클로펜틸아미노카르보닐기, 시클로헥실아미노카르보닐기 등의 C3∼8 시클로알킬아미노카르보닐기 ; 2-프로피닐아미노카르보닐기 등의 C2∼6 알키닐아미노카르보닐기 ; 페닐아미노카르보닐기, N-페닐-N-메틸아미노카르보닐기 ; 메톡시에틸아미노카르보닐기 등의 C1∼6 알콕시 C1∼6 알킬아미노카르보닐기 ; 2,2,2-트리플루오로에틸아미노카르보닐기 등의 C1∼6 할로알킬아미노카르보닐기 ; 시클로프로필메틸아미노카르보닐기 등의 C3∼8 시클로알킬 C1∼6 알킬아미노카르보닐기 ; 벤질아미노카르보닐기 등의 C7∼11 아르알킬아미노카르보닐기 ; 피페리딘-1-일카르보닐기 등의, 1 위치 치환-고리형 아민카르보닐기 등을 예시할 수 있다.
「하이드록시이미노 C1∼6 알킬기」로는, 하이드록시이미노메틸기, (1-하이드록시이미노)에틸기, (1-하이드록시이미노)프로필기 등을 예시할 수 있다.
「치환기를 갖는 하이드록시이미노 C1∼6 알킬기」로는, 메톡시이미노메틸기, (1-메톡시이미노)에틸기, (1-메톡시이미노)프로필기, 에톡시이미노메틸기, (1-에톡시이미노)에틸기, (1-에톡시이미노)프로필기 등의 C1∼6 알콕시이미노 C1∼6 알킬기 ; (1-시클로프로필메톡시이미노)에틸기 등의 C3∼8 시클로알킬 C1∼6 알콕시이미노 C1∼6 알킬기 ; 벤질옥시이미노메틸기, (1-벤질옥시이미노)에틸기 등의 C7∼11 아르알킬옥시이미노 C1∼6 알킬기 등을 예시할 수 있다.
[화학식 13]
식 (III) 중, * 는 결합 위치를 나타낸다.
[R6, R7]
식 (III) 중, R6 및 R7 은 각각 독립적으로 비치환의 혹은 치환기를 갖는 C1∼6 알킬기, 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C2∼6 알케닐기, 비치환의 혹은 치환기를 갖는 C2∼6 알키닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 또는 비치환의 혹은 치환기를 갖는 헤테로아릴기를 나타낸다. 여기서, R6 과 R7 은 하나가 되어 결합하는 황 원자와 함께 고리를 형성해도 된다.
R6 및 R7 에 있어서의 「C1∼6 알킬기」, 「C3∼8 시클로알킬기」, 「C2∼6 알케닐기」, 및 「C2∼6 알키닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R6 및 R7 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」로는, 상기 Cy 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R6 및 R7 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」 상의 치환기로는,
불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자 ;
메틸기, 에틸기, n-프로필기, i-프로필기, n-부틸기, s-부틸기, i-부틸기, t-부틸기, n-펜틸기, n-헥실기 등의 C1∼6 알킬기 ;
클로로메틸기, 클로로에틸기, 트리플루오로메틸기, 1,2-디클로로-n-프로필기, 1-플루오로-n-부틸기, 퍼플루오로-n-펜틸기 등의 C1∼6 할로알킬기 ;
시아노기 ;
등을 예시할 수 있다.
R6 과 R7 이 하나가 되어 결합하는 황 원자와 같이 형성하는 「고리」로는, 테트라하이드로티오펜 고리, 테트라하이드로티오피란 고리, 옥사티안 고리 등을 예시할 수 있다.
[화학식 14]
상기 식 (IV) 중, * 는 결합 위치를 나타낸다. R2 는 상기와 동일한 의미를 나타낸다. R8 은 비치환의 혹은 치환기를 갖는 C3∼8 시클로알킬기, 비치환의 혹은 치환기를 갖는 C1∼6 알콕시카르보닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 또는 비치환의 혹은 치환기를 갖는 헤테로아릴기를 나타낸다.
R8 에 있어서의 「C3∼8 시클로알킬기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
「치환기를 갖는 C3∼8 시클로알킬기」로는, 2-페닐시클로프로필기 등의, C6∼10 아릴 C3∼8 시클로알킬기 등을 예시할 수 있다.
R8 에 있어서의 「C1∼6 알콕시카르보닐기」로는, 상기 X 에 있어서 예시한 그들과 동일한 것을 들 수 있다.
R8 에 있어서의 「C6∼10 아릴기」로는, 페닐기, 나프틸기, 아줄레닐기, 인데닐기, 인다닐기, 테트랄리닐기 등을 예시할 수 있다.
R8 에 있어서의 「헤테로아릴기」로는, 피롤릴기, 푸릴기, 티에닐기, 이미다졸릴기, 피라졸릴기, 옥사졸릴기, 이소옥사졸릴기, 티아졸릴기, 이소티아졸릴기, 트리아졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 테트라졸릴기 등의 5 원자 고리의 헤테로아릴기 ;
피리딜기, 피라지닐기, 피리미디닐기, 피리다지닐기, 트리아지닐기 등의 6 원자 고리의 헤테로아릴기 ;
인돌릴기, 벤조푸릴기, 벤조티에닐기, 벤조이미다졸릴기, 벤조옥사졸릴기, 벤조티아졸릴기, 퀴놀릴기 등의 축합 고리의 헤테로아릴기 ;
테트라하이드로퀴놀릴기 등의 부분 포화 축합 헤테로 고리 ;
등을 예시할 수 있다.
R8 에 있어서의 「C6∼10 아릴기」 및 「헤테로아릴기」 상의 치환기로는,
불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자 ;
메틸기, 에틸기, n-프로필기, i-프로필기, n-부틸기, s-부틸기, i-부틸기, t-부틸기, n-펜틸기, n-헥실기 등의 C1∼6 알킬기 ;
클로로메틸기, 클로로에틸기, 트리플루오로메틸기, 1,2-디클로로-n-프로필기, 1-플루오로-n-부틸기, 퍼플루오로-n-펜틸기 등의 C1∼6 할로알킬기 ;
시아노기 ;
등을 예시할 수 있다.
[Z]
식 (I) 중, Z 는 산소 원자 또는 황 원자를 나타낸다. 바람직하게는 산소 원자이다.
[식 (V) 로 나타내는 아릴옥시우레아 화합물]
본 발명에 관련된 아릴옥시우레아 화합물 중, 식 (I) 중의 Cy 가 페닐기이며 또한 Q 가 식 (II) 으로 나타내는 기인 화합물이 바람직하다. 즉, 식 (V) 로 나타내는 아릴옥시우레아 화합물이 바람직하다.
[화학식 15]
상기 식 (V) 중, R1 ∼ R5, X, n, 및 Z 는 상기와 동일한 의미를 나타낸다.
[아릴옥시우레아 화합물의 염]
본 발명의 아릴옥시우레아 화합물의 염은 농원예학적으로 허용되는 염이면 특별히 제한되지 않는다. 예를 들어, 염산, 황산 등의 무기산의 염 ; 아세트산, 락트산 등의 유기산의 염 ; 리튬, 나트륨, 칼륨 등의 알칼리 금속의 염 ; 칼슘, 마그네슘 등의 알칼리 토금속의 염 ; 철, 구리 등의 천이 금속의 염 ; 암모니아, 트리에틸아민, 트리부틸아민, 피리딘, 히드라진 등의 유기 염기의 염 등을 들 수 있다. 아릴옥시우레아 화합물의 염은 공지된 수법에 의해서 얻을 수 있다.
[제조 방법]
다음으로, 본 발명의 아릴옥시우레아 화합물의 제조 방법에 관해서 설명한다.
1) 제 1 제조 방법으로서, 이하의 스킴에 나타내는 제조 방법을 예시할 수 있다.
[화학식 16]
a) 식 (1) 로 나타내는 아릴옥시아민 화합물 (이하, 「화합물 (1)」이라고 하는 경우가 있다) 에, 염기 존재하 클로로포름산페닐을 반응시켜, 식 (2) 로 나타내는 디에스테르 화합물 (이하, 「화합물 (2)」라고 하는 경우가 있다) 을 얻는다. 다음으로 이것을 트리플루오로아세트산 존재하에서 탈 Boc 화하여, 식 (3) 으로 나타내는 N-아릴옥시카르밤산페닐에스테르 화합물 (이하, 「화합물 (3)」이라고 하는 경우가 있다) 을 제조한다. 또, 식 (1) ∼ 식 (3) 중, X, n, 및 Cy 는 상기와 동일한 의미이다)
클로로포름산페닐의 사용량은 화합물 (1) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
이 반응은 염기의 비존재하에서 실시할 수도 있지만, 염기의 존재하에 실시하는 것이 바람직하다. 염기로는, 피리딘, 트리에틸아민, 수산화칼륨 등을 들 수 있다. 염기의 사용량은 화합물 (1) 1 몰에 대하여 통상 1 ∼ 2 몰이다.
이 반응은 용매 중에서 실시할 수 있다. 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 예를 들어, 디옥산, 1,2-디메톡시에탄, 테트라하이드로푸란 등의 에테르계 용매 ; 톨루엔, 벤젠, 자일렌 등의 방향족 탄화수소계 용매 ; n-펜탄, n-헥산, n-헵탄 등의 지방족 탄화수소계 용매 ; 디클로로메탄, 클로로포름, 사염화탄소, 1,2-디클로로에탄 등의 할로겐화 탄화수소계 용매 ; N,N-디메틸포름아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈 등의 아미드계 용매 ; 아세토니트릴, 벤조니트릴 등의 니트릴계 용매 ; 및 이들의 2 종 이상으로 이루어지는 혼합 용매 등을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (1) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 -20 ℃ 에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 ∼ 수 십 시간이다.
계속되는 탈 Boc 화 반응은 산촉매 존재하에서 실시한다. 사용하는 산으로는, 염산, 황산, 질산 등의 무기산 ; 아세트산, 트리플루오로아세트산, 메탄술폰산, p-톨루엔술폰산 등을 들 수 있는데, 트리플루오로아세트산이 바람직하다. 산의 사용량은 화합물 (2) 1 몰에 대하여 통상 1 ∼ 20 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (2) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 실온에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 내지 수 십 시간이다.
b) 화합물 (3) 에, 식 (4) 로 나타내는 화합물 (이하, 「화합물 (4)」라고 하는 경우가 있다) 를 반응시켜, 식 (5) 로 나타내는 아릴옥시우레아 화합물 (이하, 「화합물 (5)」라고 하는 경우가 있다) 을 제조한다. 여기서, 화합물 (4) 는 식 (4-1) 로 나타내는 아민 화합물 (이하, 「화합물 (4-1)」이라고 하는 경우가 있다), 식 (4-2) 로 나타내는 술폭시이민 화합물 (이하, 「화합물 (4-2)」라고 하는 경우가 있다), 또는 식 (4-3) 으로 나타내는 아민 화합물 (이하, 「화합물 (4-3)」이라고 하는 경우가 있다) 중 어느 하나이다 (식 (4) 및 식 (5) 중, X, n, Q, 및 Cy 는 상기와 동일한 의미이다. 식 (4-1), 식 (4-2), 및 식 (4-3) 중, R2 ∼ R8 은 상기와 동일한 의미이다).
화합물 (4) 의 사용량은 화합물 (3) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (3) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
또, 화합물 (4-2) 를 반응시키는 경우에는, 염기의 존재하에 실시하는 것이 바람직하다. 염기로는, 피리딘, 트리에틸아민, 수산화칼륨 등을 들 수 있다. 염기의 사용량은 화합물 (3) 1 몰에 대하여 통상 1 ∼ 2 몰이다.
반응 온도는 실온에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 ∼ 수 십 시간이다.
b) 화합물 (5) 에, 염기 존재하 식 (6) 으로 나타내는 요오드화물 (이하, 「화합물 (6)」이라고 하는 경우가 있다) 을 반응시켜, 목적물인 식 (7) 로 나타내는 아릴옥시우레아 화합물 (이하, 「화합물 (7)」이라고 하는 경우가 있다) 을 제조한다 (식 (6), 및 식 (7) 중, X, n, Q, R1, 및 Cy 는 상기와 동일한 의미이다).
화합물 (6) 의 사용량은 화합물 (5) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
염기로는, 피리딘, 트리에틸아민, 수산화칼륨, 탄산칼슘 등을 들 수 있다. 염기의 사용량은 화합물 (5) 1 몰에 대하여 통상 1 ∼ 2 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (5) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 -20 ℃ 에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 ∼ 수 십 시간이다.
2) 제 2 제조 방법으로서, 이하의 스킴에 나타내는 제조 방법을 예시할 수 있다.
[화학식 17]
a) 이미 알려진 방법으로 조제 가능한 N-벤질옥시카르밤산페닐에스테르 (이하, 「화합물 (8)」이라고 하는 경우가 있다) 에 화합물 (4) 를 반응시켜, 식 (9) 로 나타내는 벤질옥시우레아 화합물 (이하, 「화합물 (9)」라고 하는 경우가 있다) 을 제조한다 (식 (9) 중, Q 는 상기와 동일한 의미이다)
화합물 (4) 의 사용량은 화합물 (8) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (8) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
또, 화합물 (4-2) 를 반응시키는 경우에는, 염기의 존재하에 실시하는 것이 바람직하다. 염기로는, 피리딘, 트리에틸아민, 수산화칼륨 등을 들 수 있다. 염기의 사용량은 화합물 (8) 1 몰에 대하여 통상 1 ∼ 2 몰이다.
