JP5280972B2 - Acaricides and new urea compounds - Google Patents
Acaricides and new urea compounds Download PDFInfo
- Publication number
- JP5280972B2 JP5280972B2 JP2009191045A JP2009191045A JP5280972B2 JP 5280972 B2 JP5280972 B2 JP 5280972B2 JP 2009191045 A JP2009191045 A JP 2009191045A JP 2009191045 A JP2009191045 A JP 2009191045A JP 5280972 B2 JP5280972 B2 JP 5280972B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- phenyl
- halogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000642 acaricide Substances 0.000 title claims abstract description 41
- 230000000895 acaricidal effect Effects 0.000 title abstract description 41
- 150000003672 ureas Chemical class 0.000 title description 2
- -1 urea compound Chemical class 0.000 claims abstract description 174
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 125000005843 halogen group Chemical group 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 239000004480 active ingredient Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 16
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000005109 alkynylthio group Chemical group 0.000 claims description 12
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003441 thioacyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000005108 alkenylthio group Chemical group 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 239000004202 carbamide Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000012043 crude product Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 0 *c(c(N(*)C(N(*)*)=O)c1)cc(I=*)c1S* Chemical compound *c(c(N(*)C(N(*)*)=O)c1)cc(I=*)c1S* 0.000 description 6
- 241000193830 Bacillus <bacterium> Species 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052570 clay Inorganic materials 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- SAMVRRMUPIZILL-UHFFFAOYSA-N 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)aniline Chemical compound CC1=CC(F)=C(N)C=C1SCC(F)(F)F SAMVRRMUPIZILL-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241001454295 Tetranychidae Species 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000005846 Triadimenol Substances 0.000 description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
- 229960000490 permethrin Drugs 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 4
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 3
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 2
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- KPTMFLKIYHWQPB-UHFFFAOYSA-N 3,3,4,4-tetrafluoropyrrolidine;hydrochloride Chemical compound Cl.FC1(F)CNCC1(F)F KPTMFLKIYHWQPB-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000006042 4-hexenyl group Chemical group 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000006043 5-hexenyl group Chemical group 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 239000005727 Amisulbrom Substances 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005884 Beta-Cyfluthrin Substances 0.000 description 2
- 239000005740 Boscalid Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- 239000005946 Cypermethrin Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000005795 Imazalil Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000005796 Ipconazole Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000005813 Penconazole Substances 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 description 2
- KVIZNNVXXNFLMU-AIIUZBJTSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1r,3r)-2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@@H]1\C=C\C KVIZNNVXXNFLMU-AIIUZBJTSA-N 0.000 description 2
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 2
- GDZNYEZGJAFIKA-UHFFFAOYSA-N acetoprole Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 2
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000001923 cyclic compounds Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- 229960005424 cypermethrin Drugs 0.000 description 2
- 125000004783 dichloromethoxy group Chemical group ClC(O*)Cl 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229960002125 enilconazole Drugs 0.000 description 2
- 230000000967 entomopathogenic effect Effects 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- HICUREFSAIZXFQ-JOWPUVSESA-N i9z29i000j Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\[C@H](OC(=O)C(=N/OC)\C=1C=CC=CC=1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 HICUREFSAIZXFQ-JOWPUVSESA-N 0.000 description 2
- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000974 larvacidal effect Effects 0.000 description 2
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 229960003536 phenothrin Drugs 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- DJQOGYTZMZEXJN-UHFFFAOYSA-N pyrrolidine-1-carbothioamide Chemical compound NC(=S)N1CCCC1 DJQOGYTZMZEXJN-UHFFFAOYSA-N 0.000 description 2
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(e)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000006373 (C2-C10) alkyl group Chemical group 0.000 description 1
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- BKBSMMUEEAWFRX-NBVRZTHBSA-N (E)-flumorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(F)=CC=1)=C\C(=O)N1CCOCC1 BKBSMMUEEAWFRX-NBVRZTHBSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- IKNXXTIMVROREQ-WXXKFALUSA-N (e)-but-2-enedioic acid;[2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl]-imidazol-1-ylmethanone Chemical compound OC(=O)\C=C\C(O)=O.C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1.C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 IKNXXTIMVROREQ-WXXKFALUSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- 125000006013 1,1-difluoroethoxy group Chemical group 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical class NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical group C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 1
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- QDFVXXBCJYNKKC-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-cyclopropylbutyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CCCC(C=1C=CC(Cl)=CC=1)C1CC1 QDFVXXBCJYNKKC-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- ASMNSUBMNZQTTG-UHFFFAOYSA-N 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1CC(C)CCN1C1=C(C=2C(=CC(F)=CC=2F)F)C(Cl)=NC2=NC=NN12 ASMNSUBMNZQTTG-UHFFFAOYSA-N 0.000 description 1
- BIHPYCDDPGNWQO-UHFFFAOYSA-N 5-iai Chemical compound C1=C(I)C=C2CC(N)CC2=C1 BIHPYCDDPGNWQO-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- VSVKOUBCDZYAQY-UHFFFAOYSA-N 7-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1SN=C2 VSVKOUBCDZYAQY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 239000005651 Acequinocyl Substances 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- 239000005652 Acrinathrin Substances 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- ITULYNYDLFPRGX-UHFFFAOYSA-N C1(CC1)C(=O)NC1=C(C=C(C(=C1)SCC(F)(F)F)C)F Chemical compound C1(CC1)C(=O)NC1=C(C=C(C(=C1)SCC(F)(F)F)C)F ITULYNYDLFPRGX-UHFFFAOYSA-N 0.000 description 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- QDJSUBRWVPEKCM-UHFFFAOYSA-N Cc(cc(c(N=C=O)c1)F)c1SCC(F)(F)F Chemical compound Cc(cc(c(N=C=O)c1)F)c1SCC(F)(F)F QDJSUBRWVPEKCM-UHFFFAOYSA-N 0.000 description 1
- JRBBGLNQOMQGPK-UHFFFAOYSA-N Cc(cc(c(NC(N(CC1(F)F)CC1(F)F)=O)c1)F)c1SCC(F)(F)F Chemical compound Cc(cc(c(NC(N(CC1(F)F)CC1(F)F)=O)c1)F)c1SCC(F)(F)F JRBBGLNQOMQGPK-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 239000005887 Chromafenozide Substances 0.000 description 1
- SKJLCARKPODHGI-UHFFFAOYSA-N ClC1=C(NC=C1)C1=CC=CC2=CC3=CC=CC=C3C=C12 Chemical compound ClC1=C(NC=C1)C1=CC=CC2=CC3=CC=CC=C3C=C12 SKJLCARKPODHGI-UHFFFAOYSA-N 0.000 description 1
- 239000005654 Clofentezine Substances 0.000 description 1
- 101710151559 Crystal protein Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- 239000005644 Dazomet Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005762 Dimoxystrobin Substances 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- MVJSVXQVGBDZIX-UHFFFAOYSA-N FC1(CN(CC1(F)F)C(=O)N(C)C1=C(C=C(C(=C1)SCC(F)(F)F)C)F)F Chemical compound FC1(CN(CC1(F)F)C(=O)N(C)C1=C(C=C(C(=C1)SCC(F)(F)F)C)F)F MVJSVXQVGBDZIX-UHFFFAOYSA-N 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005900 Flonicamid Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005782 Fluopicolide Substances 0.000 description 1
- 239000005783 Fluopyram Substances 0.000 description 1
- 239000005784 Fluoxastrobin Substances 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- ULCWZQJLFZEXCS-KGLIPLIRSA-N Furconazole-cis Chemical compound O1[C@@H](OCC(F)(F)F)CC[C@@]1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ULCWZQJLFZEXCS-KGLIPLIRSA-N 0.000 description 1
- 239000005903 Gamma-cyhalothrin Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000179420 Haemaphysalis longicornis Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 101000663831 Homo sapiens SH3 and PX domain-containing protein 2A Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 239000005907 Indoxacarb Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005914 Metaflumizone Substances 0.000 description 1
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005808 Metalaxyl-M Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- 241000907681 Morpho Species 0.000 description 1
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- OKEAHVREANYBGJ-UHFFFAOYSA-N N=[S+]C#N Chemical compound N=[S+]C#N OKEAHVREANYBGJ-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- 239000005818 Picoxystrobin Substances 0.000 description 1
- 239000005924 Pirimiphos-methyl Substances 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 239000005825 Prothioconazole Substances 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005926 Pyridalyl Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 229930001406 Ryanodine Natural products 0.000 description 1
- RSYLOLFPBDLKRL-UHFFFAOYSA-N S1(C=CC=C1)=O.S1(C=CC=C1)=O.ClC=CCCl Chemical compound S1(C=CC=C1)=O.S1(C=CC=C1)=O.ClC=CCCl RSYLOLFPBDLKRL-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical group C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 239000005870 Ziram Substances 0.000 description 1
- 239000005863 Zoxamide Substances 0.000 description 1
- GBAWQJNHVWMTLU-RQJHMYQMSA-N [(1R,5S)-7-chloro-6-bicyclo[3.2.0]hepta-2,6-dienyl] dimethyl phosphate Chemical compound C1=CC[C@@H]2C(OP(=O)(OC)OC)=C(Cl)[C@@H]21 GBAWQJNHVWMTLU-RQJHMYQMSA-N 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- QSGNQELHULIMSJ-POHAHGRESA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] dimethyl phosphate Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl QSGNQELHULIMSJ-POHAHGRESA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical compound N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical group C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- YLFSVIMMRPNPFK-WEQBUNFVSA-N acrinathrin Chemical compound CC1(C)[C@@H](\C=C/C(=O)OC(C(F)(F)F)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YLFSVIMMRPNPFK-WEQBUNFVSA-N 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- 150000005245 cyanopyrroles Chemical class 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 description 1
- 229950000775 cyromazine Drugs 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- YEJGPFZQLRMXOI-PKEIRNPWSA-N diclocymet Chemical compound N#CC(C(C)(C)C)C(=O)N[C@H](C)C1=CC=C(Cl)C=C1Cl YEJGPFZQLRMXOI-PKEIRNPWSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 1
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 description 1
- 229950006719 fluazuron Drugs 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 description 1
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 1
- GNVDAZSPJWCIQZ-UHFFFAOYSA-N flusulfamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GNVDAZSPJWCIQZ-UHFFFAOYSA-N 0.000 description 1
- KGXUEPOHGFWQKF-ZCXUNETKSA-N flutianil Chemical compound COC1=CC=CC=C1N(CCS\1)C/1=C(C#N)/SC1=CC(C(F)(F)F)=CC=C1F KGXUEPOHGFWQKF-ZCXUNETKSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- RPOCFUQMSVZQLH-UHFFFAOYSA-N furan-2,5-dione;2-methylprop-1-ene Chemical compound CC(C)=C.O=C1OC(=O)C=C1 RPOCFUQMSVZQLH-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 102000057479 human SH3PXD2A Human genes 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical class [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- YNKFZRGTXAPYFD-UHFFFAOYSA-N n-[[2-chloro-3,5-bis(trifluoromethyl)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1Cl YNKFZRGTXAPYFD-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical class CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical class NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 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
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000001228 spectrum Methods 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
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 150000003536 tetrazoles Chemical class 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
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical group O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical group S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-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
- 230000005068 transpiration Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は、殺ダニ剤、並びに殺ダニ剤の有効成分として有用な新規ウレア化合物及びその塩に関する。 The present invention relates to an acaricide, a novel urea compound useful as an active ingredient of an acaricide, and a salt thereof.
従来、多数の殺ダニ剤が使用されているが、その効力が不十分であったり、薬剤抵抗性問題によりその使用が制限されたり、また、植物体に薬害や汚染を生じたり、あるいは人畜魚類等に対する毒性が強かったりすることから、必ずしも満足すべき殺ダニ剤とは言い難いものが少なくない。従って、かかる欠点の少ない安全に使用できる新しい殺ダニ剤の開発が要望されている。 Many acaricides have been used in the past, but their effectiveness is insufficient, their use is restricted due to drug resistance problems, phytotoxicity and contamination of plants, and human fish In many cases, it is not always a satisfactory acaricide because of its high toxicity. Accordingly, there is a demand for the development of a new acaricide that can be used safely and has few such drawbacks.
本発明に関連して、特許文献1には、本発明化合物と類似した骨格を有する化合物が記載されている。
しかしながら、この文献には、その化合物が殺ダニ活性を有する旨や、本発明化合物については記載されていない。
However, this document does not describe that the compound has acaricidal activity or the compound of the present invention.
本発明は、効果が確実で安全に使用できる殺ダニ剤、並びに殺ダニ剤の有効成分として有用な新規ウレア化合物及びその塩を提供することを課題とする。 This invention makes it a subject to provide the novel urea compound useful as an active ingredient of an acaricide, an acaricide which is reliable and can be used safely, and its salt.
本発明者らは上記課題を解決すべく鋭意研究した結果、下記式(I)で示される化合物が優れた殺ダニ活性を有することを見出し、本発明を完成するに至った。
すなわち、本発明は第1に、式(I)
As a result of intensive studies to solve the above problems, the present inventors have found that a compound represented by the following formula (I) has an excellent acaricidal activity, and have completed the present invention.
That is, the present invention firstly has the formula (I)
〔式中、R1は、C1〜20アルキル基又はC1〜20ハロアルキル基を表す。
R2は、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。
[Wherein, R 1 represents a C1-20 alkyl group or a C1-20 haloalkyl group.
R 2 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C2 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, unsubstituted or substituted C1-20 A thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted group Aryloxy group, unsubstituted or substituted heteroyloxy group, unsubstituted Or a substituted C1-20 alkylthio group, an unsubstituted or substituted C2-20 alkenylthio group, an unsubstituted or substituted C2-20 alkynylthio group, an unsubstituted or substituted arylthio group, Unsubstituted or substituted heteroylthio group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, none A substituted or substituted arylsulfonyl group or an unsubstituted or substituted heterocyclic group is represented.
R3は、水素原子、ハロゲン原子、ニトロ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。 R 3 represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 2- 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, unsubstituted or substituted C1-20 A thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted group Aryloxy group, unsubstituted or substituted heteroyloxy group, unsubstituted Or a substituted C1-20 alkylthio group, an unsubstituted or substituted C2-20 alkenylthio group, an unsubstituted or substituted C2-20 alkynylthio group, an unsubstituted or substituted arylthio group, Unsubstituted or substituted heteroylthio group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, none A substituted or substituted arylsulfonyl group or an unsubstituted or substituted heterocyclic group is represented.
R4は、水素原子、シアノ基、ホルミル基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC1〜20アシル基、又は、無置換若しくは置換基を有するフェニル基を表す。
R5は、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するアミノ基、式(a)
R 4 is a hydrogen atom, a cyano group, a formyl group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 acyl group, or an unsubstituted or substituted phenyl group Represents.
R 5 represents an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted amino group, the formula (a)
で表される、無置換若しくは置換基を有する含窒素ヘテロ環基、式(b) An unsubstituted or substituted nitrogen-containing heterocyclic group represented by formula (b)
(式中、R8、R9はそれぞれ独立して、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC3〜6シクロアルキル基、C2〜6アルケニル基、無置換若しくは置換基を有するフェニル基、又は無置換若しくは置換基を有するヘテロ環基を表す。又は、R8とR9が一緒になって結合して、窒素原子、酸素原子、又は硫黄原子を1〜4個含んでいてもよい3〜8員のへテロ環を形成する。)で表される基、無置換若しくは置換基を有するピロリジン−2−イル基、無置換若しくは置換基を有するフェニル基、無置換若しくは置換基を有するC3〜8シクロアルキル基、又は、無置換若しくは置換基を有するC1〜20アルキルチオ基を表す。 (In the formula, R 8 and R 9 are each independently an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-6 cycloalkyl group, a C2-6 alkenyl group, an unsubstituted group. Or a substituted phenyl group, or an unsubstituted or substituted heterocyclic group, or R 8 and R 9 are bonded together to form a nitrogen atom, an oxygen atom, or a sulfur atom; A 4- to 8-membered hetero ring which may contain 4), a pyrrolidin-2-yl group having an unsubstituted or substituted group, a phenyl group having an unsubstituted or substituted group, An unsubstituted or substituted C3-8 cycloalkyl group or an unsubstituted or substituted C1-20 alkylthio group is represented.