반응 온도는 실온에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 ∼ 수 십 시간이다.
b) 화합물 (9) 에 화합물 (6) 을 반응시켜, 식 (10) 으로 나타내는 벤질옥시우레아 화합물 (이하, 「화합물 (10)」이라고 하는 경우가 있다) 로 한 후, 접촉 환원에 의해 탈벤질화하여, 식 (11) 로 나타내는 옥시우레아 화합물 (이하, 「화합물 (11)」이라고 하는 경우가 있다) 을 제조한다 (식 (10) 및 식 (11) 중, Q 및 R1 은 상기와 동일한 의미이다).
화합물 (6) 의 사용량은 화합물 (9) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (9) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 -20 ℃ 에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 ∼ 수 십 시간이다.
계속되는 탈벤질화 반응은 팔라듐 촉매 등에 의한 접촉 수소 환원에 의해 실시한다. 사용하는 팔라듐 촉매로는, 팔라듐블랙, 팔라듐카본 등을 들 수 있다. 팔라듐 촉매의 사용량은 화합물 (10) 1 몰에 대하여 통상 0.01 ∼ 0.1 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 그 밖에도, 메탄올, 에탄올, n-프로판올 등의 알코올계 용매 등을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (10) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 실온에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 내지 수 십 시간이다.
c) 화합물 (11) 에, 염기 존재하 식 (12) 로 나타내는 아릴 화합물 (이하, 「화합물 (12)」라고 하는 경우가 있다) 를 반응시켜, 목적물인 화합물 (7) 을 제조한다 (식 (12) 중, X, n, 및 Cy 는 상기와 동일한 의미이고, X' 는 불소 원자 등을 나타낸다).
화합물 (12) 의 사용량은 화합물 (11) 1 몰에 대하여 통상 1 ∼ 2 몰, 바람직하게는 1.0 ∼ 1.2 몰이다.
염기로는, 수산화리튬, 수산화나트륨, 수산화칼륨, 수산화마그네슘, 수산화칼슘 등의 금속 수산화물 ; 나트륨메톡사이드, 나트륨에톡사이드, 칼륨메톡사이드, 칼륨에톡사이드, 칼륨t-부톡사이드 등의 금속 알콕사이드 ; 수소화나트륨, 수소화칼륨, 수소화칼슘 등의 금속 수소화물 ; 트리에틸아민, 디이소프로필에틸아민, 피리딘, 1,8-디아자비시클로[5.4.0]운데세-7-엔 (DBU), 1,4-디아자비시클로[2.2.2]옥탄 등의 유기 염기 등을 들 수 있다. 염기의 사용량은 화합물 (11) 1 몰에 대하여 통상 1 ∼ 2 몰이다.
이 반응은 용매 중에서 실시된다. 사용하는 용매는 반응에 불활성인 것이면 특별히 제한되지 않는다. 화합물 (2) 의 제조에 사용하는 것으로서 예시한 용매와 동일한 것을 들 수 있다. 용매의 사용량은 특별히 한정되지 않지만, 화합물 (11) 1 g 에 대하여 통상 1 ∼ 100 ㎖ 이다.
반응 온도는 -20 ℃ 에서부터 사용하는 용매의 비점까지의 온도 범위이다. 반응 시간은 반응 규모에 따라서도 다르지만, 통상 수 분간 내지 수 십 시간이다.
어느 반응에 있어서도, 반응 종료 후에는 통상적인 후처리 조작, 및 원하는 바에 따라서 증류, 재결정, 칼럼 크로마토그래피 등의 공지 관용의 정제 수단에 의해 정제하여 목적물을 단리할 수 있다.
목적물의 구조는 IR 스펙트럼, NMR 스펙트럼, 매스 스펙트럼, 원소 분석 등의 공지된 분석 수단에 의해 동정, 확인할 수 있다.
[유해 생물 방제제]
본 발명의 아릴옥시우레아 화합물 또는 그 염 (이하 「본 발명 화합물」이라고 하는 경우가 있다) 은 각종 해충 (진드기류를 포함한다) 또는 식물 병원균 등의 유해 생물의 방제에 유효하다. 특히 살진드기제 또는 살균제로서 유효하다.
[살진드기제]
다음으로, 본 발명 화합물을 유효 성분으로 하는 살진드기제에 관해서 설명한다. 본 발명 화합물은 살성충, 살약충 (殺若蟲), 살유충, 및 살란 (殺卵) 등의 작용을 갖는 점에서 농작물에 붙은 진드기류 등의 유해 생물의 방제에 사용할 수 있다. 특히 농작물, 과수, 화분, 수목에 붙은 진드기류에 대한 방제 효과가 우수하다.
방제의 대상이 되는 진드기류 (Acari) 의 예를 이하에 나타낸다.
(1) 무기문목 (Astigmata) 의 진응애류 (Acaridida) :
(a) 진응애과 (Acaridae) 의 진드기, 예를 들어 리조글리푸스속종 (Rhizoglyphus spp.) 의, 뿌리응애 (Rhizoglyphus echinopus), 로빈뿌리응애 (Rhizoglyphus robini) ; 긴털가루진드기속종 (Tyrophagus spp.) 의, 긴털가루진드기 (Tyrophagus putrescentiae), 온실긴털가루진드기 (Tyrophagus neiswanderi), 큰긴털가루진드기 (Tyrophagus perniciosus), 곤봉가루응애 (Tyrophagus similis) ; 기타, 가루진드기 (Acarus siro), 보리가루진드기 (Aleuroglyphus ovatus), 작은긴털가루진드기 (Mycetoglyphus fungivorus) ;
(2) 전기문목 (Prostigmata) 의 털진드기류 (Actinedida)
(a) 잎응애과 (Tetranychidae) 의 진드기, 예를 들어 브리오비아속종 (Bryobia spp.) 의, 클로버응애 (Bryobia praetiosa), 작은클로버응애 (Bryobia rubrioculus) ; 예를 들어 에오테트라니쿠스속종 (Eotetranychus spp.) 의, 살구응애 (Eotetranychus boreus), 제니쿨라투스응애 (Eotetranychus geniculatus), 밤응애 (Eotetranychus pruni), 호두응애 (Eotetranychus uncatus), 잣밤나무응애 (Eotetranychus shii), 뽕나무응애 (Eotetranychus suginamensis), 팽나무응애 (Eotetranychus celtis), 스미드응애 (Eotetranychus smithi), 코우노시로응애 (Eotetranychus asiaticus), 미야케응애 (Eotetranychus kankitus) ; 예를 들어 올리고니쿠스속종 (Oligonychus spp.) 의, 망고응애 (Oligonychus mangiferus), 아보가도응애 (Oligonychus perseae), 올리고니쿠스·푸스튤로수스 (Oligonychus pustulosus), 낙엽송잎응애 (Oligonychus karamatus), 삼나무응애 (Oligonychus hondoensis), 철쭉응애 (Oligonychus ilicis), 전나무잎응애 (Oligonychus ununguis), 벼응애 (Oligonychus shinkajii), 사탕수수응애 (Oligonychus orthius) ; 예를 들어 파노니쿠스속종 (Panonychus spp.) 의, 귤응애 (Panonychus citri), 뽕나무잎 (Panonychus mori), 사과응애 (Panonychus ulmi) ; 예를 들어 테트라니쿠스속종 (Tetranychus spp.) 의, 벚나무응애 (Tetranychus viennensis), 테트라니쿠스·퀘시보루스 (Tetranychus quercivorus), 테트라니쿠스·루데니 (Tetranychus ludeni), 테트라니쿠스·파셀루스 (Tetranychus phaselus), 붉은점박이응애 (Tetranychus cinnabarinus), 차응애 (Tetranychus kanzawai), 점박이응애 (Tetranychus urticae) ; 예를 들어 아포니쿠스속 (Aponychus spp.) 의, 넓은어깨응애 (Aponychus corpuzae), 벽오동응애 (Aponychus firmianae) ; 예를 들어 미도리응애속 (Sasanychus spp.) 의, 미도리응애 (Sasanychus akitanus), 히메미도리응애 (Sasanychus pusillus) ; 예를 들어 시조테트라니쿠스속 (Shizotetranychus spp.) 의, 납작대응애 (Shizotetranychus celarius), 시조테트라니쿠스·미스칸티 (Shizotetranychus miscanthi), 시조테트라니쿠스·론구스 (Shizotetranychus longus), 버드나무응애 (Shizotetranychus schizopus), 시조테트라니쿠스·렉키 (Shizotetranychus recki) ; 기타, 제주치레응애 (Tuckerella pavoniformis), 테트라니키나·하르티 (Tetranychina harti), 예조니쿠스·사포렌시스 (Yezonychus sapporensis) ;
(b) 애응애과 (Tenuipalpidae) 의 진드기, 예를 들어 브레비팔푸스속종 (Brevipalpus spp.) 의, 포도애응애 (Brevipalpus lewisi), 선인장애응애 (Brevipalpus russulus), 망초애응애 (Brevipalpus obovatus), 플랫마이트 (Brevipalpus phoenicis) ; 예를 들어 테니팔푸스속종 (Tenuipalpus spp.) 의, 양란애응애 (Tenuipalpus pacificus), 감나무애응애 (Tenuipalpus zhizhilashviliae) ; 기타, 파인애플애응애 (Dolichotetranychus floridanus) ;
(c) 흑응애과 (Eriophyidae) 의 진드기, 예를 들어 아세리아속종 (Aceria spp.) 의, 감녹진드기 (Aceria diospyri), 무화과녹진드기 (Aceria ficus), 밤흑응애 (Aceria japonica), 구기자흑응애 (Aceria kuko), 카네이션녹진드기 (Aceria paradianthi), 구기자흑응애 (Aceria tiyingi), 튤립녹진드기 (Aceria tulipae), 아세리아·조이시에아 (Aceria zoysiea) ; 예를 들어 에리오피에스속종 (Eriophyes spp.) 의, 작은배녹진드기 (Eriophyes chibaensis), 에리오피에스·에마르기나태 (Eriophyes emarginatae) ; 예를 들어 아쿠로프스속종 (Aculops spp.) 의, 토마토녹진드기 (Aculops lycopersici), 귤녹진드기 (Aculops pelekassi) ; 예를 들어 아쿠루스속종 (Aculus spp.) 의, 복숭아녹진드기 (Aculus fockeui), 사과녹진드기 (Aculus schlechtendali) ; 기타, 포도흑응애 (Colomerus vitis), 포도녹진드기 (Calepitrimerus vitis), 류큐귤녹진드기 (Phyllocotruta citri), 파라카라카루스·포도카프리 (Paracalacarus podocarpi), 차녹진드기 (Calacarus carinatus), 아카필라·테아바그란스 (Acaphylla theavagrans), 국화잎녹진드기 (Paraphytoptus kikus), 배녹진드기 (Epitrimerus pyri) ;
(d) 먼지응애과 (Transonemidae) 의 진드기, 예를 들어 타르소네무스속종 (Tarsonemus spp.) 의, 갈색먼지응애 (Tarsonemus bilobatus), 화백먼지응애 (Tarsonemus waitei) ; 기타, 시클라멘먼지응애 (Phytonemus pallidus), 차먼지응애 (Polyphagotarsonemus latus) ;
(e) 어스 마이트과 (Penthaleidae) 의 진드기, 예를 들어 펜탈레우스속종 (Penthaleus spp.) 의, 배추진드기 (Penthaleus erythrocephalus), 보리진드기 (Penthaleus major) ;
그리고, 동물에 기생하는 진드기류에 대한 방제 효과가 우수하다. 동물에 기생하는 진드기류는 숙주가 되는 동물 (숙주 동물) 의 등, 겨드랑이아래, 하복부, 허벅다리부 등에 기생하여 동물로부터 혈액이나 비듬 등의 영양원을 얻어 생식하는 것, 및 숙주 동물의 등, 둔부 등으로 날아와 동물로부터 혈액이나 비듬 등의 영양원을 얻어 생식하는 것을 포함한다. 대상이 되는 숙주 동물로는, 개, 고양이, 마우스, 래트, 햄스터, 몰모트, 다람쥐, 토끼, 족제비 ; 애완 조류 (예를 들어, 비둘기, 앵무새, 구관조, 문조, 잉꼬, 십자매, 카나리아) ; 소, 말, 돼지, 양, 염소 ; 가금 (예를 들어, 집오리, 닭, 메추리, 거위) ; 꿀벌 (예를 들어, 서양 꿀벌, 일본 꿀벌) 등을 들 수 있다.
방제의 대상이 되는 진드기류 (Acari) 의 예를 이하에 나타낸다.