Xは、式:N−CNで表される基、又は式:N−OR’(R’は水素原子又は無置換若しくは置換基を有するC1〜20アルキル基を示す。)で表される基を表す。
nは0〜2のいずれかの整数を表し、mは0〜2のいずれかの整数を表す。但し、m+n≦2である。
X represents a group represented by the formula: N—CN, or a group represented by the formula: N—OR ′ (R ′ represents a hydrogen atom or an unsubstituted or substituted C1-20 alkyl group). Represent.
n represents any integer of 0 to 2, and m represents any integer of 0 to 2. However, m + n ≦ 2.
Aは酸素原子、硫黄原子、又は、式:N−Q(Qは、シアノ基、無置換若しくは置換基を有するC1〜20アルキル基、又は式:OR10で表される基を示す。R10は、水素原子、無置換若しくは置換基を有するC1〜10アルキル基を表す。)で表される基を示す。〕で示される化合物又はその塩の少なくとも一種を有効成分として含有することを特徴とする殺ダニ剤を提供する。
本発明は第2に、式(I−1)
A represents an oxygen atom, a sulfur atom, or a group represented by the formula: NQ (Q is a cyano group, an unsubstituted or substituted C1-20 alkyl group, or a formula: OR 10 ; R 10. Represents a hydrogen atom, an unsubstituted or substituted C1-10 alkyl group having a substituent. ] An acaricide which contains at least one of the compounds represented by the above or a salt thereof as an active ingredient.
Secondly, the present invention relates to the formula (I-1)
(式中、R1は、C1〜20アルキル基又はC1〜20ハロアルキル基を表す。
R21は、無置換又は置換基を有するC1〜20アルキル基を表す。
R3は、水素原子、ハロゲン原子、ニトロ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。
(In the formula, R 1 represents a C1-20 alkyl group or a C1-20 haloalkyl group.
R 21 represents an unsubstituted or substituted C1-20 alkyl group.
R 3 represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 2- 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, unsubstituted or substituted C1-20 A thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted group Aryloxy group, unsubstituted or substituted heteroyloxy group, unsubstituted Or a substituted C1-20 alkylthio group, an unsubstituted or substituted C2-20 alkenylthio group, an unsubstituted or substituted C2-20 alkynylthio group, an unsubstituted or substituted arylthio group, Unsubstituted or substituted heteroylthio group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, none A substituted or substituted arylsulfonyl group or an unsubstituted or substituted heterocyclic group is represented.
R4は、水素原子、シアノ基、ホルミル基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC1〜20アシル基、又は、無置換若しくは置換基を有するフェニル基を表す。
R6、R7はそれぞれ独立して、水素原子、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アルコキシ基、又は、無置換若しくは置換基を有するC1〜20アルキルチオ基を表す。また、R6、R7は一緒になって、無置換若しくは置換基を有する環を形成してもよい。さらに、該環は、環内に、式:−N(R4)−C(=O)−で表される基に結合する窒素原子以外にヘテロ原子を含んでいてもよい。)
で示されるウレア化合物又はその塩を提供する。
R 4 is a hydrogen atom, a cyano group, a formyl group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 acyl group, or an unsubstituted or substituted phenyl group Represents.
R 6 and R 7 are each independently a hydrogen atom, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C2-20 alkenyl group, an unsubstituted or substituted C2-20. An alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted C1-20 alkoxy group, or an unsubstituted or substituted C1-20 alkylthio group is represented. R 6 and R 7 may be combined to form an unsubstituted or substituted ring. Furthermore, the ring may contain a hetero atom in addition to the nitrogen atom bonded to the group represented by the formula: —N (R 4 ) —C (═O) —. )
The urea compound shown by these, or its salt is provided.
本発明によれば、効果が確実で安全に使用できる殺ダニ剤、並びに殺ダニ剤の有効成分として有用な新規ウレア化合物及びその塩が提供される。 ADVANTAGE OF THE INVENTION According to this invention, the novel aurea compound and its salt useful as an active ingredient of an acaricide which an effect is reliable and can be used safely are provided.
以下、本発明を詳細に説明する。
本発明の第1は、前記式(I)で示される化合物(以下、「化合物(I)」ということがある。)又はその塩の少なくとも一種を有効成分として含有することを特徴とする殺ダニ剤である。
Hereinafter, the present invention will be described in detail.
According to a first aspect of the present invention, the acaricide is characterized by containing as an active ingredient at least one of the compounds represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”) or a salt thereof. It is an agent.
(1)化合物(I)
式(I)中、R1は、C1〜20アルキル基又はC1〜20ハロアルキル基を表す。
R1のC1〜20アルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、i−ブチル基、s−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−デシル基等が挙げられる。
(1) Compound (I)
In formula (I), R 1 represents a C1-20 alkyl group or a C1-20 haloalkyl group.
Examples of the C1-20 alkyl group of R 1 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, and n-pentyl. Group, n-hexyl group, n-heptyl group, n-octyl group, n-decyl group and the like.
R1のC1〜20ハロアルキル基としては、フルオロメチル基、クロロメチル基、ブロモメチル基、ジフルオロメチル基、ジクロロメチル基、ジブロモメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、2,2,2−トルフルオロエチル基、2,2,2−トリクロロエチル基、ペンタフルオロエチル基等が挙げられる。
これらの中でも、R1としては、C1〜20ハロアルキル基が好ましく、C1〜6ハロアルキル基がより好ましく、C1〜6フルオロアルキル基が更に好ましい。
Examples of the C1-20 haloalkyl group for R 1 include a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, 2, Examples include 2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group and the like.
Among these, R 1, preferably a C1~20 haloalkyl group, more preferably a C1~6 haloalkyl group, more preferably C1~6 fluoroalkyl group.
R2は、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基(アシル基の炭素数はカルボニル基の炭素原子を除いた炭素原子の数である。以下にて同じ。)、無置換若しくは置換基を有するC1〜20チオアシル基(チオアシル基の炭素数はチオカルボニル基の炭素原子を除いた炭素原子の数である。以下にて同じ。)、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。 R 2 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C2 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group (acyl group is carbon number of carbonyl group) This is the number of carbon atoms excluding atoms. The same applies hereinafter.), C1-20 thioacyl group having no substituent or substituent (the carbon number of the thioacyl group is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group) The same shall apply hereinafter.), C1-20 alkoxy group having an unsubstituted or substituted group, C2-20 having an unsubstituted or substituted group. An alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted heteroyloxy group, an unsubstituted or substituted C1 ~ 20 alkylthio groups, unsubstituted or substituted C2-20 alkenylthio groups, unsubstituted or substituted C2-20 alkynylthio groups, unsubstituted or substituted arylthio groups, unsubstituted or substituted heteroylthio groups Group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, unsubstituted or substituted arylsulfonyl Group or unsubstituted young Ku represents a heterocyclic group having a substituent.
R2のハロゲン原子としては、フッ素原子、塩素原子、臭素原子等が挙げられる。
無置換若しくは置換基を有するアミノ基としては、アミノ基;メチルアミノ基、エチルアミノ基等のモノC1〜C6アルキルアミノ基;ジメチルアミノ基、ジエチルアミノ基等のジC1〜C6アルキルアミノ基;アセチルアミノ基、ベンゾイルアミノ基等のアシルアミノ基;フェニルアミノ基、4−メチルフェニルアミノ基等の置換基を有していてもよいフェニルアミノ基;等が挙げられる。
Examples of the halogen atom for R 2 include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the unsubstituted or substituted amino group include an amino group; a mono C1-C6 alkylamino group such as a methylamino group and an ethylamino group; a diC1-C6 alkylamino group such as a dimethylamino group and a diethylamino group; Groups, acylamino groups such as benzoylamino groups; phenylamino groups optionally having substituents such as phenylamino groups and 4-methylphenylamino groups; and the like.
無置換若しくは置換基を有するC1〜20アルキル基のC1〜20アルキル基としては、前記R1で例示したのと同様のものが挙げられる。 The C1~20 alkyl group C1~20 alkyl group having unsubstituted or substituted, the same ones as exemplified for R 1 can be mentioned.
無置換若しくは置換基を有するC2〜20アルケニル基のC2〜20アルケニル基としては、ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等が挙げられる。 Examples of the C2-20 alkenyl group of the unsubstituted or substituted C2-20 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1 -Methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl- Examples include 2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
無置換若しくは置換基を有するC2〜20アルキニル基のC2〜20アルキニル基としては、エチニル基、1−プロピニル基、プロパルギル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−メチル−2−プロピニル基、2−メチル−3−ブチニル基、1−ペンチニル基、2−ペンチニル基、3−ペンチニル基、4−ペンチニル基、1−メチル−2−ブチニル基、2−メチル−3−ペンチニル基、1−ヘキシニル基、1,1−ジメチル−2−ブチニル基等が挙げられる。 Examples of the C2-20 alkynyl group of the unsubstituted or substituted C2-20 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl 2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3- A pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned.
C1〜20アルキル基、C2〜20アルケニル基、C2〜20アルキニル基の置換基としては、フッ素原子、塩素原子等のハロゲン原子;メトキシ基、エトキシ基等のC1〜6アルコキシ基;フェニル基、4−メチルフェニル基等の無置換若しくは置換基を有するアリール基;等が挙げられる。 Substituents for C1-20 alkyl group, C2-20 alkenyl group, C2-20 alkynyl group include halogen atoms such as fluorine atom and chlorine atom; C1-6 alkoxy groups such as methoxy group and ethoxy group; phenyl group, 4 -An unsubstituted or substituted aryl group such as a methylphenyl group;
無置換若しくは置換基を有するアリール基のアリール基としては、フェニル基、1−ナフチル基、2−ナフチル基等が挙げられる。 Examples of the aryl group of the unsubstituted or substituted aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
無置換若しくは置換基を有するC1〜20アシル基のC1〜20アシル基としては、アセチル基、プロピオニル基等のC1〜20アルキルカルボニル基(アルキルカルボニル基の炭素数はカルボニル基の炭素原子を除いた炭素原子の数である。);アリルカルボニル基、クロチルカルボニル基等のC2〜20アルケニルカルボニル基(アルケニルカルボニル基の炭素数はカルボニル基の炭素原子を除いた炭素原子の数である。);プロパルギルカルボニル基等のC2〜20アルキニルカルボニル基(アルキニルカルボニル基の炭素数はカルボニル基の炭素原子を除いた炭素原子の数である。);ベンゾイル基等のアリールカルボニル基;等が挙げられる。 The C1-20 acyl group of an unsubstituted or substituted C1-20 acyl group is a C1-20 alkylcarbonyl group such as an acetyl group or a propionyl group (the carbon number of the alkylcarbonyl group excludes the carbon atom of the carbonyl group) C2-20 alkenylcarbonyl groups such as allylcarbonyl group, crotylcarbonyl group, etc. (the carbon number of the alkenylcarbonyl group is the number of carbon atoms excluding the carbon atom of the carbonyl group); C2-20 alkynylcarbonyl group such as propargylcarbonyl group (the carbon number of alkynylcarbonyl group is the number of carbon atoms excluding the carbon atom of carbonyl group); arylcarbonyl group such as benzoyl group; and the like.
無置換若しくは置換基を有するC1〜20チオアシル基のC1〜20チオアシル基としては、チオアセチル基、チオプロピオニル基等のC1〜20アルキルチオカルボニル基(アルキルチオカルボニル基の炭素数はチオカルボニル基の炭素原子を除いた炭素原子の数である。);アリルチオカルボニル基、クロチルチオカルボニル基等のC2〜20アルケニルチオカルボニル基(アルケニルチオカルボニル基の炭素数はチオカルボニル基の炭素原子を除いた炭素原子の数である。);プロパルギルチオカルボニル基等のC2〜20アルキニルチオカルボニル基(アルキニルチオカルボニル基の炭素数はチオカルボニル基の炭素原子を除いた炭素原子の数である。);チオベンゾイル基等のアリールチオカルボニル基;等が挙げられる。 The C1-20 thioacyl group of an unsubstituted or substituted C1-20 thioacyl group includes a C1-20 alkylthiocarbonyl group such as a thioacetyl group or a thiopropionyl group (the carbon number of the alkylthiocarbonyl group is the carbon atom of the thiocarbonyl group). C2-20 alkenylthiocarbonyl group such as allylthiocarbonyl group, crotylthiocarbonyl group, etc. (The carbon number of the alkenylthiocarbonyl group is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group.) A C2-20 alkynylthiocarbonyl group such as a propargylthiocarbonyl group (the carbon number of the alkynylthiocarbonyl group is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group); a thiobenzoyl group, etc. Arylthiocarbonyl group; and the like.
無置換若しくは置換基を有するC1〜20アルコキシ基のC1〜20アルコキシ基としては、メトキシ基、エトキシ基、n−プロポキシ基、i−プロポキシ基、n−ブトキシ基、t−ブトキシ基等が挙げられる。 Examples of the C1-20 alkoxy group of the unsubstituted or substituted C1-20 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, and a t-butoxy group. .
無置換若しくは置換基を有するC2〜20アルケニルオキシ基のC2〜20アルケニルオキシ基としては、アリルオキシ基、クロチルオキシ基等が挙げられる。
無置換若しくは置換基を有するC2〜20アルキニルオキシ基のC2〜20アルキニルオキシ基としては、プロパルギルオキシ基等が挙げられる。
Examples of the C2-20 alkenyloxy group of the unsubstituted or substituted C2-20 alkenyloxy group include an allyloxy group and a crotyloxy group.
Examples of the C2-20 alkynyloxy group of the unsubstituted or substituted C2-20 alkynyloxy group include a propargyloxy group.
無置換若しくは置換基を有するアリールオキシ基のアリールオキシ基としては、フェノキシ基、1−ナフチルオキシ基、2−ナフチルオキシ基等が挙げられる。 Examples of the aryloxy group of the unsubstituted or substituted aryloxy group include a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.
無置換若しくは置換基を有するヘテロイルオキシ基のヘテロイルオキシ基としては、2−ピリジルオキシ基、3−ピリジルオキシ基、4−ピリジルオキシ基、2−イミダゾリルオキシ基、4−イミダゾリルオキシ基等が挙げられる。
無置換若しくは置換基を有するC1〜20アルキルチオ基のC1〜20アルキルチオ基としては、メチルチオ基、エチルチオ基、n−プロピルチオ基、i−プロピルチオ基、n−ブチルチオ基、t−ブチルチオ基等が挙げられる。
Examples of the heteroyloxy group of the unsubstituted or substituted heteroyloxy group include 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group, 2-imidazolyloxy group, 4-imidazolyloxy group, and the like. Can be mentioned.
Examples of the C1-20 alkylthio group of the unsubstituted or substituted C1-20 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, and a t-butylthio group. .
無置換若しくは置換基を有するC2〜20アルケニルチオ基のC2〜20アルケニルチオ基としては、アリルチオ基、クロチルチオ基等が挙げられる。
無置換若しくは置換基を有するC2〜20アルキニルチオ基のC2〜20アルキニルチオ基としては、プロパルギルチオ基等が挙げられる。
Examples of the C2-20 alkenylthio group of the unsubstituted or substituted C2-20 alkenylthio group include an allylthio group and a crotylthio group.
Examples of the C2-20 alkynylthio group of the unsubstituted or substituted C2-20 alkynylthio group include a propargylthio group.
無置換若しくは置換基を有するアリールチオ基のアリールチオ基としては、フェニルチオ基、1−ナフチルチオ基、2−ナフチルチオ基等が挙げられる。
無置換若しくは置換基を有するヘテロイルチオ基のヘテロイルチオ基としては、2−ピリジルチオ基、3−ピリジルチオ基、4−ピリジルチオ基、2−イミダゾリルチオ基、4−イミダゾリルチオ基等が挙げられる。
Examples of the arylthio group of the unsubstituted or substituted arylthio group include a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.
Examples of the heteroylthio group of the unsubstituted or substituted heteroylthio group include a 2-pyridylthio group, a 3-pyridylthio group, a 4-pyridylthio group, a 2-imidazolylthio group, and a 4-imidazolylthio group.
無置換若しくは置換基を有するC1〜20アルキルスルフィニル基のC1〜20アルキルスルフィニル基としては、メチルスルフィニル基、エチルスルフィニル基等が挙げられる。
無置換若しくは置換基を有するアリールスルフィニル基のアリールスルフィニル基としては、フェニルスルフィニル基、1−ナフチルスルフィニル基、2−ナフチルスルフィニル基等が挙げられる。
Examples of the C1-20 alkylsulfinyl group of the unsubstituted or substituted C1-20 alkylsulfinyl group include a methylsulfinyl group and an ethylsulfinyl group.
Examples of the arylsulfinyl group of the unsubstituted or substituted arylsulfinyl group include a phenylsulfinyl group, a 1-naphthylsulfinyl group, and a 2-naphthylsulfinyl group.
無置換若しくは置換基を有するC1〜20アルキルスルホニル基のC1〜20アルキルスルホニル基としては、メチルスルホニル基、エチルスルホニル基等が挙げられる。
無置換若しくは置換基を有するアリールスルホニル基のアリールスルホニル基としては、フェニルスルホニル基、1−ナフチルスルホニル基、2−ナフチルスルホニル基等が挙げられる。
Examples of the C1-20 alkylsulfonyl group of the unsubstituted or substituted C1-20 alkylsulfonyl group include a methylsulfonyl group and an ethylsulfonyl group.
Examples of the arylsulfonyl group of the unsubstituted or substituted arylsulfonyl group include a phenylsulfonyl group, a 1-naphthylsulfonyl group, and a 2-naphthylsulfonyl group.
また、無置換若しくは置換基を有するヘテロ環基のヘテロ環基としては、環内に、窒素原子、酸素原子及び硫黄原子から選ばれる少なくとも一種の原子を有する、飽和又は不飽和の環状化合物の基が挙げられる。 In addition, the heterocyclic group of an unsubstituted or substituted heterocyclic group includes a saturated or unsaturated cyclic compound group having at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom in the ring. Is mentioned.
具体的には、2−ピリジル基、3−ピリジル基、4−ピリジル基、2−ピリミジル基、4−ピリミジル基、5−ピリミジル基、3−ピリダジル基、4−ピリダジル基、2−(1,3,5−トリアジル)基、3−(1,2,4−トリアジル)基、5−(1,2,4−トリアジル)基、6−(1,2,4−トリアジル)基等の6員環化合物の基;
2−チエニル基、3−チエニル基、2−フリル基、3−フリル基、3−ピラゾリル基、4−ピラゾリル基、5−ピラゾリル基、2−イミダゾリル基、4−イミダゾリル基、5−イミダゾリル基、3−(1,2,4−トリアゾリル)基、5−(1,2,4−トリアゾリル)基、2−ピラジル基、2−チアゾリル基、4−チアゾリル基、5−チアゾリル基、3−イソチアゾリル基、4−イソチアゾリル基、5−イソチアゾリル基、2−(1,3,4−チアジアゾリル)基、3−(1,2,4−チアジアゾリル)基、5−(1,2,4−チアジアゾリル)基、5−(1,2,3−チアジアゾリル)基、2−オキサゾリル基、4−オキサゾリル基、5−オキサゾリル基、3−イソオキサゾリル基、4−イソオキサゾリル基、5−イソオキサゾリル基、2−(1,3,4−オキサジアゾリル)基、3−(1,2,4−オキサジアゾリル)基、5−(1,2,4−オキサジアゾリル)基、5−(1,2,3−オキサジアゾリル)基等の5員環化合物の基;等が挙げられる。
Specifically, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 3-pyridyl group, 4-pyridazyl group, 2- (1, 3,5-triazyl) group, 3- (1,2,4-triazyl) group, 5- (1,2,4-triazyl) group, 6- (1,2,4-triazyl) group, etc. A group of ring compounds;
2-thienyl group, 3-thienyl group, 2-furyl group, 3-furyl group, 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 2-imidazolyl group, 4-imidazolyl group, 5-imidazolyl group, 3- (1,2,4-triazolyl) group, 5- (1,2,4-triazolyl) group, 2-pyrazyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group 4-isothiazolyl group, 5-isothiazolyl group, 2- (1,3,4-thiadiazolyl) group, 3- (1,2,4-thiadiazolyl) group, 5- (1,2,4-thiadiazolyl) group, 5- (1,2,3-thiadiazolyl) group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, -(1,3,4-oxadiazolyl) group, 3- (1,2,4-oxadiazolyl) group, 5- (1,2,4-oxadiazolyl) group, 5- (1,2,3-oxadiazolyl) group And the like, and the like.
前記C1〜20アシル基(アリールカルボニル基を除く)、C1〜20チオアシル基、C1〜20アルコキシ基、C2〜20アルケニルオキシ基、C2〜20アルキニルオキシ基、C1〜20アルキルチオ基、C2〜20アルケニルチオ基、C2〜20アルキニルチオ基、C1〜20アルキルスルフィニル基、C1〜20アルキルスルホニル基の置換基としては、フッ素原子、塩素原子、臭素原子等のハロゲン原子;フェニル基、4−メチルフェニル基等の無置換若しくは置換基を有するアリール基;等が挙げられる。 C1-20 acyl group (excluding arylcarbonyl group), C1-20 thioacyl group, C1-20 alkoxy group, C2-20 alkenyloxy group, C2-20 alkynyloxy group, C1-20 alkylthio group, C2-20 alkenyl Examples of the substituent for the thio group, C2-20 alkynylthio group, C1-20 alkylsulfinyl group, C1-20 alkylsulfonyl group include halogen atoms such as fluorine atom, chlorine atom, bromine atom; phenyl group, 4-methylphenyl group An unsubstituted or substituted aryl group such as;
前記アリール基、アリールカルボニル基、アリールオキシ基、ヘテロイルオキシ基、アリールチオ基、ヘテロイルチオ基、アリールスルフィニル基、アリールスルホニル基、ヘテロ環基の置換基としては、メチル基、エチル基等のC1〜6アルキル基;トリフルオロメチル基等のC1〜6ハロアルキル基;フッ素原子、塩素原子、臭素原子等のハロゲン原子;メトキシ基、エトキシ基等のC1〜6アルコキシ基;フェニル基、4−メトキシフェニル基等の無置換若しくは置換基を有するアリール基;ニトロ基;等が挙げられる。 Examples of the substituent of the aryl group, arylcarbonyl group, aryloxy group, heteroyloxy group, arylthio group, heteroylthio group, arylsulfinyl group, arylsulfonyl group, and heterocyclic group include C1-6 such as methyl group and ethyl group. Alkyl group; C1-6 haloalkyl group such as trifluoromethyl group; halogen atom such as fluorine atom, chlorine atom and bromine atom; C1-6 alkoxy group such as methoxy group and ethoxy group; phenyl group, 4-methoxyphenyl group and the like An unsubstituted or substituted aryl group; a nitro group; and the like.
これらの中でも、R2としては、シアノ基、ニトロ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC1〜20アシル基が好ましく、無置換若しくは置換基を有するC1〜20アルキル基がより好ましく、無置換若しくは置換基を有するC1〜6アルキル基が更に好ましい。 Among these, as R 2 , a cyano group, a nitro group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C1 ~ 20 acyl groups are preferred, unsubstituted or substituted C1-20 alkyl groups are more preferred, and unsubstituted or substituted C1-6 alkyl groups are even more preferred.
R3は、水素原子、ニトロ基、水酸基、メルカプト基、並びに、前記R2と同様の(ハロゲン原子、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基)を表す。
これらの中でも、R3としては、ハロゲン原子が好ましく、フッ素原子が特に好ましい。
R 3 is a hydrogen atom, a nitro group, a hydroxyl group, a mercapto group, and the same as R 2 above (halogen atom, unsubstituted or substituted amino group, unsubstituted or substituted C1-20 alkyl group, Unsubstituted or substituted C2-20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, A substituted or substituted C1-20 thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyl Oxy group, unsubstituted or substituted aryloxy group, unsubstituted or substituted Teloyloxy group, unsubstituted or substituted C1-20 alkylthio group, unsubstituted or substituted C2-20 alkenylthio group, unsubstituted or substituted C2-20 alkynylthio group, unsubstituted or substituted An arylthio group having an unsubstituted or substituted heteroylthio group, an unsubstituted or substituted C1-20 alkylsulfinyl group, an unsubstituted or substituted arylsulfinyl group, an unsubstituted or substituted C1-20 alkyl A sulfonyl group, an unsubstituted or substituted arylsulfonyl group, or an unsubstituted or substituted heterocyclic group).
Among these, as R 3 , a halogen atom is preferable, and a fluorine atom is particularly preferable.
R4は、水素原子、シアノ基、ホルミル基、前記R2と同様の無置換若しくは置換基を有するC1〜20アルキル基、前記R2と同様の無置換又は置換基を有するC1〜20アシル基、又は、無置換若しくは置換基を有するフェニル基を表す。
R4の無置換若しくは置換基を有するフェニル基の置換基としては、前記R2のアリール基等の置換基として例示したのと同様のものが挙げられる。
これらの中でも、R4としては、水素原子、ホルミル基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC1〜20アシル基が好ましく、水素原子、C1〜20アルキル基、C1〜20アシル基がより好ましい。
R 4 is a hydrogen atom, a cyano group, a formyl group, C1-20 alkyl group having the same unsubstituted or substituted with said R 2, C1-20 acyl group having unsubstituted or substituted group similar to the R 2 Or an unsubstituted or substituted phenyl group.
Examples of the substituent of the unsubstituted or substituted phenyl group for R 4 include those exemplified as the substituent for the aryl group of R 2 .
Among these, as R 4 , a hydrogen atom, a formyl group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 acyl group is preferable, and a hydrogen atom, C1-20 alkyl is preferable. Group, a C1-20 acyl group is more preferred.
R5は、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するアミノ基、前記式(a)で表される、無置換若しくは置換基を有する含窒素ヘテロ環基、前記式(b)で表される基、無置換若しくは置換基を有するピロリジン−2−イル基、無置換若しくは置換基を有するフェニル基、無置換若しくは置換基を有するC3〜8シクロアルキル基、又は、無置換若しくは置換基を有するC1〜20アルキルチオ基を表す。 R 5 is an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted nitrogen-containing heterocyclic group represented by the above formula (a), A group represented by the formula (b), an unsubstituted or substituted pyrrolidin-2-yl group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted C3-8 cycloalkyl group, or Represents an unsubstituted or substituted C1-20 alkylthio group.
前記R5の、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するアミノ基、及び、無置換若しくは置換基を有するC1〜20アルキルチオ基としては、前記R2で例示したのと同様の基が挙げられる。また、前記R5の無置換若しくは置換基を有するフェニル基としては、前記R4で例示したのと同様の基が挙げられる。 Wherein the R 5, C1-20 alkyl group having an unsubstituted or substituted group, an amino group having unsubstituted or substituted, and, as the C1-20 alkylthio group having unsubstituted or substituted, exemplified by the R 2 The same groups as mentioned above can be mentioned. Examples of the unsubstituted or substituted phenyl group for R 5 include the same groups as those exemplified for R 4 .
前記R5の、式(a)で表される無置換若しくは置換基を有する含窒素ヘテロ環基(以下、「含窒素へテロ環基(a)」ということがある。)の含窒素ヘテロ環は、環内に1以上の窒素原子を有する、飽和又は不飽和のヘテロ環である。該含窒素ヘテロ環は、窒素原子のほかに酸素原子及び/又は硫黄原子を含んでいてもよく、単環のものであっても、縮合環構造を有するものであっても、架橋構造を有するものであってもよい。 The nitrogen-containing heterocyclic ring of the nitrogen-containing heterocyclic group having an unsubstituted or substituted group represented by the formula (a) (hereinafter sometimes referred to as “nitrogen-containing heterocyclic group (a)”) of R 5 . Is a saturated or unsaturated heterocycle having one or more nitrogen atoms in the ring. The nitrogen-containing heterocycle may contain an oxygen atom and / or a sulfur atom in addition to a nitrogen atom, and has a crosslinked structure, whether it is a monocyclic ring or a condensed ring structure. It may be a thing.
前記含窒素へテロ環基(a)の含窒素ヘテロ環を構成する、窒素原子、酸素原子及び硫黄原子の合計数は、通常1〜4、好ましくは1〜3である。
また、前記含窒素ヘテロ環基(a)の含窒素ヘテロ環を構成する炭素数は10以下であるのが好ましく、1〜8であるのがより好ましい。
The total number of nitrogen atoms, oxygen atoms and sulfur atoms constituting the nitrogen-containing heterocycle of the nitrogen-containing heterocyclic group (a) is usually 1 to 4, preferably 1 to 3.
The number of carbon atoms constituting the nitrogen-containing heterocycle of the nitrogen-containing heterocyclic group (a) is preferably 10 or less, and more preferably 1-8.
前記含窒素ヘテロ環基(a)として、具体的には、下記第1表に掲げるものを例示することができるが、これらに限定されるものではない。なお、窒素原子上及び環を構成する原子上の置換基は省略し、基本的な骨格のみを記載してある。 Specific examples of the nitrogen-containing heterocyclic group (a) include those listed in Table 1 below, but are not limited thereto. The substituents on the nitrogen atom and the atoms constituting the ring are omitted, and only the basic skeleton is shown.
これらの中でも、含窒素ヘテロ環基(a)としては、ピロリジン−1−イルが特に好ましい。 Among these, pyrrolidin-1-yl is particularly preferable as the nitrogen-containing heterocyclic group (a).