(1) 중기문목 (Mesostigmata) 의 진드기류 (mite)
(a) 새진드기과 (Dermanyssidae) 의 진드기, 예를 들어 새진드기 (Dermanyssus gallinae) ;
(b) 가위집게진드기과 (Macronyssidae) 의 진드기, 예를 들어 집진드기속종 (Ornithonyssus spp.) 의, 오르니토니서스·실비아럼 (Ornithonyssus sylviarum), 오르니토니서스·부르사 (Ornithonyssus bursa), 집진드기 (Ornithonyssus bacoti) ;
(c) 가시응애과 (Laelapidae) 의 진드기, 예를 들어 가시응애속종 (Laelaps spp.) 의, 쥐좀진드기 (Laelaps echidninus), 비단털쥐좀진드기 (Laelaps jettmari) ; 꿀벌가시응애 (Tropilaelaps clarae)
(d) 꿀벌응애과 (Varroidae) 의 진드기, 예를 들어 꿀벌응애속종 (Varroa spp.) 의, 바로아·데스트룩토르 (Varroa destructor), 바로아·쟈콥소니 (Varroa jacobsoni), 바로아·언더우디 (Varroa underwoodi) ;
(2) 후기문목 (Metastigmata) 의 참진드기류 (tick)
(a) 공주진드기과 (Argasidae) 의 진드기, 예를 들어 아르가스속종 (Argas spp.) 의, 아르가스·퍼시쿠스 (Argas persicus), 아르가스·리플렉서스 (Argas reflexus) ; 예를 들어 공주진드기속종 (Ornithodoros spp.) 의, 오르니토도로스·모우바타 (Ornithodoros moubata) ;
(b) 참진드기과 (Ixodidae) 의 진드기, 예를 들어 가시들피참진드기속종 (Haemaphysalis spp.) 의, 헤마피살리스·콘시나 (Haemaphysalis concinna), 헤마피살리스·푼크타타 (Haemaphysalis punctata), 헤마피살리스·신아바리나 (Haemaphysalis cinnabarina), 헤마피살리스·오토필라 (Haemaphysalis otophila), 헤마피살리스·레아치 (Haemaphysalis leachi), 헤마피살리스·론기코르니스 (Haemaphysalis longicornis), 헤마피살리스·마게시마엔시스 (Haemaphysalis mageshimaensis), 헤마피살리스·예니 (Haemaphysalis yeni), 헤마피살리스·캄파눌라타 (Haemaphysalis campanulata), 헤마피살리스·펜타라기 (Haemaphysalis pentalagi), 헤마피살리스·프라바 (Haemaphysalis flava), 헤마피살리스·메가스피노사 (Haemaphysalis megaspinosa), 헤마피살리스·쟈포니카 (Haemaphysalis japonica), 헤마피살리스·도우글라시 (Haemaphysalis douglasi) ; 예를 들어 뭉뚝참진드기속종 (Amblyomma spp.) 의, 암블리오머·아메리카넘 (Amblyomma americanum), 암블리오머·바리에가툼 (Amblyomma variegatum), 암블리오머·마큐라툼 (Amblyomma maculatum), 암블리오머·헤브라에움 (Amblyomma hebraeum), 암블리오머·카졔넨스 (Amblyomma cajennense), 암블리오머·테스투디나리움 (Amblyomma testudinarium) ; 예를 들어 참진드기속종 (Ixodes spp.) 의, 익소디즈·리시누스 (Ixodes ricinus), 익소디즈·헥사고나스 (Ixodes hexagonus), 익소디즈·카니수가 (Ixodes canisuga), 익소디즈·피로서스 (Ixodes pilosus), 익소디즈·루비쿤더스 (Ixodes rubicundus), 익소디즈·스카푸라리스 (Ixodes scapularis), 익소디즈·호로시크루스 (Ixodes holocyclus), 익소디즈·오바투스 (Ixodes ovatus), 익소디즈·퍼술카투스 (Ixodes persulcatus), 익소디즈·닛포넨시스 (Ixodes nipponensis) ; 예를 들어 꼬리소진드기아속종 (Boophilus spp.) 의, 소진드기 (Rhipicephalus (Boophilus) microplus), 리피세팔러스 (부필러스)·데콜로라투스 (Rhipicephalus (Boophilus) decoloratus), 리피세팔러스 (부필러스)·아뉴라투스 (Rhipicephalus (Boophilus) annulatus), 리피세팔러스 (부필러스)·칼세라투스 (Rhipicephalus (Boophilus) calceratus) ; 예를 들어 개진드기속종 (Rhipicephalus spp.) 의, 리피세팔러스·에베르트시 (Rhipicephalus evertsi), 리피세팔러스·산귀네우스 (Rhipicephalus sanguineus), 리피세팔러스·부르사 (Rhipicephalus bursa), 리피세팔러스·아펜디쿨라투스 (Rhipicephalus appendiculatus), 리피세팔러스·카펜시스 (Rhipicephalus capensis), 리피세팔러스·투라니커스 (Rhipicephalus turanicus), 리피세팔러스·잠베지엔시스 (Rhipicephalus zambeziensis) ; 예를 들어 광대진드기속종 (Dermacentor spp.) 의, 더마센톨·마르기나투스 (Dermacentor marginatus), 더마센톨·레티쿨라투스 (Dermacentor reticulatus), 더마센톨·피크투스 (Dermacentor pictus), 더마센톨·알비피크투스 (Dermacentor albipictus), 더마센톨·안데르소니 (Dermacentor andersoni), 더마센톨·바리아빌리스 (Dermacentor variabilis) ;
(3) 무기문목 (Astigmata) 의 진응애류 (Acaridida)
(a) 귀진드기과 (Psoroptidae) 의 진드기, 예를 들어 귀진드기속종 (Psoroptes spp.) 의, 양귀진드기 (Psoroptes ovis), 토끼귀진드기 (Psoroptes cuniculi), 말귀진드기 (Psoroptes equi) ; 예를 들어 코리옵테스속종 (Chorioptes spp.) 의, 코리옵테스·보비스 (Chorioptes bovis) ; 옥토데크테스속종 (Otodectes spp.) 의, 옥토데크테스·시노티스 (Otodectes cynotis) ;
(b) 옴진드기과 (Sarcoptidae) 의 진드기, 예를 들어 옴진드기속종 (Sarcoptes spp.) 의, 사르코프테스·스카비에이 (Sarcoptes scabiei), 사르코프테스·카니스 (Sarcoptes canis), 사르코프테스·보비스 (Sarcoptes bovis), 사르코프테스·오비스 (Sarcoptes ovis), 사르코프테스·루피카프라에 (Sarcoptes rupicaprae), 사르코프테스·에쿠이 (Sarcoptes equi), 사르코프테스·수이스 (Sarcoptes suis) ; 예를 들어, 노토에드레스속종 (Notoedres spp.), 노토에드레스·카티 (Notoedres cati) ;
(c) 새옴진드기과 (Knemidokoptidae) 의 진드기, 예를 들어 새다리옴진드기속종 (Knemidokoptes spp.) 의 새다리옴진드기 (Knemidokoptes mutans) ;
(4) 전기문목 (Prostigmata) 의 털진드기류 (Actinedida)
(a) 모낭충진드기과 (Demodixidae) 의 진드기, 예를 들어 모낭충진드기속종 (Demodex spp.) 의, 개모낭충진드기 (Demodex canis), 소모낭충진드기 (Demodex bovis), 양모낭충진드기 (Demodex ovis), 염소모낭충진드기 (Demodex caprae), 말모낭충진드기 (Demodex equi), 데모덱스·카발리 (Demodex caballi), 돼지모낭충진드기 (Demodex suis), 고양이모낭충진드기 (Demodex cati) ;
(b) 쯔쯔가무시과 (Trombiculidae) 의 진드기, 예를 들어 쯔쯔가무시속종 (Trombicula spp.) 의, 트롬비큘라·알프레드게시 (Trombicula alfreddugesi), 트롬비큘라·아카무시 (Trombicula akamushi) ;
(c) 먼지응애와 (Tarsonemidae) 의 진드기, 예를 들어 아카라피스속종 (Acarapis spp.) 의, 옴응애 (Acarapis woodi) ;
[살충제]
또한, 본 발명 화합물은 농작물에 붙은 진드기류 이외의 해충, 위생 해충, 저각 해충, 의류 해충, 가옥 해충 등의 유해 생물의 방제에 사용할 수 있다.
방제의 대상이 되는 해충의 예를 이하에 나타낸다.
(1) 인시목 해충, 예를 들어, 담배거세미나방 (Spodoptera litura), 도둑나방 (Mamestra brassicae), 배추밤나방 (Agrotis ypsilon), 검은은무늬밤나방 (Autographa nigrisigna), 배추좀나방 (Plutella xylostella), 애모무늬잎말이나방 (Adoxophyes honmai), 차잎말이나방 (Homona magnanima), 복숭아심식나방 (Carposina sasakii), 심식나방 (Grapholitha molesta), 귤굴나방 (Phyllocnistis citrella), 동백가는나방 (Caloptilia theivora), 사과굴나방 (Phyllonorycter ringoniella), 매미나방 (Lymantria dispar), 차독나방 (Euproctis pseudoconspersa), 이화명나방 (Chilo suppressalis), 흑명나방 (Cnaphalocrocis medinalis), 유럽조명나방 (Ostrinia nubilalis), 미국흰불나방 (Hyphantria cunea), 줄알락명나방 (Cadra cautella), 헤리오티스속종 (Heliothis spp.), 헤리오베르파속종 (Helioverpa), 아그로티스속종 (Agrotis spp.), 옷좀나방 (Tinea translucens), 잎말이나방 (Cydia pomonella), 목화다래나방 (Pectinophora gossypiella) 등 ;
(2) 반시목 해충, 예를 들어, 복숭아혹진딧물 (Myzus persicae), 솜진딧물 (Aphis gossypii), 무우테두리진딧물 (Lipaphis erysimi), 기장테두리진딧물 (Rhopalosiphum padi), 톱다리허리노린재 (Riptortus clavatus), 풀노린재 (Acrosternum hilare), 화살깍지벌레 (Unaspis yanonensis), 뽕나무가루깍지벌레 (Pseudococcus comstocki), 온실가루이 (Trialeurodes vaporariorum), 담배가루이 (Bemisia tabaci), 꼬마배나무이 (Bemisia argentifolii), 배나무방패벌레 (Psylla pyricola), 배군배충 (Stephanitis nashi), 벼멸구 (Nilaparvata lugens), 애멸구 (Laodelphax stratella), 흰등멸구 (Sogatella furcifera), 끝동매미충 (Nephotettix cincticeps) 등 ;
(3) 갑충목 해충, 예를 들어, 벼룩잎벌레 (Phyllotreta striolata), 오이잎벌레 (Aulacophora indica), 콜로라도잎벌레 (Leptinotarsa decemlineata), 벼물바구미 (Lissorhoptrus oryzophilus), 바구미 (Sitophilus oryzae), 팥바구미 (Callosobruchus chinensis), 알풍뎅이 (Popillia japonica), 땅풍뎅이 (Anomala rufocuprea), 디아브로티카속종 (Diabrotica spp.), 권련벌레 (Lasioderma serricorne), 넓적나무좀 (Lyctus brunneus), 알락수염긴하늘소 (Monochamus alternatus), 알락하늘소 (Anoplophora malasiaca), 아그리오티스속 (Agriotes spp.), 이십팔점박이무당벌레 (Epilachna vigintioctomaculata), 느치 (Tenebroides mauritanicus), 목화바구미 (Anthonomus grandis) 등 ;
(4) 쌍시목 해충, 예를 들어, 오이과실파리 (Bactrocera cucurbitae), 귤코비파리 (Bactrocera dorsalis), 씨고자라니파리 (Delia platura), 벼잎물가파리 (Hydrellia griseola), 노랑초파리 (Drosophila melanogaster) 등 ;
(5) 총채벌레목 해충, 예를 들어, 오이총채벌레 (Thrips palmi), 볼록총채벌레 (Scirtothrips dorsalis) 등 ;
(6) 막시목 해충, 예를 들어, 애집개미 (Monomorium pharaonis), 노랑말벌 (Vespa simillima), 무우잎벌 (Athalia rosae) 등 ;
(7) 직시목 해충, 예를 들어, 풀무치 (Locusta migratoria) 등 ;
(8) 바퀴목 (Blattodea) 해충, 예를 들어, 독일바퀴 (Blattella germanica), 검은바퀴 (Periplaneta fuligginosa), 일본바퀴 (Periplaneta japonica), 이질바퀴 (Periplaneta americana), 잔이질바퀴 (Periplaneta australasiae) 등 ;
(9) 흰개미목 해충, 예를 들어, 집흰개미 (Coptotermes formosanus), 일본 흰개미 (Reticulitermes speratus) 등,
(10) 식물 기생성 선충류, 예를 들어, 고무마뿌리혹 선충 (Meloidogyne incognita), 뿌리썩이 선충류, 대두 시스토 선충 (Heterodera glycines), 벼잎 선충 (Aphelenchoides besseyi), 소나무재 선충 (Bursaphelenchus xylophilus) 등 ;
[외부 기생충 방제제]
그리고 본 발명 화합물은 동물에 기생하는 진드기류 이외의 외부 기생충에 대한 방제 효과가 우수하다.
방제제의 대상이 되는 이류 (Phthiraptera) 의 예를 이하에 나타낸다.