含窒素ヘテロ環基(a)の置換基は特に限定されない。例えば、フッ素原子、塩素原子、臭素原子等のハロゲン原子;メチル基、エチル基、トリフルオロメチル基、ベンジル基等の置換基を有していてもよいC1〜6アルキル基;アリル基、3−クロロアリル基等の置換基を有していてもよいC2〜6のアルケニル基;プロパルギル基等の置換基を有していてもよいC2〜6のアルキニル基;フェニル基、4−メチルフェニル基等の置換基を有していてもよいアリール基;ホルミル基; The substituent of the nitrogen-containing heterocyclic group (a) is not particularly limited. For example, a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom; a C1-6 alkyl group which may have a substituent such as a methyl group, an ethyl group, a trifluoromethyl group or a benzyl group; an allyl group; A C2-6 alkenyl group optionally having a substituent such as a chloroallyl group; a C2-6 alkynyl group optionally having a substituent such as a propargyl group; a phenyl group, a 4-methylphenyl group, etc. Aryl group optionally having substituent; formyl group;
アセチル基、トリフルオロアセチル基等の、無置換若しくは置換基を有するC1〜6アルキルカルボニル基;シンナミル基等の、無置換若しくは置換基を有するC2〜6アルケニルカルボニル基;プロパルギルカルボニル基等の、無置換若しくは置換基を有するC2〜6アルキニルカルボニル基;ベンゾイル基、4−クロロベンゾイル基等の、無置換若しくは置換基を有するアリールカルボニル基;チオアセチル基等の、無置換若しくは置換基を有するC1〜6アルキルチオカルボニル基;アリルチオカルボニル基等の、無置換若しくは置換基を有するC2〜6アルケニルチオカルボニル基;プロパルギルチオカルボニル基等の、無置換若しくは置換基を有するC2〜6アルキニルチオカルボニル基;チオベンゾイル基等の、無置換若しくは置換基を有するアリールチオカルボニル基;カルボキシル基;メトキシカルボニル基、エトキシカルボニル基等の、無置換若しくは置換基を有するC1〜6アルコキシカルボニル基;ビニルオキシカルボニル基等の、無置換若しくは置換基を有するC2〜6アルケニルオキシカルボニル基; An unsubstituted or substituted C1-6 alkylcarbonyl group such as an acetyl group or a trifluoroacetyl group; an unsubstituted or substituted C2-6 alkenylcarbonyl group such as a cinnamyl group; an unsubstituted such as a propargylcarbonyl group; Substituted or substituted C2-6 alkynylcarbonyl group; benzoyl group, 4-chlorobenzoyl group, etc., unsubstituted or substituted arylcarbonyl group; thioacetyl group, etc., unsubstituted or substituted C1-6 An alkylthiocarbonyl group; an unsubstituted or substituted C2-6 alkenylthiocarbonyl group such as an allylthiocarbonyl group; an unsubstituted or substituted C2-6 alkynylthiocarbonyl group such as a propargylthiocarbonyl group; thiobenzoyl A group or the like, unsubstituted or An arylthiocarbonyl group having a substituent; a carboxyl group; a C1-6 alkoxycarbonyl group having an unsubstituted or substituted group such as a methoxycarbonyl group or an ethoxycarbonyl group; an unsubstituted or substituted group such as a vinyloxycarbonyl group A C2-6 alkenyloxycarbonyl group;
プロパルギルオキシカルボニル基等の、無置換若しくは置換基を有するC2〜6のアルキニルオキシカルボニル基;フェノキシカルボニル基、2,4−ジクロロフェノキシカルボニル基等の、無置換若しくは置換基を有するアリールオキシカルボニル基;シアノ基;アミノ基、ジメチルアミノ基、アセチルアミノ基等の、無置換若しくは置換基を有するアミノ基;ニトロ基;水酸基;オキソ基;チオキソ基;メトキシ基、エトキシ基、t−ブトキシ基等の、無置換若しくは置換基を有するC1〜6アルコキシ基;アリルオキシ基、クロチルオキシ基等の、無置換若しくは置換基を有するC2〜6アルケニルオキシ基;プロパルギルオキシ基等の、無置換若しくは置換基を有するC2〜6アルキニルオキシ基;フェノキシ基、4−メチルフェノキシ基等の、無置換若しくは置換基を有するアリールオキシ基;無置換若しくは置換基を有するヘテロイルオキシ基;メルカプト基;メチルチオ基、エチルチオ基等の、無置換若しくは置換基を有するC1〜6アルキルチオ基;アリルチオ基、クロチルチオ基等の、無置換若しくは置換基を有するC2〜6アルケニルチオ基;プロパルギルチオ基等の、無置換若しくは置換基を有するC2〜6アルキニルチオ基;フェニルチオ基等の、無置換若しくは置換基を有するアリールチオ基;無置換若しくは置換基を有するヘテロイルチオ基;メチルスルフィニル基等の、無置換若しくは置換基を有するC1〜6アルキルスルフィニル基;フェニルスルフィニル基等の、無置換若しくは置換基を有するアリールスルフィニル基;メチルスルホニル基等の、無置換若しくは置換基を有するC1〜6アルキルスルホニル基;フェニルスルホニル基等の、無置換若しくは置換基を有するアリールスルホニル基;及び、無置換若しくは置換基を有するヘテロ環基;等が挙げられる。 An unsubstituted or substituted C2-6 alkynyloxycarbonyl group such as a propargyloxycarbonyl group; an unsubstituted or substituted aryloxycarbonyl group such as a phenoxycarbonyl group or a 2,4-dichlorophenoxycarbonyl group; Cyano group; amino group, dimethylamino group, acetylamino group and the like, unsubstituted or substituted amino group; nitro group; hydroxyl group; oxo group; thioxo group; methoxy group, ethoxy group, t-butoxy group, etc. C1-6 alkoxy group having an unsubstituted or substituted group; C2-6 alkenyloxy group having an unsubstituted or substituted group such as an allyloxy group or a crotyloxy group; C2-6 having an unsubstituted or substituted group such as a propargyloxy group 6 alkynyloxy group; phenoxy group, 4-methylpheno C1-6 alkylthio having an unsubstituted or substituted group, such as an aryloxy group having an unsubstituted or substituted group such as a thio group; a heteroyloxy group having an unsubstituted or substituted group; a mercapto group; a methylthio group, an ethylthio group, etc. A group: an unsubstituted or substituted C2-6 alkenylthio group such as an allylthio group or a crotylthio group; an unsubstituted or substituted C2-6 alkynylthio group such as a propargylthio group; a phenylthio group, etc. Substituted or substituted arylthio group; unsubstituted or substituted heteroylthio group; methylsulfinyl group and other unsubstituted or substituted C1-6 alkylsulfinyl groups; phenylsulfinyl group and other unsubstituted or substituted groups Arylsulfinyl group having a methylsulfonyl group, etc. , Cl to 6 alkylsulfonyl group having unsubstituted or substituted; or phenyl sulfonyl group, an arylsulfonyl group having unsubstituted or substituted; and a heterocyclic group having unsubstituted or substituted; and the like.
前記含窒素ヘテロ環基(a)の置換基である、(無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するヘテロ環基)を構成するヘテロ環としては、環内に、窒素原子、酸素原子及び硫黄原子から選ばれる少なくとも一種の原子を有する、飽和又は不飽和の環状化合物が挙げられる。具体的には、イミダゾール、ピラゾール、ピリジン、ピリミジン、ピラジン、ピリダジン、トリアゾール、トリアジン、インドール、インダゾール、プリン、チアジアゾール、オキサジアゾール、キノリン、フタラジン、ナフチリジン、キノキサリン、キナゾリン、シンノリール、プテリジン、アクリジン、フェナントロリン、フェナジン、テトラゾール、チアゾール、オキサゾール、ベンゾイミダゾール、ベンゾオキサゾール、ベンゾチアゾール、インドレニン、テトラザインデン、フラン等の芳香族へテロ環;ピロリジン、ピペリジン、モルホリン、テトラヒドロフラン、テトラヒドロピラン、アジリジン、アゼチジン、オキサゾリジン、ピペラジン、チアゾリジン、トリオキサン等の非芳香族へテロ環;が挙げられる。 A substituent of the nitrogen-containing heterocyclic group (a), (unsubstituted or substituted heteroyloxy group, unsubstituted or substituted heteroylthio group, unsubstituted or substituted heterocyclic group); Examples of the heterocyclic ring to be configured include saturated or unsaturated cyclic compounds having at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom in the ring. Specifically, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, pyridazine, triazole, triazine, indole, indazole, purine, thiadiazole, oxadiazole, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnolele, pteridine, acridine, phenanthroline , Phenazine, tetrazole, thiazole, oxazole, benzimidazole, benzoxazole, benzothiazole, indolenine, tetrazaindene, furan, etc .; pyrrolidine, piperidine, morpholine, tetrahydrofuran, tetrahydropyran, aziridine, azetidine, oxazolidine , Non-aromatic heterocycles such as piperazine, thiazolidine and trioxane.
これらの中でも、含窒素ヘテロ環基(a)の置換基としては、ハロゲン原子、無置換若しくは置換基を有するC1〜6アルキル基が好ましく、ハロゲン原子がより好ましい。
また、含窒素ヘテロ環基(a)は、任意の位置に同一又は相異なって1又は複数個の置換基を有していてもよい。
Among these, as the substituent of the nitrogen-containing heterocyclic group (a), a halogen atom, an unsubstituted or C1-6 alkyl group having a substituent is preferable, and a halogen atom is more preferable.
Moreover, the nitrogen-containing heterocyclic group (a) may have one or a plurality of substituents at the same or different positions.
前記式(b)中、R8、R9はそれぞれ独立して、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC3〜6シクロアルキル基、C2〜6アルケニル基、無置換若しくは置換基を有するフェニル基、又は無置換若しくは置換基を有するヘテロ環基を表す。 In the formula (b), R 8 and R 9 are each independently an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-6 cycloalkyl group, a C2-6 alkenyl group. Represents an unsubstituted or substituted phenyl group, or an unsubstituted or substituted heterocyclic group.
R8、R9の無置換若しくは置換基を有するC1〜6アルキル基のC1〜6アルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、sec−ブチル基、イソブチル基、t−ブチル基等が挙げられる。 The C1~6 alkyl group C1~6 alkyl group having unsubstituted or substituted of R 8, R 9, methyl, ethyl, n- propyl, i- propyl, n- butyl, sec- A butyl group, an isobutyl group, a t-butyl group, etc. are mentioned.
C1〜6アルキル基の置換基としては、フッ素原子、塩素原子、臭素原子等のハロゲン原子;メトキシ基、エトキシ基、クロロメトキシ基、ジクロロメトキシ基、トリクロロメトキシ基、トリフルオロメトキシ基、1−フルオロエトキシ基、1,1−ジフルオロエトキシ基、クロロメトキシ基、ジクロロメトキシ基、トリフルオロメトキシ基等のハロゲンで置換されていてもよいアルコキシ基;等が挙げられる。 Examples of the substituent for the C1-6 alkyl group include halogen atoms such as fluorine atom, chlorine atom, bromine atom; methoxy group, ethoxy group, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoro. And an alkoxy group which may be substituted with a halogen such as ethoxy group, 1,1-difluoroethoxy group, chloromethoxy group, dichloromethoxy group and trifluoromethoxy group.
R8、R9の無置換若しくは置換基を有するC3〜6シクロアルキル基としては、シクロプロピル基、1−メチルシクロプロピル基、2−メチルシクロプロピル基、2,2−ジメチルシクロプロピル基、2−クロロシクロプロピル基、2,2−ジクロロシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。 The C3~6 cycloalkyl group having unsubstituted or substituted of R 8, R 9, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethyl-cyclopropyl group, 2 -Chlorocyclopropyl group, 2,2-dichlorocyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
R8、R9のC2〜6アルケニル基としては、ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等が挙げられる。 The C2~6 alkenyl group of R 8, R 9, a vinyl group, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl group, 1-methyl-2-propenyl group 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1- Examples include a hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.
前記C2〜6アルケニル基の置換基としては、前記C1〜6アルキル基の置換基として例示したのと同様のものが挙げられる。 Examples of the substituent for the C2-6 alkenyl group include those exemplified as the substituent for the C1-6 alkyl group.
R8、R9の、無置換若しくは置換基を有するヘテロ環基のヘテロ環基としては、2−フリル基、3−フリル基、2−チエニル基、3−チエニル基、2−オキサゾリル基、2−オキサゾリニル基、3−イソオキサゾリル基、4−イソオキサゾリル基、5−イソオキサゾリル基、3−イソオキサゾリニル基、2−チアゾリル基、2−チアゾリニル基、3−イソチアゾリル基、3−イソチアゾリニル基、2−ピラニル基、4−テトラヒドロピラニル基、1−アゼチジニル基、2−アゼチジニル基、3−アゼチジニル基、2−ピロリル基、2−ピロリジニル基、2−イミダゾリル基、3−ピラゾリル基、2−イミダゾリニル基、2−ピリジル基、3−ピリジル基、4−ピリジル基、2−ピペリジル基、ピペリジノ基、2−モルホリニル基、モルホリノ基、2−ピペラジニル基、2−ピリミジニル基、3−ピリダジニル基、2−ピラジニル基等が挙げられる。 As the heterocyclic group of unsubstituted or substituted heterocyclic group of R 8 and R 9 , 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-oxazolyl group, 2 -Oxazolinyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 3-isoxazolinyl group, 2-thiazolyl group, 2-thiazolinyl group, 3-isothiazolyl group, 3-isothiazolinyl group, 2-pyranyl Group, 4-tetrahydropyranyl group, 1-azetidinyl group, 2-azetidinyl group, 3-azetidinyl group, 2-pyrrolyl group, 2-pyrrolidinyl group, 2-imidazolyl group, 3-pyrazolyl group, 2-imidazolinyl group, 2 -Pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-piperidyl group, piperidino group, 2-morpholinyl group, morpho Amino group, 2-piperazinyl group, 2-pyrimidinyl group, 3-pyridazinyl group, 2-pyrazinyl group and the like.
R8、R9の、フェニル基、へテロ環基の置換基としては、メチル基、エチル基、n−プロピル基、イソプロピル基等のアルキル基;クロロメチル基、フルオロメチル基、ブロモメチル基、ジクロロメチル基、ジフルオロメチル基、ジブロモメチル基、トリクロロメチル基、トリフルオロメチル基、2,2,2−トリクロロエチル基、2,2,2−トリフルオロエチル基、ペンタフルオロエチル基等のハロアルキル基;メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基等のアルコキシ基;ヒドロキシ基;ニトロ基;シアノ基;アミノ基;メトキシカルボニル基、エトキシカルボニル基、n−プロポキシカルボニル基、イソプロポキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のアルコキシカルボニル基;フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;又は、メタンスルホニル基、エチルスルホニル基、n−プロピルスルホニル基等のアルキルスルホニル基;等が挙げられる。 Examples of substituents for phenyl group and heterocyclic group of R 8 and R 9 include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group; chloromethyl group, fluoromethyl group, bromomethyl group, dichloro A haloalkyl group such as a methyl group, difluoromethyl group, dibromomethyl group, trichloromethyl group, trifluoromethyl group, 2,2,2-trichloroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group; Alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group; hydroxy group; nitro group; cyano group; amino group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, Alkoxycals such as n-butoxycarbonyl group and t-butoxycarbonyl group Alkylsulfonyl group; a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as iodine atom; or a methanesulfonyl group, ethylsulfonyl group, an alkylsulfonyl group such as n- propyl sulfonyl group; and the like.
また、R8とR9は一緒になって結合して、窒素原子、酸素原子、又は硫黄原子を1〜4個含んでいてもよい3〜8員のへテロ環を形成していてもよい。
かかるヘテロ環としては、チオフェン環、テトラヒドロチオフェン環、チオピラン環、テトラヒドロチオピラン環、4−オキサチアン環、チオモルホリン環、1,4−ジチアン環、テトラヒドロチオピラン−4−オン環等が挙げられる。
R 8 and R 9 may be bonded together to form a 3- to 8-membered heterocycle that may contain 1 to 4 nitrogen, oxygen, or sulfur atoms. .
Examples of the heterocycle include a thiophene ring, a tetrahydrothiophene ring, a thiopyran ring, a tetrahydrothiopyran ring, a 4-oxathiane ring, a thiomorpholine ring, a 1,4-dithiane ring, and a tetrahydrothiopyran-4-one ring.