(1) 이아목 (Anoplura) 의 이류 (louse)
(a) 짐승이과 (Haematopinidae) 의 이, 예를 들어 돼지이속종 (Haematopinus spp.) 의, 말이 (Haematopinus asini), 소이 (Haematopinus eurysternus), 돼지이 (Haematopinus suis) ;
(b) 개이과 (Linognathidae) 의 이, 예를 들어 리노그나투스속종 (Linognathus spp.) 의, 개이 (Linognathus setosus), 소이 (Linognathus vituli), 리노그나투스·오빌러스 (Linognathus ovillus), 리노그나투스·오비포르미스 (Linognathus oviformis), 리노그나투스·페달리스 (Linognathus pedalis), 염소이 (Linognathus stenopsis) ; 예를 들어 솔레노포테스속종 (Solenopotes spp.) 의, 솔레노포테스·카필라투스 (Solenopotes capillatus) ;
(2) 새털이아목 (Amblycera) 의 새이류 (biting louse)
(a) 새털이과 (Menoponidae) 의 새이, 예를 들어 메나칸서스속종 (Menacanthus spp.) 의 메나칸서스·스트라미네우스 (Menacanthus stramineus), 메나칸서스·코르누투스 (Menacanthus cornutus), 메나칸서스·팔리두러스 (Menacanthus pallidulus) ; 예를 들어 메노폰속종 (Menopon spp.) 의, 메노폰·갈리나에 (Menopon gallinae) ;
(3) 세각아목 (Ischnocera) 의 새이류 (biting louse)
(a) 참새털이과 (Philopteridae) 의 새이, 예를 들어 콜롬비콜라속종 (Columbicola spp.) 의, 콜롬비콜라·콜롬바에 (Columbicola columbae) ; 예를 들어 쿠클로토가스터속종 (Cuclotogaster spp.) 의, 쿠클로토가스터·헤테로그라푸스 (Cuclotogaster heterographus) ; 예를 들어 고니오데스속종 (Goniodes spp.) 의, 고니오데스·디씨밀리스 (Goniodes dissimilis), 고니오데스·기가스 (Goniodes gigas), 고니오데스·갈리나에 (Goniodes gallinae) ; 예를 들어 리페우루스속종 (Lipeurus spp.) 의, 리페우루스·카포니스 (Lipeurus caponis) ;
(b) 짐승털이과 (Trichodectidae) 의 새이, 예를 들어 보비콜라속종 (Bovicola spp.) 의, 보비콜라·보비스 (Bovicola bovis), 보비콜라·오비스 (Bovicola ovis), 보비콜라·림바타 (Bovicola limbata), 보비콜라·카프라에 (Bovicola caprae), 보비콜라·에쿠이 (Bovicola equi) ; 예를 들어 짐승털이속종 (Trichodectes spp.) 의, 트리코데크테스·카니스 (Trichodectes canis) ; 예를 들어 페리콜라속종 (Felicola spp.) 의, 페리콜라·수브로스트라타 (Felicola subrostrata) ;
벼룩류 (Siphonaptera) 의 예를 이하에 나타낸다.
(a) 뚱뚱보벼룩과 (Tungidae) 의 벼룩, 예를 들어 뚱뚱보벼룩속종 (Tunga spp.) 의, 모래벼룩 (Tunga penetrans) ;
(b) 인간벼룩과 (Pulicidae) 의 벼룩, 예를 들어 개벼룩속종 (Ctenocephalides spp.) 의, 개벼룩 (Ctenocephalides canis), 고양이벼룩 (Ctenocephalides felis) ; 예를 들어 아르카에오씰라속종 (Archaeopsylla spp.) 의, 고슴도치벼룩 (Archaeopsylla erinacei) ; 예를 들어 쥐벼룩속종 (Xenopsylla spp.) 의, 동양쥐벼룩 (Xenopsylla cheopis) ; 예를 들어 인간벼룩속종 (Pulex spp.) 의, 인간벼룩 (Pulex irritans) ; 예를 들어 에키드노파가속종 (Echidnophaga spp.) 의, 닭벼룩 (Echidnophaga gallinacea) ;
(c) 쥐벼룩과 (Ceratophyllidae) 의 벼룩, 예를 들어 쥐벼룩속종 (Ceratophyllus spp.) 의, 닭벼룩 (Ceratophyllus gallinae), 일본 쥐벼룩 (Ceratophyllus anisus) ; 예를 들어 노소씰러스속종 (Nosopsyllus spp.) 의, 유럽쥐벼룩 (Nosopsyllus fasciatus),
(d) 장님쥐벼룩과 (Leptopsyllidae) 의 벼룩, 예를 들어 장님쥐벼룩속종 (Leptopsylla spp.) 의, 장님쥐벼룩 (Leptopsylla segnis) ;
그 밖에도, 대상이 되는 외부 기생충으로는 노린재목의 해충을 들 수 있다.
노린재목 (Hemiptera) 의 예를 이하에 나타낸다.
(a) 빈대과 (Cimicidae) 의 곤충, 예를 들어 시멕스속종 (Cimex spp.) 의, 빈대 (Cimex lectularius) ;
(b) 침노린재과 (Reduviidae) 의 곤충, 또한 트리아토마아과 (Triatominae) 의, 예를 들어 판스트론기러스속종 (Panstrongylus spp.) ; 예를 들어 로드니우스속종 (Rhodnius spp.) 의, 로드니우스·프로릭수스 (Rhodnius prolixus) ; 예를 들어 트리아토마속종 (Triatoma spp.) 의, 침노린재 (Triatoma infestans) ;
그 밖에도, 자교성 곤충 (저작성 파리, 흡혈 성충 파리, 이동성 쌍시류의 유충, 기생 파리의 구더기) 인 파리목 (Diptera) 해충에도 유효하다.
파리류 (Diptera) 의 예를 이하에 나타낸다.
(1) 장각아목 (Nematocera)
(a) 모기과 (Culicidae) 의 모기, 예를 들어 짐모기속종 (Culex spp.) 의, 열대집모기 (Culex quinquefasciatus), 큐렉스·피피엔스·팔렌스 (Culex pipiens pallens), 큐렉스·타르살리스 (Culex tarsalis), 큐렉스·피피엔스·모레스투스 (Culex pipiens molestus), 큐렉스·피피엔스·파티간스 (Culex pipiens fatigans), 큐렉스·트리타에니오린쿠스·숨모로서스 (Culex tritaeniorhynchus summorosus) ; 예를 들어 아르미게레스속종 (Armigeres spp.) 의, 아르미게레스·수발바투스 (Armigeres subalbatus) ; 예를 들어 아노페레스속종 (Anopheles spp.) 의 아노페레스·감비아에 (Anopheles gambiae), 아노페레스·마큐리페니스 (Anopheles maculipennis), 아노페레스·시넨시스 (Anopheles sinensis), 아노페레스·레스테리 (Anopheles lesteri) ; 예를 들어 에데스속종 (Aedes spp.) 의, 에데스·아에집티 (Aedes aegypti), 에데스·알보피크투스 (Aedes albopictus), 에데스·타에니오린쿠스 (Aedes taeniorhynchus), 에데스·토고이 (Aedes togoi), 에데스·베상스·닛포니 (Aedes vexans nipponii) ;
(b) 먹파리과 (Simuliidae) 의 먹파리, 예를 들어 먹파리속종 (Simulium spp.) 의, 시뮬리움·렙탄스 (Simulium reptans), 시뮬리움·오르나툼 (Simulium ornatum), 시뮬리움·베누스툼 (Simulium venustum), 시뮬리움·살로피엔세 (Simulium salopiense) ; 예를 들어 프로시뮬리움속종 (Prosimulium spp) 의, 프로시뮬리움·옌조엔세 (Prosimulium yezoense) ;
(c) 둥에모기과 (Ceratopogonidae) 의 둥에모기, 예를 들어 쿨리오데스속종 (Culiodes spp.) 의, 쿨리오데스·아라카와에 (Culicoides arakawae), 쿨리오데스·피크티마르고 (Culicoides pictimargo), 쿨리오데스·키부넨시스 (Culicoides kibunensis), 쿨리오데스·호모토무스 (Culicoides homotomus), 쿨리오데스·옥시스토마 (Culicoides oxystoma), 쿨리오데스·닛포넨시스 (Culicoides nipponensis), 쿨리오데스·푼크타투스 (Culicoides punctatus), 쿨리오데스·머큘라투스 (Culicoides maculatus), 쿨리오데스·마츠자와이 (Culicoides matsuzawai)
(2) 단각아목
(a) 등에과 (Tabanidae) 의 등에, 예를 들어 등에속종 (Tabanus spp.) 의, 타바누스·브로미우스 (Tabanus bromius), 타바누스·스포도프테루스 (Tabanus spodopterus), 타바누스·아트라투스 (Tabanus atratus), 타바누스·수데티쿠스 (Tabanus sudeticus), 타바누스·트리고누스 (Tabanus trigonus), 타바누스·크리수루스 (Tabanus chrysurus), 타바누스·트리게미누스 (Tabanus trigeminus), 타바누스·풀비메디오이데스 (Tabanus fulvimedioides), 타바누스·이요엔시스 (Tabanus iyoensis) ; 예를 들어 크리소프스속종 (Chrysops spp.) 의, 크리소프스·카에큐티엔스 (Chrysops caecutiens), 크리소프스·렐릭투스 (Chrysops relictus), 크리소프스·수아비스 (Chrysops suavis), 크리소프스·쟈포니쿠스 (Chrysops japonicus) ;
(e) 집파리과 (Muscidae) 의 파리, 예를 들어 집파리속종 (Muscina spp.) 의, 집파리 (Musca domestica), 무스카·베지이 (Musca bezzii), 무스카·헤르베이 (Musca hervei), 무스카·콘두센스 (Musca conducens), 무스카·스타부란스 (Musca stabulans), ; 예를 들어 침파리속종 (Stomoxys spp.) 의, 침파리 (Stomoxys calcitrans), ; 예를 들어 털침파리속종 (Haematobia spp.) 의, 헤마토비아·일리탄스 (Haematobia irritans), 헤마토비아·일리탄스·엑시구아 (Haematobia irritans exigua), 헤마토비아·스티뮤란스 (Haematobia stimulans) ; 아기집파리속종 (Fannia spp.) 의, 아기집파리 (Fannia canisularis) ;
(c) 체체파리과 (Glossinidae) 의 체체파리속종 (Glossina spp.) ;
(e) 이파리과 (Hippoboscidae) 의 파리, 예를 들어 멜로파거스속종 (Melophagus spp.) 의, 이파리 (Melophagus ovinus) ;
(e) 검정파리과 (Calliphoridae) 의 파리, 예를 들어 검정파리속종 (Calliphora) 의, 큰검정파리 (Calliphora lata) ; 예를 들어 금파리속종 (Lucilia spp.) 의, 루실리아·파에니시아·쿠프리나 (Lucilia (Phaenicia) cuprina), 루실리아·파에니시아·세리카타 (Lucilia (Phaenicia) sericata), 루실리아·일루스트리스 (Lucilia illustris) ; 예를 들어 크리소미이아속 (Chrysomyia. spp.) 의, 크리소미아·호미니보락스 (Chrysomya hominivorax), 크리소미아·클로로피가 (Chrysomya chloropyga), 크리소미아·베지아나 (Chrysomya bezziana) ;
(f) 말파리과 (Oestridae) 의 파리, 예를 들어 쇠파리아과 (Cuterebrinae) 의 쿠터레브라속종 (Cuterebra spp.) ; 예를 들어 소파리아과 (Hypodermatinae) 의, 또한 말파리속종 (Hypoderma spp.) 의, 말파리 (Hypoderma bovis), 히포데르마·리네아툼 (Hypoderma lineatum) ; 예를 들어 말파리아과 (Gasterophilinae) 의, 또한 말파리속종 (Gasterophilus spp.) 의, 말파리 (Gasterophilus intestinalis), 가스테로필러스·헤모로이달리스 (Gasterophilus haemorroidalis), 가스테로필러스·이네르미스 (Gasterophilus inermis), 가스테로필러스·나살리스 (Gasterophilus nasalis), 가스테로필러스·니그리코르니스 (Gasterophilus nigricornis), 가스테로필러스·페코럼 (Gasterophilus pecorum) ; 예를 들어 양파리아과 (Oestrinae) 의, 또한 양파리속종 (Oestrus spp.) 의, 양파리 (Oestrus ovis) ;
[살균제]
다음으로, 본 발명 화합물을 유효 성분으로 하는 살균제에 관해서 설명한다. 본 발명 화합물은 우수한 살균 작용을 갖는다는 점에서, 광범위한 종류의 사상균, 예를 들어 난균류 (Oomycetes), 자낭균류 (Ascomycetes), 불완전 균류 (Deuteromycetes), 담자균류 (Basidiomycetes) 에 속하는 균에서 유래하는 식물 병해의 방제에 사용할 수 있다.
방제의 대상이 되는 식물 병해의 예를 이하에 나타낸다.
「사탕무」 : 갈반병 (Cercospora beticola), 흑근병 (Aphanomyces cochlloides), 근부병 (Thanatephorus cucumeris), 엽부병 (Thanatephorus cucumeris) 등
「땅콩」 : 갈반병 (Mycosphaerella arachidis), 흑삽병 (Mycosphaerella berkeleyi) 등
「오이」 : 흰가루병 (Sphaerotheca fuliginea), 노균병 (Pseudoperonospora cubensis), 덩굴마름병 (Mycosphaerella melonis), 덩굴쪼김병 (Fusarium oxysporum), 균핵병 (Sclerotinia sclerotiorum), 회색 곰팡이병 (Botrytis cinerea), 탄저병 (Colletotrichum orbiculare), 검은별무늬병 (Cladosporium cucumerinum), 갈반병 (Corynespora cassicola), 묘마름병 (Pythium debaryanam, Rhizoctonia solani Kuhn), 반점세균병 (Pseudomonas syringae pv.Lecrymans) 등
「토마토」 : 회색 곰팡이병 (Botrytis cinerea), 잎곰팡이병 (Cladosporium fulvum), 역병 (Phytophthora infestans) 등
「가지」 : 회색 곰팡이병 (Botrytis cinerea), 검은마름병 (Corynespora melongenae), 흰가루병 (Erysiphe cichoracearum), 가지잎곰팡이병 (Mycovellosiella nattrassii) 등
「딸기」 : 회색 곰팡이병 (Botrytis cinerea), 흰가루병 (Sohaerotheca humuli), 탄저병 (Colletotrichum acutatum, Colletotrichum fragariae), 역병 (Phytophthora cactorum) 등
「양파」 : 회색 부패병 (Botrytis allii), 회색 곰팡이병 (Botrytis cinerea), 백반엽 마름병 (Botrytis squamosa), 노균병 (Peronospora destructor)
「양배추」 : 뿌리혹병 (Plasmodiophora brassicae), 연부병 (Erwinia carotovora), 노균병 (Peronospora parasitica) 등
「강낭콩」 : 균핵병 (Sclerotinia sclerotiorum), 회색 곰팡이병 (Botrytis cinerea) 등
「사과」 : 흰가루병 (Podosphaera leucotricha), 검은별무늬병 (Venturia inaequalis), 모니리아병 (Monilinia mali), 검은점병 (Mycosphaerella pomi), 부란병 (Valsa mali), 반점낙엽병 (Alternaria mali), 붉은별무늬병 (Gymnosporangium yamadae), 윤문병 (Botryosphaeria berengeriana), 탄저병 (Glomerella cingulata, Colletotrichum acutatum), 갈반병 (Diplocarpon mali), 그을음점병 (Zygophiala jamaicensis), 그을음반점병 (Gloeodes pomigena) 등
「감」 : 흰가루병 (Phyllactinia kakicola), 탄저병 (Gloeosporium kaki), 모무늬낙엽병 (Cercospora kaki) 등
「복숭아」 : 잿빛무늬병 (Monilinia fructicola), 검은별무늬병 (Cladosporium carpophilum), 호모프시스 부패병 (Phomopsis sp.) 등
「버찌」 : 잿빛무늬병 (Monilinia fructicola) 등
「포도」 : 회색 곰팡이병 (Botrytis cinerea), 흰가루병 (Uncinula necator), 만부병 (Glomerella cingulata, Colletotrichum acutatum), 노균병 (Plasmopara viticola), 새눈무늬병 (Elsinoe ampelina), 갈색점무늬병 (Pseudocercospora vitis), 흑부병 (Guignardia bidwellii) 등
「배」 : 검은별무늬병 (Venturia nashicola), 붉은별무늬병 (Gymnosporangium asiaticum), 흑반병 (Alternaria kikuchiana), 윤문병 (Botryosphaeria berengeriana), 흰가루병 (Phyllactinia mali) 등
「차」 : 윤문병 (Pestalotia theae), 탄저병 (Colletotrichum theae-sinensis) 등
「감귤」 : 창가병 (Elsinoe fawcetti), 푸른 곰팡이병 (Penicillium italicum), 초록 곰팡이병 (Penicillium digitatum), 회색 곰팡이병 (Botrytis cinerea), 흑점병 (Diaporthe citri), 궤양병 (Xanthomonas campestris pv.Citri) 등
「밀」 : 흰가루병 (Erysiphe graminis f.sp.tritici), 붉은 곰팡이병 (Gibberella zeae), 붉은녹병 (Puccinia recondita), 갈색 설부병 (Pythium iwayamai), 홍색 설부병 (Monographella nivalis), 눈무늬병 (Pseudocercosporella herpotrichoides), 잎마름병 (Septoria tritici), 부고병 (Leptosphaeria nodorum), 설부소립균핵병 (Typhula incarnata), 설부대립균핵병 (Myriosclerotinia borealis), 입고병 (Gaeumanomyces graminis) 등
「보리」 : 반엽 (斑葉) 병 (Pyrenophora graminea), 구름무늬병 (Rhynchosporium secalis), 겉깜부기병 (Ustilago tritici, U.nuda) 등
「벼」 : 도열병 (Pyricularia oryzae), 문고병 (Rhizoctonia solani), 키다리병 (Gibberella fujikuroi), 깨씨무늬병 (Cochliobolus miyabeanus), 묘입고병 (Pythium graminicolum), 백엽고병 (Xanthomonas oryzae), 벼입고 세균병 (Burkholderia plantarii), 갈조병 (Acidovorax avenae), 벼알마름 세균병 (Burkholderia glumae)
「담배」 : 균핵병 (Sclerotinia sclerotiorum), 흰가루병 (Erysiphe cichoracearum) 등
「튤립」 : 회색 곰팡이병 (Botrytis cinerea) 등
「벤트그래스」 : 설부대립균핵병 (Sclerotinia borealis), 적소병 (Pythium aphanidermatum) 등
「오처드그래스」 : 흰가루병 (Erysiphe graminis) 등
「대두」 : 자반병 (Cercospora kikuchii), 노균병 (Peronospora Manshurica), 줄기 역병 (Phytophthora sojae) 등
「감자」 : 역병 (Phytophthora infestans) 등
본 발명 화합물은 약해가 적고, 어류나 온혈 동물에 대한 독성이 낮아, 특별히 안전성이 높은 화합물이다.
본 발명의 유해 생물 방제제는 본 발명 화합물에서 선택되는 적어도 1 종을 유효 성분으로서 함유하는 것이다.
또한, 본 발명의 유해 생물 방제제는 본 발명 화합물만을 함유하는 것이어도 되지만, 고체 담체, 액체 담체, 가스상 담체 등의 담체를 함유하고 있어도 된다. 또, 본 발명의 유해 생물 방제제는 본 발명 화합물을 다공 세라믹판이나 부직포 등의 기재에 함침시킨 것이어도 된다. 그리고, 필요에 따라서 계면 활성제, 그 밖의 보조제를 첨가한 것이어도 된다.
본 발명의 유해 생물 방제제는 일반적인 농약이 취할 수 있는 형태, 즉 수화제, 입제, 분제, 유제, 수용제, 현탁제, 과립 수화제, 플로어블, 마이크로캡슐, 에어졸, 연무제, 가열증산제, 훈연제, 살진드기제의 경우에는 베이트제 등의 형태로 제제화할 수 있다.
고체 제형으로의 제제화에 있어서 사용되는 첨가제 및 담체로는, 대두분, 소맥분 등의 식물성 분말, 규조토, 인회석, 석고, 탤크, 벤토나이트, 파이로필라이트, 클레이 등의 광물성 미분말, 벤조산소다, 우레아, 망초 등의 유기 및 무기 화합물 등을 들 수 있다.
액체 제형으로의 제제화에 있어서 사용되는 용제로는, 케로신, 자일렌 및 석유계의 방향족 탄화수소, 시클로헥산, 시클로헥사논, 디메틸포름아미드, 디메틸술폭사이드, 알코올, 아세톤, 트리클로로에틸렌, 메틸이소부틸케톤, 광물유, 식물유, 물 등을 들 수 있다.
분사제로 제제화할 때에 사용되는 가스상 담체로는, 부탄 가스, LPG, 디메틸에테르, 탄산 가스 등을 들 수 있다.
독이 (毒餌) 의 기재로는, 곡물가루, 식물유, 당, 결정 셀룰로오스 등의 미끼 성분, 디부틸하이드록시톨루엔, 노르디하이드로구아이아레트산 등의 산화 방지제, 데하이드로아세트산 등의 보존료, 고추가루 등의 아이나 애완동물에 의한 오식 (誤食) 방지제, 치즈 향료, 양파 향료 등의 해충 유인성 향료 등을 들 수 있다.
제제화에 있어 균일하고 또한 안정적인 형태를 취하기 위해, 필요에 따라 계면 활성제를 첨가할 수 있다. 첨가할 수 있는 계면 활성제는 특별히 제한되지 않는다. 예를 들어, 폴리옥시에틸렌이 부가된 알킬페닐에테르, 폴리옥시에틸렌이 부가된 알킬에테르, 폴리옥시에틸렌이 부가된 고급 지방산 에스테르, 폴리옥시에틸렌이 부가된 소르비탄 고급 지방산 에스테르, 폴리옥시에틸렌이 부가된 트리스티릴페닐에테르 등의 비이온성 계면 활성제, 폴리옥시에틸렌이 부가된 알킬페닐에테르의 황산에스테르염, 알킬벤젠술폰산염, 고급 알코올의 황산에스테르염, 알킬나프탈렌술폰산염, 폴리카르복실산염, 리그닌술폰산염, 알킬나프탈렌술폰산염의 포름알데히드 축합물, 이소부틸렌-무수 말레산 공중합체 등을 들 수 있다.
제제 중에 있어서의 본 발명 화합물의 함유량은 통상 제제 전체에 대하여 바람직하게는 0.01 ∼ 90 중량%, 보다 바람직하게는 0.05 ∼ 85 중량% 이다.
이렇게 해서 얻어진 수화제, 유제, 플로어블제, 수용제, 과립 수화제는 물로 소정의 농도로 희석하여 용해액, 현탁액 또는 유탁액으로 하여, 또 분말제·입제는 그대로 식물 또는 토양에 살포할 수 있다.
또한, 방역용 살진드기제로서 사용하는 경우에는, 유제, 에어졸, 연무제, 독이, 진드기 방지 시트 등의 형태로 공급된 제제를 그대로 사용할 수 있다.
또, 본 발명의 유해 생물 방제제를, 소, 돼지 등의 가축류, 개, 고양이 등의 애완동물류의 동물에 기생하는 진드기류의 방제용 살진드기제로 하는 경우에는, 숙주 동물 1 ㎏ 에 대하여, 본 발명 화합물이 0.01 ∼ 1000 ㎎ 의 비율이 되는 양으로 사용할 수 있다.
방제용 살진드기제는 공지된 수의학적 수법으로 시용 (施用) 할 수 있다. 그 방법으로서, 예를 들어, 전신적 억제 (systemic control) 를 목적으로 하는 경우에는, 정제, 캡슐, 침지액, 사료 혼입, 좌약, 주사 (근육내, 피하, 정맥내, 복강내 등) 등에 의해 동물에 투여하는 방법 등을 들 수 있고, 비전신적 억제 (non-systemic control) 를 목적으로 하는 경우에는, 유성 또는 수성 액제를 분무, 끼얹기 (pour-on), 적하 (spot-on) 등에 의해 투여하는 방법, 수지에 살진드기제를 반죽해 넣고, 그 반죽물을 목걸이, 귀표 등의 적당한 형상으로 성형하여, 그것을 동물에 장착시키는 방법 등을 들 수 있다.
본 발명의 유해 생물 방제제는 살균제, 다른 살충·살진드기제, 살선충제, 살토양 해충제, 식물 조절제, 공력제, 비료, 토양 개량제, 동물용 사료 등과 혼용 또는 병용해도 된다.
본 발명의 유해 생물 방제제와 혼합하여 사용할 수 있는 살균제, 다른 살충·살진드기제, 살선충제, 살토양 해충제, 식물 성장 조절제의 대표예를 이하에 나타낸다.