前記R5の、無置換若しくは置換基を有するピロリジン−2−イル基の置換基としては、メチル基等のC1〜6アルキル基;N−t−ブトキシカルボニル基等のエステル基;フッ素原子、塩素原子等のハロゲン原子;等が挙げられる。 Examples of the substituent of the unsubstituted or substituted pyrrolidin-2-yl group of R 5 include a C1-6 alkyl group such as a methyl group; an ester group such as an Nt-butoxycarbonyl group; a fluorine atom, chlorine Halogen atoms such as atoms; and the like.
前記R5の、無置換若しくは置換基を有するC3〜8シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロへキシル基、シクロへプチル基、シクロオクチル基等が挙げられる。
前記C3〜8シクロアルキル基の置換基としては、前記R2のアリール基等の置換基として例示したのと同様の基が挙げられる。
Examples of the unsubstituted or substituted C 3-8 cycloalkyl group represented by R 5 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
Examples of the substituent for the C3-8 cycloalkyl group include the same groups as those exemplified as the substituent for the R 2 aryl group and the like.
Xは、式:N−CNで表される基、又は、式:N−OR’で表される基を表す。式中、R’は、水素原子、又は前記R2で例示したのと同様の、無置換若しくは置換基を有するC1〜20アルキル基を表す。
nは0〜2のいずれかの整数を表し、mは0〜2のいずれかの整数を表す。但し、m+n≦2である。
X represents a group represented by the formula: N—CN or a group represented by the formula: N—OR ′. In the formula, R ′ represents a hydrogen atom or a C1-20 alkyl group having no substituent or a substituent similar to those exemplified for R 2 .
n represents any integer of 0 to 2, and m represents any integer of 0 to 2. However, m + n ≦ 2.
Aは、酸素原子、硫黄原子、又は、式:N−Qで表される基を表す。
式:N−QのQは、シアノ基、無置換若しくは置換基を有するC1〜20アルキル基、又は式:OR10で表される基を示す。
A represents an oxygen atom, a sulfur atom, or a group represented by the formula: NQ.
Wherein: Q of N-Q represents a cyano group, an unsubstituted or C1~20 alkyl group having a substituent group, or the formula: a group represented by OR 10.
Qの、無置換又は置換基を有するC1〜20アルキル基としては、前記R2で例示したのと同様の基が挙げられる。
式:OR10のR10は、水素原子、無置換又は置換基を有するC1〜10アルキル基を表す。
R10の、無置換又は置換基を有するC1〜10アルキル基のC1〜10アルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、i−ブチル基、s−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−デシル基等が挙げられる。その置換基としては、フェニル基、4−メチルフェニル基、2−クロロフェニル基等の無置換若しくは置換基を有するフェニル基等が挙げられる。
本発明の殺ダニ剤においては、化合物(I)が、下記式(Ia)
Examples of the unsubstituted or substituted C1-20 alkyl group for Q include the same groups as those exemplified for R 2 above.
R 10 in the formula: OR 10 represents a hydrogen atom, an unsubstituted or substituted C 1-10 alkyl group having a substituent.
The R 10, examples of C1~10 alkyl groups C1~10 alkyl group having unsubstituted or substituted group, a methyl group, an ethyl group, n- propyl group, i- propyl, n- butyl group, i- butyl , S-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-decyl group and the like. Examples of the substituent include an unsubstituted or substituted phenyl group such as a phenyl group, a 4-methylphenyl group, and a 2-chlorophenyl group.
In the acaricide of the present invention, the compound (I) is represented by the following formula (Ia)
(式中、R1〜R5、A、及びnは前記と同じ意味を表す。)で表される化合物であるのが好ましい。 (Wherein R 1 to R 5 , A, and n represent the same meaning as described above).
(2)本発明化合物(I−1)
本発明の第2は、化合物(I)のうちの、前記式(I−1)で表される、新規なウレア化合物又はその塩(以下、「本発明化合物(I−1)」ということがある。)である。
式(I−1)中、R1、R3及びR4は、前記と同じ意味を表す。
(2) Compound (I-1) of the present invention
A second aspect of the present invention is a novel urea compound represented by the formula (I-1) or a salt thereof (hereinafter referred to as “the present compound (I-1)”) of the compound (I). Yes.)
In formula (I-1), R 1 , R 3 and R 4 represent the same meaning as described above.
R21は、無置換又は置換基を有するC1〜20アルキル基を表す。無置換又は置換基を有するC1〜20アルキル基としては、前記R2の無置換又は置換基を有するC1〜20アルキル基と同様のものが挙げられる。 R 21 represents an unsubstituted or substituted C1-20 alkyl group. Examples of the C1-20 alkyl group having an unsubstituted or substituted group include the same as those of the C2-20 alkyl group having an unsubstituted or substituted R 2 .
R6、R7は、それぞれ独立して、水素原子、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アルコキシ基、又は、無置換若しくは置換基を有するC1〜20アルキルチオ基を表す。 R 6 and R 7 are each independently a hydrogen atom, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 2-20 alkenyl group, an unsubstituted or substituted C 2- A 20 alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted C1-20 alkoxy group, or an unsubstituted or substituted C1-20 alkylthio group is represented.
R6、R7の、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アルコキシ基、又は、無置換若しくは置換基を有するC1〜20アルキルチオ基としては、R2で例示した対応する基と同様のものが挙げられる。 R 6 and R 7 , unsubstituted or substituted C1-20 alkyl group, unsubstituted or substituted C2-20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted C1~20 alkoxy group having an aryl group, unsubstituted or substituted with a group, or, as is C1~20 alkylthio group having unsubstituted or substituted group, the same as those of the corresponding groups exemplified in R 2 It is done.
また、R6、R7は一緒になって、無置換若しくは置換基を有する4〜8員環を形成してもよい。さらに、該4〜8員環は、環内に、式:−N(R4)−C(=O)−で表される基に結合する窒素原子以外にヘテロ原子を含んでいてもよい。 R 6 and R 7 may be combined to form a 4- to 8-membered ring having no substituent or a substituent. Further, the 4- to 8-membered ring may contain a hetero atom in addition to the nitrogen atom bonded to the group represented by the formula: —N (R 4 ) —C (═O) —.
なお、本発明化合物には、炭素−窒素二重結合に基づく、E−Zの立体異性体が存在する場合や、不斉炭素原子に基づく光学異性体が存在する場合があるが、これらの異性体はすべて本発明に含まれる。 The compound of the present invention may have an E-Z stereoisomer based on a carbon-nitrogen double bond or an optical isomer based on an asymmetric carbon atom. All bodies are included in the present invention.
(3)製造方法
化合物(I)は、例えば、以下に示す製造方法により製造することができる。
(製造方法1)
前記化合物(I)のうち、下記式(Ib)、(Ib’)で表される化合物は、下記に示す方法によって製造することができる。
(3) Manufacturing method Compound (I) can be manufactured by the manufacturing method shown below, for example.
(Manufacturing method 1)
Among the compounds (I), compounds represented by the following formulas (Ib) and (Ib ′) can be produced by the method shown below.
(式中、R1〜R3、R6、R7、及びnは前記と同じ意味を表し、A’は酸素原子又は硫黄原子を表す。)
すなわち、(i)式(1)で表されるイソ(チオ)シアネート化合物に、式(2)で表されるアミン化合物を反応させることにより、式(Ib)で表される(チオ)ウレア化合物を得ることができる。また、(ii)式(3)で表されるアミン化合物に、式(2’)で表されるイソ(チオ)シアネート化合物を反応させることにより、式(Ib’)で表される(チオ)ウレア化合物を得ることができる。これらの反応は、イソ(チオ)シアネート類とアミン類とを反応させて(チオ)ウレア化合物を得る公知の反応方法と同様にして行うことができる。
(In the formula, R 1 to R 3 , R 6 , R 7 , and n represent the same meaning as described above, and A ′ represents an oxygen atom or a sulfur atom.)
That is, (i) the (thio) urea compound represented by the formula (Ib) by reacting the iso (thio) cyanate compound represented by the formula (1) with the amine compound represented by the formula (2). Can be obtained. (Ii) By reacting an amine compound represented by formula (3) with an iso (thio) cyanate compound represented by formula (2 ′), (thio) represented by formula (Ib ′) A urea compound can be obtained. These reactions can be carried out in the same manner as in known reaction methods in which iso (thio) cyanates and amines are reacted to obtain a (thio) urea compound.
(製造方法2)
前記化合物(I)のうち、下記式(Ic)で表される化合物は、例えば、下記に示す方法によって製造することができる。
(Manufacturing method 2)
Among the compounds (I), a compound represented by the following formula (Ic) can be produced, for example, by the method shown below.
(式中、R1〜R3及びnは前記と同じ意味を表す。Lはハロゲン原子等の脱離基を表し、R5’は、無置換若しくは置換基を有するC1〜20アルキル基を表す。)
すなわち、式(3)で表されるアミン化合物と、(式(4)で表されるカルボン酸、式(5)で表される酸ハライド、又は式(6)で表される酸無水物)とを、常法により反応させて、式(Ic)で表される化合物を得ることができる。
(Wherein R 1 to R 3 and n represent the same meaning as described above, L represents a leaving group such as a halogen atom, and R 5 ′ represents an unsubstituted or substituted C 1-20 alkyl group. .)
That is, an amine compound represented by formula (3) and (carboxylic acid represented by formula (4), acid halide represented by formula (5), or acid anhydride represented by formula (6)) To obtain a compound represented by the formula (Ic).
(製造方法3)
また、下記式(Id)で表される化合物を、酸化剤を用いて酸化することにより、式(Ie)で表される化合物を得ることもできる。
(Manufacturing method 3)
Moreover, the compound represented by the formula (Ie) can also be obtained by oxidizing the compound represented by the following formula (Id) using an oxidizing agent.
(式中、R1〜R5、Aは前記と同じ意味を表し、n’は1又は2を表す。)
用いる酸化剤としては、特に制限はないが、例えば、m−クロロ過安息香酸、過酢酸等が挙げられる。
(In the formula, R 1 to R 5 and A represent the same meaning as described above, and n ′ represents 1 or 2.)
The oxidizing agent to be used is not particularly limited, and examples thereof include m-chloroperbenzoic acid and peracetic acid.
(製造方法4)
下記式で示すように、式(Id)で表される化合物に、シアナミド及びヨードベンゼンジアセタート等の酸化剤を反応させることにより、式(I)において、A=O、n=0、m=1で、X=N−CNである化合物(If)を得ることができる(Organic Letters,2007,9(15),2951等を参照)。
(Manufacturing method 4)
As shown by the following formula, by reacting the compound represented by the formula (Id) with an oxidizing agent such as cyanamide and iodobenzene diacetate, in the formula (I), A = O, n = 0, m = 1 and X = N-CN (If) can be obtained (see Organic Letters, 2007, 9 (15), 2951, etc.).
(式中、R1〜R5、Aは前記と同じ意味を表す。)
(製造方法5)
下記式で示すように、式(Id’)で表される化合物を公知の方法によりSアルキル化して、式(Ig)で表される化合物を得た後、式(Ig)で表される化合物に、式:Q’−NH2〔Q’はOR10(R10は前記と同じ意味を表す。)で表される基を示す。〕で表される化合物を反応させることによって、式(I)において、R4=H、A=NOR10、n=0、m=0である化合物(Ih)を得ることができる。
(Wherein R 1 to R 5 and A represent the same meaning as described above.)
(Manufacturing method 5)
As shown by the following formula, the compound represented by the formula (Id) is S-alkylated by a known method to obtain the compound represented by the formula (Ig), and then the compound represented by the formula (Ig). , Q′—NH 2 [Q ′ represents a group represented by OR 10 (where R 10 represents the same meaning as described above). In the formula (I), a compound (Ih) in which R 4 = H, A = NOR 10 , n = 0, and m = 0 can be obtained.
(式中、R1〜R3、R5、Q’は前記と同じ意味を表し、R11はアルキル基を表す。)
(製造方法6)
下記式で示すように、式(3’)で表される化合物に、(S,S)−ジアルキル−N−シアノジチオイミノカルボナート(7)を作用させて、式(Ii)で表される化合物を得ることができる。また、このものに、式(a’)
(In the formula, R 1 to R 3 , R 5 and Q ′ represent the same meaning as described above, and R 11 represents an alkyl group.)
(Manufacturing method 6)
As shown by the following formula, (S, S) -dialkyl-N-cyanodithioiminocarbonate (7) is allowed to act on the compound represented by the formula (3 ′) to represent the formula (Ii). A compound can be obtained. In addition, the formula (a ′)
で表される化合物をさらに反応させることによって、式(I)において、R4=H、A=NCN、n=0、m=0であり、R5が、式(a’) In the formula (I), R 4 = H, A = NCN, n = 0, m = 0, and R 5 is represented by the formula (a ′).
で表される、無置換若しくは置換基を有する含窒素ヘテロ環基である化合物(Ij)を得ることができる(下記)。 A compound (Ij) that is an unsubstituted or substituted nitrogen-containing heterocyclic group represented by formula (I) can be obtained (below).
(式中、R1〜R3は前記と同じ意味を表し、R12はアルキル基を表す。)
化合物(I)の塩としては、農園芸学的に許容されるものであれば特に限定されない。例えば、化合物(I)の、塩酸塩、硝酸塩、硫酸塩、リン酸塩等の無機酸の塩;酢酸、プロピオン酸、乳酸等の有機酸の塩;が挙げられる。
化合物(I)の塩は、例えば、化合物(I)に、無機酸又は有機酸を作用させることにより製造することができる。
(In the formula, R 1 to R 3 represent the same meaning as described above, and R 12 represents an alkyl group.)
The salt of compound (I) is not particularly limited as long as it is acceptable in agriculture and horticulture. Examples thereof include salts of inorganic acids such as hydrochlorides, nitrates, sulfates and phosphates of compounds (I); salts of organic acids such as acetic acid, propionic acid and lactic acid.
The salt of compound (I) can be produced, for example, by reacting compound (I) with an inorganic acid or an organic acid.
いずれの反応においても、反応終了後は有機合成化学における通常の後処理操作、及び分離精製を行うことにより、目的物を単離することができる。
目的物の構造は、元素分析、NMRスペクトル、IRスペクトル、マススペクトル等の公知の分析手段により同定、確認することができる。
In any reaction, after completion of the reaction, the desired product can be isolated by carrying out usual post-treatment operations in organic synthetic chemistry and separation and purification.
The structure of the target product can be identified and confirmed by known analytical means such as elemental analysis, NMR spectrum, IR spectrum, and mass spectrum.
(4)殺ダニ剤
本発明の殺ダニ剤は、以上のようにして得られる化合物(I)及びその塩(以下、「化合物(I)等」という。)の少なくとも一種を有効成分として含有する。
(4) Acaricide The acaricide of the present invention contains as an active ingredient at least one of the compound (I) obtained as described above and a salt thereof (hereinafter referred to as “compound (I) etc.”). .
本発明の殺ダニ剤中の有効成分量は、特に限定されないが、好ましくは0.01〜90重量%、特に好ましくは0.05〜85重量%である。 The amount of the active ingredient in the acaricide of the present invention is not particularly limited, but is preferably 0.01 to 90% by weight, particularly preferably 0.05 to 85% by weight.
化合物(I)等は、各種ダニ類に対して、優れた殺成虫、殺若虫、殺幼虫、殺卵作用を有する。化合物(I)等を有効成分として含有する本発明の殺ダニ剤は、農園芸作物に寄生するハダニ類を防除する農園芸用殺ダニ剤として、あるいは、衛生害虫であるマダニ類を防除する防疫用殺ダニ剤等として使用できる。
本発明の殺ダニ剤は、殺ダニ剤抵抗性系統の農園芸作物に寄生するダニにも優れた殺ダニ効果を有する。
また、本発明の殺ダニ剤は薬害が少なく、魚類や温血動物への毒性が低く、安全性の高い薬剤である。
Compound (I) and the like have excellent killing, larvicidal, larvicidal and ovicidal action against various mites. The acaricide of the present invention containing the compound (I) or the like as an active ingredient is used as an agro-horticultural acaricide for controlling spider mites parasitizing agricultural or horticultural crops or as a sanitary pest for controlling ticks. It can be used as an acaricide.