살충·살진드기제, 살선충제, 살토양 해충제 :
(1) 유기 (티오)포스페이트계 : 아세페이트, 아자메티포스, 아진포스·메틸, 아진포스·에틸, 브로모포스·에틸, 브롬펜비포스, BRP, 클로르피리포스, 클로르피리포스·메틸, 클로르피리포스·에틸, 클로르펜빈포스, 카두사포스, 카르보페노티온, 클로르에톡시포스, 클로르메포스, 쿠마포스, 시아노펜포스, 시아노포스, CYAP, 다이아지논, 디크로보스, 디크로토포스, 디메토에이트, 디술포톤, 디메톤-S-메틸, 디메틸빈포스, 디메톤-S-메틸술폰, 디알리포스, 디크로펜티온, 디옥사벤조포스, 에티온, 에토프로포스, 에트림포스, EPN, 페나미포스, 페니트로티온, 펜티온, 펜술포티온, 플루피라조포스, 포노포스, 포르모티온, 포스메틸란, 헵테노포스, 이사조포스, 요오드펜포스, 이소펜포스, 이소옥사티온, 이프로벤포스, 말라티온, 메빈포스, 메타미드포스, 메티다티온, 모노크로토포스, 메카르밤, 메타크리포스, 날레드, 오메토에이트, 옥시디메톤·메틸, 파라옥손, 파라티온, 파라티온·메틸, 펜토에이트, 포살론, 포스메트, 포스파미돈, 포레이트, 폭심, 피리미포스·메틸, 피리미포스·에틸, 프로페노포스, 프로티오포스, 포스티아제이트, 포스포카르브, 프로파포스, 프로페탐포스, 프로토에이트, 피리다펜티온, 피라클로포스, 퀴날포스, 살리티온, 술프로포스, 술포텝, 테트라클로르빈포스, 테르부포스, 트리아조포스, 트리클로르폰, 테부피림포스, 테메포스, 티오메톤, 바미드티온 ;
(2) 카르바메이트계 : 알라니카르브, 알디카르브, 벤디오카르브, 벤푸라카르브, 카르바릴, 카르보푸란, 카르보술판, 페녹시카르브, 페노티오카르브, 메티오카르브, 메토밀, 옥사밀, 피리미카르브, 프로폭수르, 티오디카르, 트리아자메이트, 에티오펜카르브, 페노부카르브, MIPC, MPMC, MTMC, 피리다펜티온, 프라티오카르브, XMC, 알독시카르브, 알릭시카르브, 아미노카르브, 부펜카르브, 부타카르브, 부토카르복심, 부톡시카르복심, 클로에토카르브, 디메틸란, 포르메타네이트, 이소프로카르브, 메탐·나트륨, 메톨카르브, 프로메카르브, 티오파녹스, 트리메타카르브, 자일릴카르브 ;
(3) 피레트로이드계 : 알레트린, 비펜트린, 시플루트린, 베타·시플루트린, 시할로트린, 람다·시할로트린, 시페노트린, 시퍼메트린, 알파·시퍼메트린, 베타·시퍼메트린, 제타·시퍼메트린, 델타메트린, 에스펜발레레이트, 에토펜프록스, 펜프로파트린, 펜발레레이트, 이미프로트린, 퍼메트린, 프랄레트린, 피레트린, 피레트린 I, 피레트린 II, 레스메트린, 실라플루오펜, 플루발리네이트, 테플루트린, 테트라메트린, 트랄로메트린, 트랜스플루트린, 프로플루트린, 디메플루트린, 아크리나트린, 시클로프로트린, 할펜프록스, 플루시트리네이트, 비오알레트린, 비오에타노메트린, 비오퍼메트린, 비오레스메트린, 트랜스퍼메트린, 엠펜트린, 펜플루트린, 플루프로시트리네이트, 플루펜프록스, 플루메트린, 메토플루트린, 페노트린, 프로트리펜부트, 피레스메트린, 테랄레트린 ;
(4) 성장 조절 물질 :
(a) 키틴 합성 저해제 : 클로르플루아주론, 디플루벤주론, 플루시클록수론, 플루페녹수론, 헥사플루무론, 루페누론, 노발루론, 테플루벤주론, 트리플루무론, 비스트리플루론, 노비플루무론, 부프로페진, 헥시티아족스, 에톡사졸, 클로펜테진, 플루아주론, 펜플루론 ;
(b) 엑디손 앤타고니스트 : 할로페노지드, 메톡시페노지드, 테부페노지드, 크로마페노지드, 아자디락틴 ;
(c) 유약 호르몬양 (樣) 물질 (juvenile hormone analogue) : 피리프록시펜, 메토프렌, 디오페놀란, 에포페노난, 하이드로프렌, 키노프렌, 트리프렌 ;
(d) 지질 생합성 저해제 : 스피로디클로펜, 스피로메시펜, 스피로테트라메이트, 플로니카미드 ;
(5) 니코틴 수용체 애고니스트/앤타고니스트 화합물 : 아세타미프리드, 클로티아니딘, 디노테푸란, 이미다클로프리드, 니텐피람, 티아클로프리드, 티아메톡삼, 니티아진, 니코틴, 벤술탑, 카탑 ;
(6) GABA 앤타고니스트 화합물 :
(a) 아세토프롤, 에티프롤, 피프로닐, 바닐리프롤, 피라플루프롤, 피리프롤 ;
(b) 유기 염소계 ; 캄페크롤, 클로르단, 엔도술판, HCH, γ-HCH, 헵타크롤, 메톡시크롤
(7) 큰고리형 락톤 살충제 : 아바멕틴, 에마멕틴벤조산, 밀베멕틴, 레피멕틴, 스피노사드, 이벨멕틴, 세라멕틴, 도라멕틴, 에피노멕틴, 목시덱틴,
(8) METI I 화합물 : 페나자퀸, 피리다벤, 테부펜피라드, 톨펜피라드, 플루페네림, 하이드라메틸논, 펜피록시메이트, 피리미디펜, 디코폴 ;
(9) METI II 및 III 화합물 : 아세퀴노실, 플루아시프림, 로테논 ;
(10) 탈공액제 화합물 : 클로르페나피르, 바이나파크릴, 디노부톤, 디노카프, DNOC ;
(11) 산화적 인산화 저해제 화합물 : 시헥사틴, 디아펜티우론, 펜부타틴·옥사이드, 프로파르지트, 아조사이클로틴 ;
(12) 탈피 교란 화합물 : 시프로마진 ;
(13) 혼합 기능 옥시다아제 저해제 화합물 : 피페로닐부톡사이드 ;
(14) 나트륨 채널 차단제 화합물 : 인독사카르브, 메타플루미존 ;
(15) 미생물 농약 : BT 제, 곤충 병원 바이러스제, 곤충 병원 사상균제, 선충 병원 사상균제 ; 바실러스속종, 브베리아균, 검은굳음병균, 페킬로마이세스속종, 튜린지엔신, 버티실리움속종 ;
(16) 라트로필린 수용체 작용약 : 뎁시펩티드, 고리형 뎁시펩티드, 24 원자 고리형 뎁시펩티드, 에모뎁시드 ;
(17) 옥토파민성 작용약 : 아미트라즈 ;
(18) 리아노진 유도체 작용약 : 플루벤디아미드, 클로란트라닐리프롤, 시안트라닐리프롤
(19) 마그네슘 자극성 ATP 아제의 저해약 : 티옥사이클람, 티오술탑, 네레이스 톡신 ;
(20) 섭식 저해약 : 피메트로딘
(21) 진드기 성장 저해약 : 클로펜테진, 에톡사졸 ;
(22) 그 밖의 것 : 벤클로티아즈, 비페나제이트, 피리다릴, 황, 디에노피라펜, 시플루메토펜, 아미드플루메트, 테트라디폰, 클로르디메포름, 1,3-디클로로프로펜, DCIP, 페니소브로모레이트, 벤조메이트, 메타알데히드, 스피네토람, 피리플루퀴나존, 벤족시메이트, 브로모프로필레이트, 퀴노메티오네이트, 클로르펜질레이트, 클로르피크린, 클로티아조벤, 디시클라닐, 페녹사크림, 펜트리파닐, 플루벤지민, 플루펜진, 가십플루어 (gossyplure), 재패닐루어 (Japonilure), 메톡사디아존, 석유, 올레산칼륨, 술플루라미드, 테트라술, 트리아라센 ;
살균제 :
(1) 벤조이미다졸계 : 베노밀, 카르벤다짐, 프베리다졸, 티아벤다졸, 티오파네이트 메틸 등 ;
(2) 디카르복시이미드계 ; 클로졸리네이트, 이프로디온, 프로시미돈, 빈크로졸린 등 ;
(3) DMI-살균제계 : 이마잘릴, 옥스포코나졸, 페푸라조에이트, 프로클로라즈, 트리플루미졸, 트리포린, 피리페녹스, 페나리몰, 누아리몰, 아자코나졸, 비텔타놀, 브롬코나졸, 시프로코나졸, 디페노코나졸, 디니코나졸, 에폭시코나졸, 펜브코나졸, 플루퀸코나졸, 플루실라졸, 플루트리아홀, 헥사코나졸, 이미벤코나졸, 이프코나졸, 메트코나졸, 미크로부타닐, 펜코나졸, 프로피코나졸, 프로티오코나졸, 시메코나졸, 테부코나졸, 테트라코나졸, 트리아디메폰, 트리아디메놀, 트리티코나졸, 에타코나졸, 파코나졸시스 등 ;
(4) 페닐아미드계 : 베나락실, 플라락실, 메타락실, 메타락실-M, 옥사딕실, 오푸라세 등 ;
(5) 아민계 : 알디모르프, 도데모르프, 펜프로피모르프, 트리데모르프, 펜프로피딘, 피페랄린, 스피로옥사민 등 ;
(6) 포스포로티올레이트계 : EDDP, 이프로벤포스, 피라조포스 등 ;
(7) 디티올란계 : 이소프로티올란 등 ;
(8) 카르복사미드 : 베노다닐, 보스칼리드, 카르복신, 펜푸란, 플루톨라닐, 플라메토필, 메프로닐, 옥시카르복신, 펜티오피라드, 티플루자미드 등 ;
(9) 하이드록시-(2-아미노)피리미딘계 : 부피리메이트, 디메티리몰, 에티리몰 등 ;
(10) AP 살균제 (아닐리노피리미딘) 계 : 시프로지닐, 메파니피림, 피리메타닐 등 ;
(11) N-페닐카바메이트계 : 디에토펜카르브 등 ;
(12) QoI-살균제 (Qo 저해제) 계 : 아족시스트로빈, 피콕시스트로빈, 피라크로스트로빈, 크레속심-메틸, 트리플록시스트로빈, 디목시스트로빈, 메토미노스트로빈, 오리자스트로빈, 파목사돈, 플루옥사스트로빈, 펜아미돈, 메토미노펜 등 ;
(13) PP 살균제 (페닐피롤) 계 : 펜피코닐, 플루디옥소닐 등 ;
(14) 퀴놀린계 : 퀴녹사펜 등 ;
(15) AH 살균제 (방향족 탄화수소) 계 : 비페닐, 클로로네브, 디클로란, 퀸토젠, 테크나젠, 톨크토포스-메틸 등 ;
(16) MBI-R 계 : 프사라이드, 피로퀼론, 트리시크라졸 등 ;
(17) MBI-D 계 : 카르프로파미드, 디클로시메트, 페녹사닐 등 ;
(18) SBI 제 : 펜헥사미드, 피리부티카르브, 터비나핀 등 ;
(19) 페닐우레아 : 펜시클론 등 ;
(20) QiI-살균제 (Qi 저해제) : 시아조파미드 등 ;
(21) 벤즈아미드계 : 족사미드 등 ;
(22) 에노피란우론계 : 블라스트사이딘, 밀디오마이신 등 ;
(23) 헥소피라노실계 : 카스가마이신 등 ;
(24) 글루코피라노실계 : 스트렙토마이신, 발리다마이신 등 ;
(25) 시아노아세트아미드계 : 시목사닐 등 ;
(26) 카바메이트계 : 이도카르브, 프로파모카르브, 프로티오카르브, 폴리카바메이트 등 ;
(27) 탈공액제 : 비나파크릴, 디노캡, 페림존, 플루아지남 등 ;
(28) 유기 주석 화합물 : 아세트산트리페닐주석, 염화트리페닐주석, 수산화트리페닐주석 등 ;
(29) 인산에스테르 : 아인산, 트리클로포스메틸, 포세틸 등 ;
(30) 프탈아미드산계 : 테크로프탈람 등 ;
(31) 벤조트리아진계 : 트리아족사이드 등 ;
(32) 벤젠술포나미드계 : 플루술파미드 등 ;
(33) 피리다지논 : 디클로메진 등 ;
(34) CAA 살균제 (카르복실산아미드) 계 : 디메토모르프, 플루모르프, 벤티아발리카르브, 이프로발리카르브, 만지프로파미드 등 ;
(35) 테트라사이클린 : 옥시테트라사이클린 등 ;
(36) 티오카바메이트계 : 메타술포카르브 등 ;
(37) 그 밖의 화합물 : 에트리디아졸, 폴리옥신, 옥소리닉산, 하이드록시이소옥사졸, 옥티놀린, 실티오팜, 디플루메토림, 아시벤조랄 S 메틸, 프로베나졸, 티아지닐, 에타복삼, 시플루페나미드, 프로퀴나지드, 메트라페논, 플루오피콜라이드, 수산화제2구리, 유기 구리, 황, 파밤, 만제브, 만네브, 메티람, 프로피네브, 티우람, 지네브, 지람, 캡탄, 켑타폴, 폴펫, 클로로탈로닐, 디클로플루아니드, 톨릴플루아니드, 도딘, 구아자틴, 이미노크타딘아세트산염, 이미노크타딘도데실벤젠술폰산염, 아닐라진, 디티아논, 클로로피크린, 다조메트, 메탐나트륨염, 퀴노메티오네이트, 시프로프람, 실티오팜, 아그로박테리움, 플루오로이미드 등 ;
식물 성장 조절제 :
아부시딘산, 인돌부티르산, 우니코나졸, 에티클로제이트, 에테폰, 클로시포낙, 클로르메쿼트, 클로렐라 추출액, 과산화칼슘, 시아나미드, 디클로르프롭, 지베렐린, 다미노지드, 데실알코올, 트리넥사팍에틸, 메피쿼트클로라이드, 파크로부토라졸, 파라핀 왁스, 피페로닐부톡사이드, 피라플루펜에틸, 플루르프리미돌, 프로하이드로자스몬, 프로헥사디온칼슘염, 벤질아미노푸린, 펜디메타린, 포클로르페누론, 말레산하이드라지드칼륨, 1-나프틸아세트아미드, 4-CPA, MCPB, 콜린, 황산옥시퀴놀린, 에티클로제이트, 부트랄린, 1-메틸시클로프로펜, 아비글리신염산염 ;
실시예
다음으로, 실시예를 나타내어 본 발명을 더욱 구체적으로 설명한다. 단, 본 발명은 이하의 실시예에 의해 하등 제한되는 것은 아니다.
실시예 1
(i) 1-(3-Bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea 의 제조
[화학식 18]
Phenyl 3-bromo-5-chlorophenoxycarbamate (3.00 g) 를 테트라하이드로푸란 (50 ㎖) 에 용해하였다. 이것에 쿠밀아민 (1.54 g) 및 트리에틸아민 (1.15 g) 을 첨가하여, 가열 환류하 5 시간 교반하였다. 그 후, 반응 용매를 감압 증류 제거하였다. 얻어진 잔류물을 실리카 겔 칼럼 크로마토그래피 (전개 용매 ; 헥산 : 아세트산에틸 = 3 : 1) 로 조 (粗) 정제하였다. 얻어진 미정제 결정을 헥산으로 세정하여, 1-(3-Bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea (2.89 g, 수율 86 %) 을 얻었다.
1-(3-Bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea 의 물성은 다음과 같았다.
(ii) 1-(3-Bromo-5-chlorophenoxy)-1-ethyl-3-(2-phenylpropan-2-yl)urea (화합물 번호 1-24) 의 제조
[화학식 19]
1-(3-Bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea (2.89 g) 를 N,N-디메틸포름아미드 (30 ㎖) 에 용해하였다. 이것에 탄산칼륨 (5.18 g) 및 요오드에탄 (1.17 g) 을 첨가하여, 실온에서 하룻밤 교반하였다. 그 후, 아세트산에틸을 첨가하였다. 염화암모늄 수용액으로 세정하고, 유기층을 황산마그네슘으로 건조시켰다. 여과 후, 용매를 감압 증류 제거하였다. 얻어진 잔류물을 실리카 겔 칼럼 크로마토그래피 (전개 용매 ; 헥산 : 아세트산에틸 = 5 : 1) 로 정제하여, 목적으로 하는 1-(3-Bromo-5-chlorophenoxy)-1-ethyl-3-(2-phenylpropan-2-yl)urea (2.86 g, 수율 92 %) 를 얻었다.
1-(3-Bromo-5-chlorophenoxy)-1-ethyl-3-(2-phenylpropan-2-yl)urea 의 물성은 다음과 같았다.
전술한 방법 등에 의해 제조할 수 있는 본 발명의 아릴옥시우레아 화합물의 예를 표 1 ∼ 4 에 나타낸다. 표 1 은 식 (a) 로 나타내는 화합물 중의 치환기를 나타낸다. 표 2 는 식 (b) 로 나타내는 화합물 중의 치환기를 나타낸다. 표 3 은 식 (c) 로 나타내는 화합물 중의 치환기를 나타낸다. 표 4 는 식 (d) 로 나타내는 화합물 중의 치환기를 나타낸다. 또, 표 1 ∼ 4 는 상기한 방법 등에 의해 제조할 수 있는 본 발명의 아릴옥시우레아 화합물의 일부를 나타낸 것에 불과하다. 본 명세서에 있어서 구체적으로 나타낼 수 없던 다른 화합물, 즉 본 발명의 취지와 범위에서 벗어나지 않는 각종 기로 치환된 것을 상기 방법 등에 의해서 제조할 수 있으며 또한 사용할 수 있음은 본 명세서의 기재에 의해 당업자에게 있어서 용이하게 이해될 수 있는 것이다.
[화학식 20]
[화학식 21]
[화학식 22]
[화학식 23]
표 1 ∼ 3 에 나타낸 화합물 중, 점조 (粘稠) 한 오일인 것 (Visc. oil 또는 vis), 또는 아모르퍼스인 것 (Amorphous 또는 amo) 에 관해서는, 1H-NMR (CDCl3) 을 측정하였다. 그 측정 결과를 하기에 나타낸다.
또한, 본 발명의 아릴옥시우레아 화합물의 제조 중간체의 예를 표 5 ∼ 9 에 나타낸다. 표 5 는 식 (e) 로 나타내는 제조 중간체의 예를 나타낸다. 표 6 은 식 (f) 로 나타내는 제조 중간체의 예를 나타낸다. 표 7 은 식 (d) 로 나타내는 제조 중간체의 예를 나타낸다. 표 8 은 식 (g) 로 나타내는 제조 중간체의 예를 나타낸다.
[화학식 24]
[화학식 25]
[화학식 26]
[화학식 27]
표 5 ∼ 9 에 나타낸 화합물 중, 하기 화합물 번호의 화합물에 관해서 1H-NMR (DCl3) 을 측정하였다. 그 측정 결과를 하기에 나타낸다.
본 발명의 유해 생물 방제제의 제제 실시예를 약간 나타내는데, 첨가물 및 첨가 비율이 이들 실시예로 한정되어야 하는 것은 아니며, 광범위하게 변화시키는 것이 가능하다. 제제 실시예 중의 부는 중량부를 나타낸다. 이하에 농원예용의 제제 실시예를 나타낸다.
제제 실시예 1 (수화제)
본 발명 화합물 40 부
규조토 53 부
고급 알코올황산에스테르 4 부
알킬나프탈렌술폰산염 3 부
이상을 균일하게 혼합하고 미세하게 분쇄하여, 유효 성분 40 % 의 수화제를 얻었다.
제제 실시예 2 (유제)
본 발명 화합물 30 부
자일렌 33 부
디메틸포름아미드 30 부
폴리옥시에틸렌알킬알릴에테르 7 부
이상을 혼합 용해하여, 유효 성분 30 % 의 유제를 얻었다.
이하에 방역용·동물용의 제제 실시예를 나타낸다.
제제 실시예 3 (과립)
본 발명 화합물 5 부
카올린 94 부
화이트카본 1 부
본 발명 화합물을 유기 용매 중에서 용해시키고, 담체 위로 분무한 후, 용매를 감압하에 증발시킨다. 이 종류의 과립은 동물의 모이와 혼합할 수 있다.
제제 실시예 4 (주입제)
본 발명 화합물 0.1 ∼ 1 부
낙화생유 밸런스
조제 후에는 멸균 필터에 의해 여과 멸균한다.
제제 실시예 5 (푸어-온제)
본 발명 화합물 5 부
미리스트산에스테르 10 부
이소프로판올 밸런스
제제 실시예 6 (스폿온제)
본 발명 화합물 10 ∼ 15 부
팔미트산에스테르 10 부
이소프로판올 밸런스
제제 실시예 7 (스프레이온제)
본 발명 화합물 1 부
프로필렌글리콜 10 부
이소프로판올 밸런스
[생물 시험]
본 발명 화합물이 살진드기제의 유효 성분으로서 유용한 것을 이하의 시험예로 나타낸다.
시험예 1 점박이응애 (Tetranychus urticae) 에 대한 효력 시험
3 호 화분에 파종한 강낭콩의 발아 후 7 ∼ 10 일이 경과된 초생엽 상에 유기 인제 저항성의 점박이응애 암컷 성충을 10 마리 접종하였다. 이어서, 상기 제제 실시예 2 에 나타낸 처방의 유제를 조제하였다. 이 유제를 화합물 농도 125 ppm 이 되도록 물로 희석하고, 그 희석액을 상기 강낭콩에 살포하였다. 그 강낭콩을, 온도 25 ℃, 습도 65 % 의 항온실 내에 두었다. 살포로부터 3 일 경과 후에 성충의 생사를 조사하였다. 살포로부터 14 일 경과 후에 산란된 알이 성충까지 발육할 수 있었는지 여부를 조사하였다.
화합물 번호 1-3, 1-10, 1-20, 1-21, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-39, 1-41, 1-42, 1-50, 1-51, 1-54, 1-55, 1-56, 1-57, 1-60, 1-61, 1-62, 1-63, 1-65, 1-66, 1-67, 1-68, 1-71, 1-94, 1-96, 1-97, 1-98, 1-99, 1-101, 1-102, 1-103, 1-108, 1-109, 1-110, 1-111, 1-114, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-129, 1-130, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-140, 1-149, 1-152, 1-160, 1-161, 1-171, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-209, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-220, 1-221, 1-222, 1-223, 1-224, 1-226, 1-227, 1-228, 1-229, 1-230, 1-232, 1-233, 1-234, 1-235, 1-236, 1-237, 2-1, 2-2, 2-4, 2-6, 2-7, 2-8, 2-10, 2-11, 2-13, 2-24, 2-26, 2-33, 2-37, 2-39, 2-40, 2-42, 2-44, 2-46, 2-47, 2-50, 2-51, 2-52, 2-53, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-71, 2-72, 3-3, 및 3-22 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 125 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
시험예 2 귤응애 (Panonychus citri) 에 대한 효력 시험
샤알레에 넣은 귤잎 상에 가나가와현산의 귤응애 암컷 성충을 8 마리 접종하였다. 이어서 상기 제제 실시예 2 에 나타낸 처방의 유제를 조제하였다. 이 유제를 화합물 농도 125 ppm 이 되도록 물로 희석하고, 그 희석액을 회전 살포탑으로 상기 귤에 살포하였다. 그 귤을 온도 25 ℃, 습도 65 % 의 항온실 내에 두었다. 살포로부터 3 일 경과 후에 성충의 생사를 조사하였다. 살포로부터 10 일 경과 후에 산란된 알이 성충까지 발육할 수 있었는지 여부를 조사하였다.
화합물 번호 1-3, 1-8, 1-10, 1-24, 1-50, 1-110, 1-111, 1-114, 1-116, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-129, 1-134, 1-135, 1-149, 1-152, 1-161, 1-171, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-192, 1-193, 1-194, 1-197, 1-199, 1-200, 1-201, 1-202, 1-204, 1-205, 1-206, 1-207, 1-209, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-220, 1-222, 1-224, 1-227, 1-229, 1-230, 1-233, 1-234, 1-235, 1-236, 1-237, 2-1, 2-2, 2-4, 2-6, 2-7, 2-10, 2-11, 2-21, 2-33, 2-37, 2-39, 2-40, 2-44, 2-50, 2-51, 2-52, 2-53, 2-55, 2-56, 2-57, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 및 2-71 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 125 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
시험예 3 귤응애 (Panonychus citri) 에 대한 효력 시험
샤알레에 넣은 귤잎 상에 와카야마현산의 살진드기제 저항성의 귤응애 암컷 성충을 8 마리 접종하였다. 이어서 상기 제제 실시예 2 에 나타낸 처방의 유제를 조제하였다. 이 유제를 화합물 농도 125 ppm 이 되도록 물로 희석하고, 그 희석액을 회전 살포탑으로 상기 귤에 살포하였다. 그 귤을 온도 25 ℃, 습도 65 % 의 항온실 내에 두었다. 살포로부터 3 일 경과 후에 성충의 생사를 조사하였다. 살포로부터 10 일 경과 후에 산란된 알이 성충까지 발육할 수 있었는지 여부를 조사하였다.
화합물 번호 1-20, 1-26, 1-27, 1-28, 1-29, 1-35, 1-41, 1-42, 1-51, 1-60, 1-61, 1-63, 1-65, 1-66, 1-67, 1-68, 1-98, 1-99, 1-101, 1-116, 1-124, 1-161, 1-186, 1-189, 1-230, 2-8, 2-13, 2-26, 및 2-50 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 125 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
시험예 4 차응애 (Tetranychus kanzawai) 에 대한 효력 시험
3 호 화분에 파종한 강낭콩의 발아 후 7 ∼ 10 일이 경과된 초생엽 상에 오카야마현산의 차응애 암컷 성충을 10 마리 접종하였다. 이어서, 상기 제제 실시예 2 에 나타낸 처방의 유제를 조제하였다. 이 유제를 화합물 농도 500 ppm 또는 125 ppm 이 되도록 물로 희석하고, 그 희석액을 상기 강낭콩에 살포하였다. 그 강낭콩을 온도 25 ℃, 습도 65 % 의 항온실 내에 두었다. 살포로부터 3 일 경과 후에 성충의 생사를 조사하였다. 살포로부터 14 일 경과 후에, 산란된 알이 성충까지 발육할 수 있었는지 여부를 조사하였다.