The acaricide of the present invention has an excellent acaricidal effect on mites parasitic on agricultural and horticultural crops of acaricide-resistant strains.
Further, the acaricide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
本発明の殺ダニ剤が防除の対象とするダニ類としては、例えば、ナミハダニ、ニセナミハダニ、カンザワハダニ、ミカンハダニ、リンゴハダニ、ミカンサビダニ、リンゴサビダニ、チャノホコリダニ、ブレビパルパス属、エオテトラニカス属、ロビンネダニ、ケナガコナダニ、コナヒョウヒダニ、オウシマダニ、フタトゲチマダニ等が挙げられる。 Examples of mites to be controlled by the acaricide of the present invention include, for example, urticae, spider mites, kanzawa spider mites, citrus spider mites, apple spider mites, citrus spider mites, apple rustic mites, tea dust mites, brevipalpas spp. Examples include mites and ticks.
本発明の殺ダニ剤を農園芸用殺ダニ剤として使用する場合、化合物(I)等の一種又は二種以上を、他の成分を加えることなくそのまま使用することができる。また、化合物(I)等に、さらに、各種添加剤、固体担体、液体担体、ガス状担体等を混合し、或いは、化合物(I)等を、多孔セラミック板や不織布等の基剤に含浸し、必要により界面活性剤、その他の補助剤を添加して製剤化することもできる。かかる製剤としては、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤、フロアブル、エアゾール、煙霧剤、加熱蒸散剤、燻煙剤、毒餌、マイクロカプセル等が挙げられる。 When the acaricide of the present invention is used as an agricultural and horticultural acaricide, one or more compounds (I) and the like can be used as they are without adding other components. Further, various additives, solid carrier, liquid carrier, gaseous carrier, etc. are further mixed with compound (I) or the like, or compound (I) or the like is impregnated into a base such as a porous ceramic plate or nonwoven fabric. If necessary, a surfactant and other auxiliary agents can be added to prepare a formulation. Such preparations include wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, wettable granules, flowables, aerosols, fumes, heat transpiration agents, smokers, poison baits, microcapsules and the like. It is done.
用いる添加剤及び担体としては、固体の剤型を目的とする場合は、大豆粒、小麦粉等の植物性粉末;珪藻土、燐灰石、石こう、タルク、ベントナイト、パイロフィライト、クレイ等の鉱物性微粉末;安息香酸ソーダ、尿素、芒硝等の有機及び無機化合物;が挙げられる。また、液体の剤型を目的とする場合は、ケロシン、キシレン及びソルベントナフサ等の石油留分、シクロヘキサン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、アルコール、アセトン、メチルイソブチルケトン、鉱物油、植物油、水等を溶剤として使用することができる。噴射剤を目的とする場合には、ブタンガス、LPG、ジメチルエーテル及び炭酸ガス等のガス状担体を使用することができる。 Additives and carriers used are vegetable powders such as soybean grains and wheat flour for the purpose of solid dosage forms; mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay Organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate. For liquid dosage forms, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be used as a solvent. For the purpose of a propellant, gaseous carriers such as butane gas, LPG, dimethyl ether and carbon dioxide can be used.
界面活性剤は均一かつ安定な形態をとるために添加される。用いる界面活性剤としては、特に限定されない。例えば、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテル等の非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン−無水マレイン酸の共重合体等が挙げられる。 Surfactants are added to take a uniform and stable form. The surfactant to be used is not particularly limited. For example, nonionic surfactants such as alkyl ethers added with polyoxyethylene, higher fatty acid esters added with polyoxyethylene, sorbitan higher fatty acid esters added with polyoxyethylene, and tristyryl phenyl ether added with polyoxyethylene , Sulfates of alkylphenyl ethers with addition of polyoxyethylene, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, copolymers of isobutylene-maleic anhydride Etc.
本発明の殺ダニ剤は、その製剤形態が水和剤、乳剤、懸濁剤、フロアブル剤、水溶剤、顆粒水和剤等である場合には、これらの製剤を水で所定の濃度に希釈して、溶解液、懸濁液あるいは乳濁液として使用することができる。また、粉剤・粒剤である場合には、そのまま植物或いは土壌に散布する方法で使用することができる。 The acaricide of the present invention is diluted to a predetermined concentration with water when the formulation is a wettable powder, emulsion, suspension, flowable, aqueous solvent, granular wettable powder, etc. Thus, it can be used as a solution, suspension or emulsion. Moreover, when it is a powder agent and a granule, it can be used by the method of spraying to a plant or soil as it is.
本発明の殺ダニ剤を防疫用の殺ダニ剤として使用する場合には、その製剤形態を、乳剤、水和剤、フロアブル剤とし、これらの製剤を水で所定の濃度に希釈して施用することができる。また、その製剤形態が、油剤、エアゾール、煙霧剤、毒餌、防ダニシート等である場合には、そのまま施用することができる。 When the acaricide of the present invention is used as an acaricide for epidemics, the preparation form is an emulsion, a wettable powder, and a flowable agent, and these preparations are diluted with water to a predetermined concentration and applied. be able to. Moreover, when the formulation form is an oil agent, an aerosol, an aerosol, a poison bait, an anti-tick sheet, etc., it can be applied as it is.
ウシ、ブタ等の家畜類、イヌ、ネコ等のペット類の動物外部寄生虫防除用の有害生物防除剤として使用する場合は、本発明化合物を、獣医学的に公知の方法で製剤して用いることができる。その使用方法としては、例えば全身的抑制(systemic control)を目的とする場合には、錠剤、カプセル、浸漬液、飼料混入、坐薬、注射(筋肉内、皮下、静脈内、腹腔内等)等により投与する方法が挙げられ、非全身的(non−systemic control)を目的とする場合は、油性または水性液剤を噴霧、注ぎかけ(pour−on)、滴下(spot−on)等により投与する方法および樹脂製剤を首輪、耳札等の適当な形状に成形した物を装着する方法が挙げられる。この場合、宿主動物1kgに対して、本発明化合物として、通常0.01−1000mgの割合で使用することができる。 When used as a pest control agent for controlling animal ectoparasites in domestic animals such as cattle and pigs, and pets such as dogs and cats, the compound of the present invention is formulated and used by a method known in veterinary medicine. be able to. For example, for the purpose of systemic control, tablets, capsules, immersion liquid, feed mixing, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) etc. In the case of non-systemic control, an oily or aqueous solution is administered by spraying, pouring-on, dropping-on, etc. The method of mounting | wearing the thing which shape | molded the resin formulation in appropriate shapes, such as a collar and an ear tag, is mentioned. In this case, the compound of the present invention can be usually used at a ratio of 0.01 to 1000 mg per 1 kg of the host animal.
本発明の殺ダニ剤は単独でも十分有効であることはいうまでもないが、他の殺ダニ剤、殺菌剤、殺虫・殺ダニ剤、除草剤、植物調節剤、共力剤、肥料、土壌改良剤、動物用飼料、他の衛生害虫駆除剤等の1種又は2種以上と混用又は併用することもできる。 Needless to say, the acaricide of the present invention alone is sufficiently effective, but other acaricides, fungicides, insecticides / acaricides, herbicides, plant regulators, synergists, fertilizers, soils It can also be used in combination or in combination with one or more improvers, animal feeds, other sanitary pesticides and the like.
また、必要に応じて製剤時又は散布時に他種の除草剤、各種殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土壌改良剤等と混合施用しても良い。 If necessary, mix with other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. It may be applied.
特に他の農薬あるいは植物ホルモンと混合施用することにより、施用薬量の低減による低コスト化、混合薬剤の相乗作用による殺虫スペクトラムの拡大やより高い有害生物防除効果が期待できる。この際、同時に複数の公知農薬との組み合わせも可能である。 In particular, when mixed with other pesticides or plant hormones, the cost can be reduced by reducing the amount of applied medicine, the insecticidal spectrum can be expanded by the synergistic action of the mixed drugs, and higher pest control effects can be expected. At this time, a combination with a plurality of known agricultural chemicals is also possible.
本発明化合物と混合使用する農薬の種類としては、例えばクロップ・プロテクション・ハンドブック(Crop Protection Handbook)2007年版に記載されている化合物等が挙げられる。具体的にその一般名を例示すれば次の通りであるが、必ずしもこれらのみに限定されるものではない。 Examples of the type of agricultural chemical used in combination with the compound of the present invention include compounds described in the 2007 Crop Protection Handbook 2007 edition. Specific examples of common names are as follows, but the general names are not necessarily limited to these.
殺菌剤の有効成分化合物(一般名;一部申請中を含む)としては、例えば、メパニピリム(mepanipyrim)、ピリメタニル(pyrimethanil)、シプロジニル(cyprodinil)等のアニリノピリミジン系化合物;
フルアジナム(fluazinam)等のピリジナミン系化合物;
トリアジメホン(triadimefon)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、マイクロブタニル(myclobutanil)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、ファーコナゾールシス(furconazole‐cis)、プロクロラズ(prochloraz)、メトコナゾール(metconazole)、エポキシコナゾール(epoxiconazole)、テトラコナゾール(tetraconazole)、オキスポコナゾールフマル酸塩(oxpoconazole fumarate)、シプコナゾール(sipconazole)、プロチオコナゾール(prothioconazole)、トリアジメノール(triadimenol)、フルトリアフオール(flutriafol)、ジフェノコナゾール(difenoconazole)、フルキンコナゾール(fluquinconazole)、フェンブコナゾール(fenbuconazole)、ブロムコナゾール(bromuconazole)、ジニコナゾール(diniconazole)、トリシクラゾール(tricyclazole)、プロベナゾール(probenazole)、シメコナゾール(simeconazole)、ペフラゾエート(pefurazoate)、イプコナゾール(ipconazole)、イミベンコナゾール(imibenconazole)、イマザリル(imazalil)等のアゾール系化合物;
As an active ingredient compound (generic name; including some applications) of fungicides, for example, ananilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc .;
Pyridinamine compounds such as fluazinam;
Triadimefone, bittertanol, triflumizole, etaconazole, propiconazole, penconazole, luconilole, flusilazole, penconazole, flusilazole. cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole ), Tetraconazole, oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol (triadimenol), triadimenol (triadimenol) difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, tricyclazole meconazole), pefurazoate (pefurazoate), ipconazole (ipconazole), imibenconazole (imibenconazole), azole compounds such as imazalil (imazalil);
キノメチオネート(quinomethionate)のようなキノキサリン系化合物;
マンネブ(maneb)、ジネブ(zineb)、マンゼブ(mancozeb)、ポリカーバメート(polycarbamate)、メチラム(metiram)、プロピネブ(propineb)、フェバム(ferbam)、ナーバム(nabam)、メタム(metam)、チラム(thiram)、ジラム(ziram)等のジチオカーバメート系化合物;
Quinoxaline-based compounds such as quinomethionate;
Manneb, zineb, manzeb, polycarbamate, metyram, propineb, febam, nabam, m, la , Dithiocarbamate compounds such as ziram;
フサライド(fthalide)、クロロタロニル(chlorothalonil)、キントゼン(quintozene)等の有機塩素系化合物;
ベノミル(benomyl)、チオファネートメチル(thiophanate‐methyl)、カルベンダジム(carbendazim)、チアベンダゾール(thiabendazole)、フベリアゾール(fuberiazole)、シアゾファミド(cyazofamid)等のイミダゾール系化合物;
シモキサニル(cymoxanil)等のシアノアセトアミド系化合物;
メタラキシル(metalaxyl)、メタラキシル−M(metalaxyl−M)、メフェノキサム(mefenoxam)、オキサジキシル(oxadixyl)、オフレース(ofurace)、ベナラキシル(benalaxyl)、ベナラキシル−M(benalaxyl−M)、フララキシル(furalaxyl)、シプロフラム(cyprofuram)等のフェニルアミド系化合物;
ジクロフルアニド(dichlofluanid)のようなスルフェン酸系化合物;
ジノキャップ(dinocap)等のニトロフェニル系化合物;
水酸化第二銅(cupric hydroxide)、有機銅(oxine copper)等の銅系化合物;
ヒメキサゾール(hymexazol)等のイソキサゾール系化合物;
ホセチルアルミニウム(fosetyl−Al)、トルコホスメチル(tolcofos‐methyl)、S−ベンジル O,O−ジイソプロピルホスホロチオエート、O−エチル S,S−ジフェニルホスホロジチオエート、アルミニウムエチルハイドロゲンホスホネート等の有機リン系化合物;
Organochlorine compounds such as fthalide, chlorothalonil, quintozen;
Imidol compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberizole, cyazofamide, etc .;
Cyanoacetamide-based compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, metalphenyl, mefenoxam, oxadixyl, offlace, benalaxyl, furaxyl-M (x) Phenylamide compounds such as (cyprofuram);
Sulfenic acid-based compounds such as dichlorfluanid;
Nitrophenyl compounds such as dinocap;
Copper-based compounds such as cupric hydroxide and organic copper;
Isoxazole-based compounds such as hymexazole;
Organophosphorus compounds such as fosetyl aluminum (fosetyl-Al), turkey phosmethyl (tolcofos-methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate ;
キャプタン(captan)、キャプタホル(captafol)、フォルペット(folpet)等のN−ハロゲノチオアルキル系化合物;
プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinclozolin)等のジカルボキシイミド系化合物;
フルトラニル(flutolanil)、メプロニル(mepronil)、ゾキサミド(zoxamid)、チアジニル(tiadinil)等のベンズアニリド系化合物;
カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ペンチオピラド(penthiopyrad)、ボスカリド(boscalid)、フルオピコリド(fluopicolide)、フルオピラム(fluopyram)、ビキサフェン(bixafen)等のアニリド系化合物;
N-halogenoalkyl compounds such as captan, captafol, folpet, etc .;
Dicarboximide compounds such as procymidone, iprodione, and vinclozolin;
Benzanilide compounds such as flutolanil, mepronil, zoxamide, thiadinyl;
Carboxin, oxycarboxin, thifluzamide, pentiopyrad, boscalid, fluopicolide, fluopyramide, fluopyram
トリホリン(triforine)等のピペラジン系化合物;
ピリフェノックス(pyrifenox)等のピリジン系化合物;
フェナリモル(fenarimol)、フルトリアフォル(flutriafol)等のカルビノール系化合物;
フェンプロピディン(fenpropidine)等のピペリジン系化合物;
フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph)等のモルフォリン系化合物;
フェンチンヒドロキシド(fentin hydroxide)、フェンチンアセテート(fentin acetate)等の有機スズ系化合物;
ペンシキュロン(pencycuron)等の尿素系化合物;
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)フルメトーバー(flumetover)等のシンナミック酸系化合物;
ジエトフェンカルブ(diethofencarb)等のフェニルカーバメート系化合物;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol, flutriafol;
Piperidine-based compounds such as fenpropidine;
Morpholine compounds such as fenpropimorph and tridemorph;
Organotin compounds such as fentin hydroxide and fentin acetate;
Urea compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph and flumetober;
Phenyl carbamate compounds such as dietofencarb;
フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)等のシアノピロール系化合物;
アゾキシストロビン(azoxystrobin)、クレソキシムメチル(kresoxim‐methyl)、メトミノフェン(metominofen)、メトミノストロビン(metominostrobin)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、オリザストロビン(oryzastrobin)、ジモキシストロビン(dimoxystrobin)、ピラクロストロビン(pyraclostrobin)、フルオキサストロビン(fluoxastrobin)等のストロビルリン系化合物;
ファモキサドン(famoxadone)等のオキサゾリジノン系化合物;
エタボキサム(ethaboxam)等のチアゾールカルボキサミド系化合物;
シルチオファム(silthiopham)等のシリルアミド系化合物;
イプロバリカルブ(iprovalicarb)、ベンチアバリカルブ−イソプロピル(benthiavalicarb−isopropyl)等のアミノアシッドアミドカーバメート系化合物;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, cresoxime-methyl, methminophen, methminostrobin, trifloxystrobin, picoxystrobin, picoxyzine Strobilurin-based compounds such as dimoxystrobin, pyraclostrobin, fluoxastrobin, etc .;
Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as silthiopham;
Amino acid amide carbamate compounds such as iprovalicalcarb, benchavaricarb-isopropyl;
フェナミドン(fenamidone)等のイミダゾリジン系化合物;
フェンヘキサミド(fenhexamid)等のハイドロキシアニリド系化合物;
フルスルファミド(flusulfamide)等のベンゼンスルホンアミド系化合物;
シフルフェナミド(cyflufenamid)等のオキシムエーテル系化合物;
フェノキサニル(fenoxanil)等のフェノキシアミド系化合物;
バリダマイシン(validamycin)、カスガマイシン(kasugamycin)、ポリオキシン(polyoxins)等の抗生物質;
イミノクタジン(iminoctadine)等のグアニジン系化合物;
Imidazolidine compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamide;
Benzenesulfonamide-based compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamide;
Phenoxyamide compounds such as phenoxanil;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadin;
また、その他の化合物として、トリフルアニド(tolyfluanid)、イソプロチオラン(isoprothiolane)、ピロキロン(pyroquilon)、ジクロメジン(diclomezine)、キノキシフェン(quinoxyfen)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、スピロキサミン(spiroxamine)、クロルピクリン(chloropicrin)、ダゾメット(dazomet)、メタムナトリウム塩(metam‐sodium)、ニコビフェン(nicobifen)、メトラフェノン(metrafenone)、UBF−307、ジクロシメット(diclocymet)、プロキンアジド(proquinazid)、アミスルブロム(amisulbrom)、ピリベンカルブ(pyribencarb)、マンジプロパミド(mandipropamid)、5−chlor−7−(4−methyl−piperidin−1−yl)−6−(2,4,6−trifluor−phenyl)−[1,2,4]triazolo[1,5−a]pyrimidin、OK−5203等が挙げられる。 Other compounds include trifluanid, isoprothiolane, pyroquilon, diclomezine, quinoxyspirin, propamocarbine hydrochloride. Dazomet, metham-sodium, nicobifen, metraphenone, UBF-307, diclocymet, proquinazide, amisulbrom amisulbrom, pyribencarb, mandipropamide, 5-chlor-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluor-phenyl)-[1,2, 4] triazolo [1,5-a] pyrimidin, OK-5203, and the like.