화합물 번호 1-8, 1-10, 1-11, 1-13, 1-16, 1-19, 1-20, 1-21, 1-24, 1-26, 1-27, 1-28, 1-29, 1-30, 1-41, 1-42, 1-43, 1-46, 1-47, 1-48, 1-56, 1-57, 1-58, 1-60, 1-61, 1-62, 1-63, 1-67, 1-66, 1-71, 1-74, 1-80, 1-94, 1-95, 1-96, 1-98, 1-100, 1-102, 1-104, 1-106, 1-108, 1-109, 1-110, 1-111, 1-115, 1-118, 1-119, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-131, 1-140, 1-144, 1-209, 1-212, 1-218, 1-220, 1-224, 1-225, 1-232, 1-234, 1-235, 1-236, 2-12, 2-22, 2-23, 2-24, 2-34, 2-41, 2-47, 2-55, 2-56, 3-2, 3-3, 3-4, 및 4-5 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 500 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
화합물 번호 1-3, 1-25, 1-39, 1-40, 1-50, 1-51, 1-53, 1-55, 1-64, 1-65, 1-66, 1-68, 1-93, 1-97, 1-99, 1-101, 1-103, 1-114, 1-116, 1-120, 1-129, 1-130, 1-132, 1-135, 1-136, 1-137, 1-149, 1-150, 1-152, 1-161, 1-162, 1-171, 1-177, 1-178, 1-179, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-211, 1-213, 1-214, 1-215, 1-216, 1-222, 1-223, 1-226, 1-227, 1-228, 1-229, 1-230, 1-233, 1-237, 2-5, 2-6, 2-8, 2-10, 2-13, 2-21, 2-26, 2-33, 2-37, 2-39, 2-40, 2-42, 2-44, 2-46, 2-50, 2-51, 2-52, 2-53, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-71, 2-72, 2-76 및 3-22 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 125 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
시험예 5 귤녹진드기 (Aculops pelekassi) 에 대한 효력 시험
샤알레에 넣은 귤잎 상에, 살진드기제 저항성 귤녹진드기 성충을 20 마리 접종하였다. 이어서 상기 제제 실시예 2 에 나타낸 처방의 유제를 조제하였다. 이 유제를 화합물 농도 125 ppm 이 되도록 물로 희석하고, 그 희석액을 회전 살포탑으로 상기 귤에 살포하였다. 그 귤을 온도 25 ℃, 습도 65 % 의 항온실 내에 두었다. 살포로부터 3 일 경과 후에 성충의 생사를 조사하였다. 살포로부터 10 일 경과 후에 산란된 알이 성충까지 발육할 수 있었는지 여부를 조사하였다.
화합물 번호 1-3, 1-8, 1-9, 1-10, 1-13, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-41, 1-42, 1-50, 1-51, 1-55, 2-1, 2-2, 2-4, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-13, 2-21, 2-24, 및 2-33 의 화합물을 각각 함유하는 유제에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 농도 125 ppm 으로 희석한 경우에 있어서의 살충률이 90 % 이상이었다.
시험예 6 작은소참진드기 (Haemaphysalis longicornis) 에 대한 살충 시험
20 ㎖ 용량의 유리 바이알병에, 본 발명 화합물의 농도 400 ppm 의 아세톤 용액 0.118 ㎖ 를 첨가하였다. 유리 바이알병을 회전시키면서 유리 바이알병 내부에 드라이어로 송풍하여, 아세톤을 휘발시키고 박막을 바이알병 내벽에 제작하였다. 사용한 유리 바이알병의 내벽의 표면적은 47 ㎠ 이기 때문에, 처리약량은 1 ㎍/㎠ 가 된다.
이 바이알병 안에, 작은소참진드기의 어린 진드기를 15 ∼ 40 마리 풀어놓고, 뚜껑을 닫아 항온실 (25 ℃, 암흑하) 에 수용하였다.
1 일 경과 후 및 2 일 경과 후에 사충 (死蟲) 수를 조사하여, 이하의 계산식으로부터 사충률을 산출하였다.
사충률 (%) = (죽은 참진드기수)/(시험에 사용된 참진드기수)×100
화합물 번호 1-161, 2-1, 2-13, 및 2-26 의 화합물에 관해서 상기 시험을 실시하였다. 그 결과, 모든 화합물이 사충률이 100 % 였다.
이상의 결과로부터, 본 발명 화합물은 진드기에 대하여 우수한 살작용 (殺作用) 을 나타내는 것을 알 수 있다.
산업상 이용가능성
본 발명의 아릴옥시우레아 화합물 또는 그 염은 농작물이나 위생면에서 문제가 되는 유해 생물을 방제할 수 있다. 특히 진드기류 및/또는 식물 병원균류를 효과적으로 방제할 수 있다.
Claims (4)
- 식 (I) 로 나타내는 아릴옥시우레아 화합물 또는 그 염.
상기 식 (I) 중,
Cy 는 C6∼10 아릴기, 또는 헤테로아릴기를 나타낸다.
X 는 비치환의 C1∼6 알킬기, C3∼8 시클로알킬 C1~6 알킬기, C1∼6 할로알킬기, 하이드록시 C1∼6 알킬기, C1∼6 알콕시 C1∼6 알킬기, C2∼6 알케닐옥시 C1∼6 알킬기, 헤테로아릴옥시 C1∼6 알킬기, C1∼7 아실옥시 C1∼6 알킬기, 카르복실기 C1∼6 알킬기, C1∼6 알콕시카르보닐 C1∼6 알킬기, C1∼7 아실아미노 C1∼6 알킬기, C1∼6 알킬아미노카르보닐 C1∼6 알킬기, C1∼6 알콕시카르보닐아미노 C1∼6 알킬기, C7∼11 아르알킬기, C6∼10 아릴카르보닐아미노 C1∼6 알킬기, 비치환의 C3∼8 시클로알킬기, 비치환의 C2∼6 알케닐기, C2∼6 할로알케닐기, 비치환의 C2∼6 알키닐기, C2∼6 할로알키닐기, 수산기, 비치환의 C1∼6 알콕시기, C1∼6 할로알콕시기, 아미노기, 비치환의 C1∼6 알킬아미노기, 비치환의 C1∼7 아실기, 할로겐 치환 C1∼7 아실기, 비치환의 C1∼6 알콕시카르보닐기, C3∼8 시클로알킬 C1∼6 알콕시카르보닐기, C1∼6 할로알콕시카르보닐기, 비치환의 C1∼6 알킬술포닐기, 비치환의 C1∼6 알콕시술포닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 하이드록시이미노 C1∼6 알킬기, C1∼6 알콕시이미노 C1∼6 알킬기, C3∼8 시클로알킬 C1~6 알콕시이미노 C1∼6 알킬기, C7∼11 아르알킬옥시이미노 C1∼6 알킬기, 니트로기, 시아노기, 또는 할로겐 원자를 나타낸다.
n 은 Cy 상의 X 의 개수를 나타내며 또한 0 ∼ 5 중 어느 정수이다. n 이 2 이상일 때, X 는 서로 동일하거나 상이해도 된다. 또한, n 이 2 이상일 때, X 는 하나가 되어 결합하는 탄소 원자 또는 질소 원자와 함께 고리를 형성해도 된다.
R1 은 비치환의 C1∼6 알킬기, 비치환의 C2∼6 알케닐기, 비치환의 C2∼6 알키닐기를 나타낸다.
Q 는 식 (II) 로 나타내는 기를 나타낸다.
상기 식 (II) 중,
* 는 결합 위치를 나타낸다.
R2 는 수소 원자, 비치환의 C1∼6 알킬기, 비치환의 C2∼6 알케닐기, 비치환의 C2∼6 알키닐기, 비치환의 C1∼7 아실기, 또는, 비치환의 C1∼6 알콕시카르보닐기를 나타내고,
R3 및 R4 는 각각 독립적으로 비치환의 C1∼6 알킬기를 나타낸다. 여기서, R3 과 R4 는 하나가 되어 결합하는 탄소 원자와 함께 고리를 형성해도 된다.
R5 는 비치환의 아미노카르보닐기, C1∼6 알킬아미노카르보닐기 ; 디C1∼6 알킬아미노카르보닐기 ; C3∼8 시클로알킬아미노카르보닐기 ; C2∼6 알키닐아미노카르보닐기 ; 페닐아미노카르보닐기, N-페닐-N-메틸아미노카르보닐기 ; C1∼6 알콕시 C1∼6 알킬아미노카르보닐기; C1∼6 할로알킬아미노카르보닐기, C3∼8 시클로알킬 C1∼6 알킬아미노카르보닐기 ; C7∼11 아르알킬아미노카르보닐기; 1 위치 치환-고리형 아민카르보닐기 ; 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 또는 비치환의 혹은 치환기를 갖는 헤테로아릴기를 나타낸다.
상기 X 및 R5 에 있어서의, 치환기를 갖는 C6∼10 아릴기 및 치환기를 갖는 헤테로아릴기에 있어서의 치환기는, 할로겐 원자, C1∼6 알킬기, C1∼6 할로알킬기기 또는 시아노기이다.
상기 Cy, X 및 R5 에 있어서의, 헤테로아릴기는, 고리를 구성하는 원자로서 탄소 원자 이외에 질소 원자, 산소 원자 및 황 원자에서 선택되는 1 ∼ 4 개의 복소 원자를 포함하는 5 ∼10 원자의 아릴기이다.
Z 는 산소 원자를 나타낸다. - 식 (I) 로 나타내는 아릴옥시우레아 화합물 또는 그 염.
상기 식 (I) 중,
Cy 는 C6∼10 아릴기, 또는 헤테로아릴기를 나타낸다.
X 는 비치환의 C1∼6 알킬기, C3∼8 시클로알킬 C1~6 알킬기, C1∼6 할로알킬기, 하이드록시 C1∼6 알킬기, C1∼6 알콕시 C1∼6 알킬기, C2∼6 알케닐옥시 C1∼6 알킬기, 헤테로아릴옥시 C1∼6 알킬기, C1∼7 아실옥시 C1∼6 알킬기, 카르복실기 C1∼6 알킬기, C1∼6 알콕시카르보닐 C1∼6 알킬기, C1∼7 아실아미노 C1∼6 알킬기, C1∼6 알킬아미노카르보닐 C1∼6 알킬기, C1∼6 알콕시카르보닐아미노 C1∼6 알킬기, C7∼11 아르알킬기, C6∼10 아릴카르보닐아미노 C1∼6 알킬기, 비치환의 C3∼8 시클로알킬기, 비치환의 C2∼6 알케닐기, C2∼6 할로알케닐기, 비치환의 C2∼6 알키닐기, C2∼6 할로알키닐기, 수산기, 비치환의 C1∼6 알콕시기, C1∼6 할로알콕시기, 아미노기, 비치환의 C1∼6 알킬아미노기, 비치환의 C1∼7 아실기, 할로겐 치환 C1∼7 아실기, 비치환의 C1∼6 알콕시카르보닐기, C3∼8 시클로알킬 C1~6 알콕시카르보닐기, C1∼6 할로알콕시카르보닐기, 비치환의 C1∼6 알킬술포닐기, 비치환의 C1∼6 알콕시술포닐기, 비치환의 혹은 치환기를 갖는 C6∼10 아릴기, 비치환의 혹은 치환기를 갖는 헤테로아릴기, 비치환의 하이드록시이미노 C1∼6 알킬기, C1∼6 알콕시이미노 C1∼6 알킬기, C3∼8 시클로알킬 C1~6 알콕시이미노 C1∼6 알킬기, C7∼11 아르알킬옥시이미노 C1∼6 알킬기, 니트로기, 시아노기, 또는 할로겐 원자를 나타낸다.
상기 치환기를 갖는 C6∼10 아릴기 및 상기 치환기를 갖는 헤테로아릴기에 있어서의 치환기는, 할로겐 원자, C1∼6 알킬기, C1∼6 할로알킬기 또는 시아노기이다.
n 은 Cy 상의 X 의 개수를 나타내며 또한 0 ∼ 5 중 어느 정수이다. n 이 2 이상일 때, X 는 서로 동일하거나 상이해도 된다. 또한, n 이 2 이상일 때, X 는 하나가 되어 결합하는 탄소 원자 또는 질소 원자와 함께 고리를 형성해도 된다.
R1 은 비치환의 C1∼6 알킬기, 비치환의 C2∼6 알케닐기, 비치환의 C2∼6 알키닐기를 나타낸다.
Q 는 식 (II) 로 나타내는 기를 나타낸다.
상기 식 (II) 중,
* 는 결합 위치를 나타낸다.
R2 는 수소 원자, 비치환의 C1∼6 알킬기, 비치환의 C2∼6 알케닐기, 비치환의 C2∼6 알키닐기, 비치환의 C1∼7 아실기, 또는 비치환의 C1∼6 알콕시카르보닐기를 나타내고,
R3 및 R4 는 각각 독립적으로 비치환의 C1∼6 알킬기를 나타낸다. 여기서, R3 과 R4 는 하나가 되어 결합하는 탄소 원자와 함께 고리를 형성해도 된다.
R5 는 치환기를 갖는 페닐기, 치환기를 갖는 피리딜기, 치환기를 갖는 피라지닐기, 치환기를 갖는 피리미디닐기 또는 치환기를 갖는 피리다지닐기를 나타낸다.
Z 는 산소 원자를 나타낸다. - 제 1 항 또는 제 2 항에 기재된 아릴옥시우레아 화합물 또는 그 염에서 선택되는 적어도 1 종을 유효 성분으로서 함유하는 살진드기제.
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