散布液中の農薬類である、殺虫剤、殺ダニ剤、殺線虫剤或いは殺土壌害虫剤の有効成分化合物(一般名;一部申請中を含む)としては、例えば、プロフェノホス(profenofos)、ジクロルボス(dichlorvos)、フェナミホス(fenamiphos)、フェニトロチオン(fenitrothion)、EPN、ダイアジノン(diazinon)、クロルピリホスメチル(chlorpyrifos−methyl)、アセフェート(acephate)、プロチオホス(prothiofos)、ホスチアゼート(fosthiazate)、ホスホカルブ(phosphocarb)、カズサホス(cadusafos)、ジスルホトン(dislufoton)、クロルピリホス(chlorpyrifos)、デメトン−S−メチル(demeton−S−methyl)、ジメトエート(dimethoate)、メタミドホス(methamidophos)、イソキサチオン(isoxathion)、イソフェンホス(isofenphos)、エチオン(ethion)、エトリムホス(etrimfos)、キナルホス(quinalphos)、ジメチルビンホス(dimethylvinphos)、スルプロホス(sulprofos)、チオメトン(thiometon)、バミドチオン(vamidothion)、ピラクロホス(pyraclofos)、ピリダフェンチオン(pyridaphenthion)、ピリミホスメチル(pirimiphos−methyl)、プロパホス(propaphos)、ホサロン(phosalone)、ホルモチオン(formothion)、マラチオン(malathion)、テトラクロルビンホス(tetrachlovinphos)、クロルフェンビンホス(chlorfenvinphos)、シアノホス(cyanophos)、トリクロルホン(trichlorfon)、メチダチオン(methidathion)、フェントエート(phenthoate)、ESP、アジンホスメチル(azinphos−methyl)、フェンチオン(fenthion)、ヘプテノホス(heptenophos)、メトキシクロル(methoxychlor)、パラチオン(paration)、モノクロトホス(monocrotophos)、イミシアホス(imicyafos)、パラチオン−メチル(parathion−methyl)、テルブホス(terbufos)、ホスファミドン(phospamidon)、ホスメット(phosmet)、ホレート(phorate)等の有機リン酸エステル系化合物; As an active ingredient compound (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil pesticides that are pesticides in the spray solution, for example, profenofos, Dichlorvos, fenamifos, fenitrothion, EPN, diazinon, chlorpyrifos-methyl, acephate, prothiophos, prothiophos, prothiophos Cadusafos, disulfoton, chlorpyrifos Demethon-S-methyl, dimethoate, methamidophos, isoxathion, isofenphos, etionfos, dimethylfos, quinolphos Phosphite (dimethylvinphos), sulprofos, thiomethon, bamidithion, pyraclofos, pyridafenthion, pirimiphosmethyl, Phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorthone, methithion, methithion , ESP, azinephos-methyl, fenthion, heptenophos, methoxychlor, parathion, monocrotophos, imiciafos, imiparafos Organophosphate compounds such as thione-methyl, terbufos, phosphamidon, phosmet, and phosphate;
カルバリル(carbaryl)、プロポキスル(propoxur)、アルジカルブ(aldicarb)、カルボフラン(carbofuran)、チオジカルブ(thiodicarb)、メソミル(methomyl)、オキサミル(oxamyl)、エチオフェンカルブ(ethiofencarb)、ピリミカルブ(pirimicarb)、フェノブカルブ(fenobucarb)、カルボスルファン(carbosulfan)、ベンフラカルブ(benfuracarb)、ベンジオカルブ(bendiocarb)、フラチオカルブ(furathiocab)、イソプロカルブ(isoprocarb)、メトルカルブ(metolcarb)、キシリルカルブ(xylylcarb)、XMC、フェノチオカルブ(fenothiocarb)等のカーバメート系化合物; Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, thiomil, ethiophencarb Carbosulfan, benfuracarb, bendiocarb, furatiocarb, isoprocarb, metocarb, xylylcarb, xylylcarb, xylylcarb Fenothiocarb) carbamate compounds such as;
カルタップ(cartap)、チオシクラム(thiocyclam)、ベンスルタップ(bensultap)、チオスルタップナトリウム(thiosultap−sodium)等のネライストキシン誘導体;
ジコホル(dicofol)、テトラジホン(tetradifon)、エンドスルファン(endosulufan)、ジエノクロル(dienochlor)、ディルドリン(dieldrin)のような有機塩素系化合物;
酸化フェンブタスズ(fenbutatin oxide)、シヘキサチン(cyhexatin)等の有機金属系化合物;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicophor, tetradiphon, endosulfan, dienochlor, dieldrin;
Organometallic compounds such as fenbutatin oxide and cyhexatin;
フェンバレレート(fenvalerate)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、デルタメトリン(deltamethrin)、シハロトリン(cyhalothrin)、テフルトリン(tefluthrin)、エトフェンプロックス(ethofenprox)、シフルトリン(cyfluthrin)、フェンプロパトリン(fenpropathrin)、ビフェントリン(bifenthrin)、フルシトリネート(flucythrinate)、フルバリネート(fluvalinate)、シクロプロトリン(cycloprothrin)、ラムダシハロトリン(lambda−cyhalothrin)、ピレスリン(pyrethrins)、エスフェンバレレート(esfenvalerate)、テトラメスリン(tetramethrin)、レスメスリン(resmethrin)、プロトリフェンブト(protrifenbute)、ゼータシペルメトリン(zeta−cypermethrin)、アクリナトリン(acrinathrin)、アルファシペルメトリン(alpha−cypermethrin)、アレスリン(allethrin)、ガンマシハロトリン(gamma−cyhalothrin)、シータシペルメトリン(theta−cypermethrin)、タウフルバリネート(tau−fluvalinate)、トラロメスリン(tralomethrin)、プロフルスリン(profluthrin)、ベータシペルメトリン(beta−cypermethrin)、 ベータシフルトリン(beta−cyfluthrin)、メトフルトリン(metofluthrin)、フェノトリン(phenothrin)等のピレスロイド系化合物; Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprothrin , Bifenthrin, flucitrinate, fluvalinate, cycloprotorin, lambda-cyhalothrin, pyrethrins, esphethrins. Valenate (esfenvalerate), tetramethrin (resmethrin), protrifenbute (zetriperperthrin), acrinathrin (alpha) permethrin, alpha cyperthrin (alpha) permethrin , Gamma-cyhalothrin, theta-permethrin, tau-fluvalinate, tralomethrin, profluthrin, beta-cypermethrin cypermethrin), beta-cyfluthrin (beta-cyfluthrin), metofluthrin (metofluthrin), pyrethroid compounds such as phenothrin (phenothrin);
ジフルベンズロン(diflubenzuron)、クロルフルアズロン(chlorfluazuron)、テフルベンズロン(teflubenzuron)、フルフェノクスロン(flufenoxuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、トリフルムロン(triflumuron)、ヘキサフルムロン(hexaflumuron)、ノビフルムロン(noviflumuron)、ビストリフルロン(bistrifluron)、フルアズロン(fluazuron)等のベンゾイルウレア系化合物;
メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、フェノキシカルブ(fenoxycarb)、ジオフェノラン(diofenolan)等の幼若ホルモン様化合物;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, flufenuron, flufluonzuron, flufluonzuron, flufluonzuron ), Bistrifluron, benzoylurea compounds such as fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, phenoxycarb, diofenolan;
ピリダベン(pyridaben)等のピリダジノン系化合物;
フェンピロキシメート(fenpyroximate)、フィプロニル(fipronil)、テブフェンピラド(tebufenpyrad)、エチプロール(ethiprole)、トルフェンピラド(tolfenpyrad)、アセトプロール(acetoprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)のようなピラゾール系化合物;
イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、クロチアニジン(clothianidin)、ジノテフラン(dinotefuran)、ニチアジン(nithiazine)等のネオニコチノイド;
テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)等のヒドラジン系化合物;
Pyridazinone compounds such as pyridaben;
Fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, acetoprole, pyrafluprol
Imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, crothianidin, intefuridin, intefuridin
Hydrazine compounds such as tebufenozide, methoxyphenozide, chromafenozide, halofenozide;
その他の化合物として、フロニカミド(flonicamid)、ブプロフェジン(buprofezin)、ヘキシチアゾクス(hexythiazox)、 アミトラズ(amitraz)、クロルジメホルム(chlordimeform)、シラフルオフェン(silafluofen)、トリアザメイト(triazamate)、ピメトロジン(pymetrozine)、ピリミジフェン(pyrimidifen)、クロルフェナピル(chlorfenapyr)、インドキサカルブ(indoxacarb)、アセキノシル(acequinocyl)、エトキサゾール(etoxazole)、シロマジン(cyromazine)、1,3−ジクロロプロペン(1,3−dichloropropene)、ジアフェンチウロン(diafenthiuron)、ベンクロチアズ(benclothiaz)、フルフェンリム(flufenerim)、ピリダリル(pyridalyl)、スピロジクロフェン(spirodiclofen)、ビフェナゼート(bifenazate)、スピロメシフェン(spiromesifen)、スピロテトラマット(spirotetramat)、プロパルギット(propargite)、クロフェンテジン(clofentezine)、フルアクリピリム(fluacrypyrim)、メタフルミゾン(metaflumizone)、フルベンジアミド(flubendiamide)、シフルメトフェン(cyflumetofen)、クロルアントラニルピロール(chlorantraniliprole)、シエノピラフェン(cyenopyrafen)、ピリフルキナゾン(pyrifluquinazon)、フェナザキン(fenazaquin)、アミドフルメット(amidoflumet)、クロロベンゾエート(chlorobenzoate)、スルフルアミド(sulfluramid)、ヒドラメチルノン(hydramethylnon)、メタアルデヒド(metaldehyde)、リアノジン(ryanodine)等の化合物等が挙げられる。 Other compounds include flonicamid, buprofezin, hexythiazox, imitraz, chlordiform, siroflumine, ziramifene, zilaziofene, zilaziofene, zilaziofene, Chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene, 1,3-dichloropropene Dithiophenon, benclothiaz, flufenrim, pyridalyl, spirodiclofen, bifenatroet, spiromestrofen, spiromethifen , Clofentezine, fluacrylpyrim, metaflumizone, flubenamide, cyflumethofen, chloranthranylpyrrole (chlorantra) iliprole, cienopyrafen, pyrifluquinazone, phenazaquin, amidoflumet, etholydine, chlorobenzoate (chlorophenoate) and compounds such as ryanodine).
更に、Bacillus thuringienses aizawai、Bacillus thuringienses kurstaki、Bacillus thuringienses israelensis、Bacillus thuringienses japonensis、Bacillus thuringienses tenebrionis、Bacillus thuringiensesが生成する結晶タンパク毒素、昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤等のような微生物農薬、アベルメクチン(avermectin)、エマメクチンベンゾエート(emamectin−benzoate)、ミルベメクチン(milbemectin)、スピノサッド(spinosad)、イベルメクチン(ivermectin)、レピメクチン(lepimectin)、等のような抗生物質或いは半合成抗生物質;
アザディラクチン(azadirachtin)、ロテノン(rotenone)等のような天然物;
ピペロニルブトキシド(piperonyl butoxide)のような協力剤;
ディート(deet)のような忌避剤等が挙げられる。
Furthermore, Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis, crystal protein toxin Bacillus Thuringienses generated, entomopathogenic viral agents, entomopathogenic fungus agent, nematode pathogenic fungi agent Microbial pesticides, avermectin, emamectin-benzoate, milbemectin, spinosad, ivermec Down (ivermectin), lepimectin (lepimectin), antibiotics or semisynthetic antibiotics such as and the like;
Natural products such as azadirachtin, rotenone, etc .;
Synergists such as piperonyl butoxide;
Examples include repellents such as deet.
次に、実施例を挙げて、本発明をさらに詳細に説明するが、以下の実施例によって本発明は何ら制限されることはない。なお、化合物番号は、下記第2表〜第4表中の化合物番号に対応する。 EXAMPLES Next, although an Example is given and this invention is demonstrated further in detail, this invention is not restrict | limited at all by the following examples. The compound numbers correspond to the compound numbers in Tables 2 to 4 below.
(実施例1)
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキサミドの合成
Example 1
Synthesis of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxamide
2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン0.5gを酢酸エチル15mlに溶解し、ビス(トリクロロメチル)カーボネート0.25gを加え3時間加熱還流した。得られた反応混合物を減圧濃縮し、2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)イソシアネート0.55gを得た。2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)イソシアネートにベンゼン15mlを加え、水冷下で3,3,4,4−テトラフルオロピロリジン塩酸塩0.41gとN−エチルジイソプロピルアミン0.54gを添加し、室温で6時間撹拌した。反応混合物に水冷下で1規定塩酸を加えて分液して、有機層を分取した。有機層を飽和食塩水で洗浄し無水硫酸マグネシウムで乾燥した。溶媒を減圧留去して粗生成物を得た。粗生成物をジエチルエーテルとn−ヘキサン混合溶媒で洗浄して、3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキサミド(化合物番号6)0.51gを白色結晶として得た。(融点135−137℃) 0.5 g of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline was dissolved in 15 ml of ethyl acetate, 0.25 g of bis (trichloromethyl) carbonate was added, and the mixture was heated to reflux for 3 hours. . The obtained reaction mixture was concentrated under reduced pressure to obtain 0.55 g of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) isocyanate. 15 ml of benzene is added to 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) isocyanate, and 0.41 g of 3,3,4,4-tetrafluoropyrrolidine hydrochloride and N are added under water cooling. -0.54g of ethyl diisopropylamine was added, and it stirred at room temperature for 6 hours. 1N Hydrochloric acid was added to the reaction mixture under water cooling to separate it, and the organic layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with a mixed solvent of diethyl ether and n-hexane to give 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoro). Ethylthio) phenyl] pyrrolidine-1-carboxamide (Compound No. 6) 0.51 g was obtained as white crystals. (Melting point 135-137 ° C)
(実施例2)
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルスルフィニル)フェニル〕ピロリジン−1−カルボキサミドの合成
(Example 2)
Synthesis of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] pyrrolidine-1-carboxamide
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキサミド0.30gをクロロホルム20mlに溶解し、氷水冷下で3−クロロ過安息香酸0.22gを加え室温で3時間撹拌した。反応混合物に炭酸水素ナトリウム水溶液を加え分液後、有機層を水洗し無水硫酸マグネシウムで乾燥した。溶媒を減圧留去して粗生成物を得た。粗生成物をシリカゲルカラムクロマトグラフィーで精製して(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)、3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルスルフィニル)フェニル〕ピロリジン−1−カルボキサミド(化合物番号7)0.22gを白色結晶として得た。(融点61−63℃) 0.30 g of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxamide was added to 20 ml of chloroform. This was dissolved, 0.22 g of 3-chloroperbenzoic acid was added under ice-water cooling, and the mixture was stirred at room temperature for 3 hours. An aqueous sodium hydrogen carbonate solution was added to the reaction mixture for liquid separation, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate), and 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl- 0.22 g of 5- (2,2,2-trifluoroethylsulfinyl) phenyl] pyrrolidine-1-carboxamide (Compound No. 7) was obtained as white crystals. (Melting point 61-63 ° C)
(実施例3)
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N−メチルピロリジン−1−カルボキサミドの合成
(Example 3)
Synthesis of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N-methylpyrrolidine-1-carboxamide
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキサミド0.20gをN,N−ジメチルホルムアミド10mlに溶解し、氷水冷下で水素化ナトリウム30mgを加え、室温で10分間撹拌した。更に氷水冷下でヨウ化メチル0.16gを添加し、室温で4時間撹拌した。反応混合物を希塩酸中に注加し、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、溶媒を減圧留去して粗生成物を得た。得られた粗生成物をシリカゲルカラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製して、3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルスルフィニル)フェニル〕−N−メチルピロリジン−1−カルボキサミド(化合物番号9)0.17gを白色結晶として得た。(融点91−93℃) 0.24 g of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxamide was added to N, N -It melt | dissolved in 10 ml of dimethylformamide, 30 mg of sodium hydrides were added under ice water cooling, and it stirred at room temperature for 10 minutes. Furthermore, 0.16 g of methyl iodide was added under ice water cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate) to obtain 3,3,4,4-tetrafluoro-N- [2-fluoro-4. 0.17 g of -methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -N-methylpyrrolidine-1-carboxamide (Compound No. 9) was obtained as white crystals. (Melting point 91-93 ° C)
(実施例4)
N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕シクロプロパンカルボキサミドの合成
Example 4
Synthesis of N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] cyclopropanecarboxamide
2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン0.36gをジクロロメタン5mlに溶解し、シクロプロパンカルボニルクロリド0.17gとトリエチルアミン0.18gを加え1時間撹拌した。得られた反応混合物を減圧濃縮して粗生成物を得た。粗生成物をシリカゲルカラムクロマトグラフィーで精製して(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)、N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕シクロプロパンカルボキサミド(化合物番号63)0.46gを白色結晶として得た。(融点110−112℃) Dissolve 0.36 g of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline in 5 ml of dichloromethane, add 0.17 g of cyclopropanecarbonyl chloride and 0.18 g of triethylamine, and stir for 1 hour. did. The obtained reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate) and N- [2-fluoro-4-methyl-5- (2,2,2-trifluoro). Ethylthio) phenyl] cyclopropanecarboxamide (Compound No. 63) (0.46 g) was obtained as white crystals. (Melting point 110-112 ° C)
(実施例5)
S−〔4−フルオロ−2−メチル−5−(3,3,4,4−テトラフルオロピロリジン−1−カルボニルアミノ)フェニル〕−S−(2,2,2−トリフルオロエチル)−N−シアノスルフィルイミンの合成
(Example 5)
S- [4-Fluoro-2-methyl-5- (3,3,4,4-tetrafluoropyrrolidine-1-carbonylamino) phenyl] -S- (2,2,2-trifluoroethyl) -N- Synthesis of cyanosulfilimine
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキサミド0.40gをアセトニトリル5mlに溶解し、シアナミド0.05gとヨードベンゼンジアセタート0.42gを加え3時間撹拌した。得られた反応混合物を減圧濃縮して粗生成物を得た。粗生成物をシリカゲルカラムクロマトグラフィーで精製して(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)、S−〔4−フルオロ−2−メチル−5−(3,3,4,4−テトラフルオロピロリジン−1−カルボニルアミノ)フェニル〕−S−(2,2,2−トリフルオロエチル)−N−シアノスルフィルイミン(化合物番号159)0.14gを白色結晶として得た。(融点98−102℃) 0.40 g of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxamide was added to 5 ml of acetonitrile. After dissolution, 0.05 g of cyanamide and 0.42 g of iodobenzene diacetate were added and stirred for 3 hours. The obtained reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate), and S- [4-fluoro-2-methyl-5- (3,3,4,4- 0.14 g of tetrafluoropyrrolidine-1-carbonylamino) phenyl] -S- (2,2,2-trifluoroethyl) -N-cyanosulfilimine (Compound No. 159) was obtained as white crystals. (Melting point 98-102 ° C)
(実施例6)
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボチオアミドの合成
(Example 6)
Synthesis of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbothioamide
2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン 1.20gを酢酸エチル10mlに溶解した溶液に、トリエチルアミン1.0gを加えた後、さらにチオホスゲン0.57gを加え、全容を15分間攪拌した。得られた反応混合物に、3,3,4,4−テトラフルオロピロリジン塩酸塩0.99g、及びジイソプロピルエチルアミン1.9gを添加して、40℃で2時間撹拌した。反応混合物を濃縮後、濃縮物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で生成して、3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボチオアミド(化合物番号238)を1.69g得た。融点91−94℃ 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline 1.0 g of triethylamine was added to a solution of 1.20 g in 10 ml of ethyl acetate, and then 0.57 g of thiophosgene. And the whole was stirred for 15 minutes. To the obtained reaction mixture, 3,4 g of 3,3,4,4-tetrafluoropyrrolidine hydrochloride and 1.9 g of diisopropylethylamine were added and stirred at 40 ° C. for 2 hours. After the reaction mixture is concentrated, the concentrate is produced by medium pressure column chromatography (developing solvent: a mixed solvent of n-hexane and ethyl acetate), and 3,3,4,4-tetrafluoro-N- [2- 1.69 g of fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbothioamide (Compound No. 238) was obtained. Melting point 91-94 ° C
(実施例7)
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N’−ヒドロキシピロリジン−1−カルボキシイミダミドの合成
(1)メチル 3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルビミドチオエートの合成
(Example 7)
3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N'-hydroxypyrrolidine-1-carboxyimidamide (1) Methyl 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbimide Synthesis of thioate
3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボチオアミド0.8gをアセトニトリル5mlに溶解し、炭酸カリウム0.35gとヨウ化メチル0.33gを加え、室温で1昼夜撹拌した。得られた反応混合物を濃縮後、濃縮物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製して、メチル 3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルビミドチオエートをオイルとして0.73g得た。 3,0.84 g of 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbothioamide in 5 ml of acetonitrile The solution was dissolved in 0.35 g of potassium carbonate and 0.33 g of methyl iodide, and stirred at room temperature for one day. After concentrating the obtained reaction mixture, the concentrate was purified by medium pressure column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate) to obtain methyl 3,3,4,4-tetrafluoro-N. 0.73 g of-[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbimidothioate was obtained as an oil.
(2)3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N’−ヒドロキシピロリジン−1−カルボキシイミダミドの合成 (2) 3,3,4,4-Tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N′-hydroxypyrrolidine-1- Synthesis of carboxyimidamide
(1)で得た、メチル 3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルビミドチオエート0.22gをエタノール2.5mlに溶解し、ヒドロキシルアミン塩酸塩52mg及びピリジン68mgを加えた後、60℃で7時間撹拌した。得られた反応混合物を濃縮し、濃縮物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製して、(E)−3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N’−ヒドロキシピロリジン−1−カルボキシイミダミドを0.04g(化合物番号248、アモルファス)、及び、(Z)−3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N’−ヒドロキシピロリジン−1−カルボキシイミダミド(化合物番号249、融点80−81℃)を0.08gそれぞれ得た。 Methyl 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1- obtained in (1) Carbimide thioate (0.22 g) was dissolved in ethanol (2.5 ml), hydroxylamine hydrochloride (52 mg) and pyridine (68 mg) were added, and the mixture was stirred at 60 ° C. for 7 hours. The obtained reaction mixture was concentrated, and the concentrate was purified by medium pressure column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate) to obtain (E) -3,3,4,4-tetra. 0.04 g of fluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N′-hydroxypyrrolidine-1-carboxyimidamide (Compound No. 248, Amorphous) and (Z) -3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N ′ 0.08 g of -hydroxypyrrolidine-1-carboxyimidamide (Compound No. 249, melting point 80-81 ° C.) was obtained.
(実施例8)
3,3,4,4−テトラフルオロ−N−(2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル)−N’−メトキシピロリジン−1−カルボキシイミダミドの合成
(Example 8)
3,3,4,4-tetrafluoro-N- (2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl) -N'-methoxypyrrolidine-1-carboxyimidamide Synthesis of
メチル 3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルビミドチオエート0.22gをエタノール1.5mlに溶解し、メトキシアミン塩酸塩63mg及びピリジン120mgを加えた後、60℃で7時間撹拌した。反応混合物を濃縮後、濃縮物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製することで、3,3,4,4−テトラフルオロ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕−N’−メトキシピロリジン−1−カルボキシイミダミド(化合物番号260、アモルファス)を0.11g得た。 Methyl 3,3,4,4-tetrafluoro-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carbimidothioate 0.22 g Was dissolved in 1.5 ml of ethanol, 63 mg of methoxyamine hydrochloride and 120 mg of pyridine were added, and the mixture was stirred at 60 ° C. for 7 hours. After concentrating the reaction mixture, the concentrate is purified by medium pressure column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate), whereby 3,3,4,4-tetrafluoro-N- [2 0.11 g of -fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -N′-methoxypyrrolidine-1-carboxyimidamide (Compound No. 260, amorphous) was obtained.
(実施例9)
メチル N’−シアノ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕カルバミドチオエートの合成
Example 9
Synthesis of methyl N′-cyano-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] carbamidothioate
2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)アニリン 1.20gをピリジン7.5mlに溶解し、(S,S)−ジメチル−N−シアノジチオイミノカルボナート1.46gを加えた後、1昼夜加熱還流した。反応混合物に酢酸エチルと希塩酸を加え分液後、有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去して粗生成物を得た。粗生成物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製して、N’−シアノ−N−(2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル)カルバミドチオエート(化合物番号251、融点134−137℃)を0.92g得た。 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline 1.20 g is dissolved in 7.5 ml of pyridine, and (S, S) -dimethyl-N-cyanodithioiminocarbonate is dissolved. After 1.46 g was added, the mixture was heated to reflux for one day. Ethyl acetate and dilute hydrochloric acid were added to the reaction mixture and the layers were separated, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by medium pressure column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate), and N′-cyano-N- (2-fluoro-4-methyl-5- (2, 0.92 g of 2,2-trifluoroethylthio) phenyl) carbamidothioate (Compound No. 251, melting point 134-137 ° C.) was obtained.
(実施例10)
N’−シアノ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキシイミダミドの合成
(Example 10)
Synthesis of N′-cyano-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxyimidamide
メチル N’−シアノ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕カルバミドチオエート0.34gをアセトニトリル3mlに溶解し、ピロリジン0.17gを加え、60℃で10時間撹拌した。得られた反応混合物を濃縮した後、濃縮物を中圧カラムクロマトグラフィー(展開溶媒:n−ヘキサンと酢酸エチルとの混合溶媒)で精製して、N’−シアノ−N−〔2−フルオロ−4−メチル−5−(2,2,2−トリフルオロエチルチオ)フェニル〕ピロリジン−1−カルボキシイミダミド(化合物番号252、融点132−133℃)を0.27g得た。 Methyl N′-cyano-N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] carbamidothioate (0.34 g) was dissolved in 3 ml of acetonitrile, and 0.17 g of pyrrolidine was dissolved. And stirred at 60 ° C. for 10 hours. After concentrating the obtained reaction mixture, the concentrate was purified by medium pressure column chromatography (developing solvent: mixed solvent of n-hexane and ethyl acetate), and N′-cyano-N- [2-fluoro- 0.27 g of 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] pyrrolidine-1-carboxyimidamide (Compound No. 252, melting point 132-133 ° C.) was obtained.
実施例1〜10と同様にして得られる、本発明の殺ダニ剤の有効成分として用いられる化合物の構造式及び物理恒数を、実施例1〜10で得られた化合物を含め、第2表〜第4表に示す。
表中、Meはメチル基を、Etはエチル基を、Phはフェニル基を、cPrはシクロプロピル基を、cPenはシクロペンチル基を、Acはアセチル基を、Buはブチル基を、Bnはベンジル基をそれぞれ表す。なお、表中、*は結合位置を表し、[ ]は融点(℃)を示す。
Table 2 shows the structural formulas and physical constants of the compounds used as active ingredients of the acaricide of the present invention obtained in the same manner as in Examples 1 to 10, including the compounds obtained in Examples 1 to 10. To Table 4.
In the table, Me is a methyl group, Et is an ethyl group, Ph is a phenyl group, cPr is a cyclopropyl group, cPen is a cyclopentyl group, Ac is an acetyl group, Bu is a butyl group, and Bn is a benzyl group. Respectively. In the table, * represents a bonding position, and [] represents a melting point (° C.).
上記表中、*1:化合物番号248はE体であり、*2:化合物番号249はZ体である。
次に、1H−NMRスペクトルデータを示す。以下において、「s」はシングレット、「d」はダブレット、「t」はトリプレット、「br」はブロードシングレット、「q」はカルテット、「m」はマルチプレットをそれぞれ表す。また、内標準としてTMSを用いた。
In the above table, * 1: Compound No. 248 is E-form, * 2: Compound No. 249 is Z-form.
Next, 1 H-NMR spectrum data is shown. In the following, “s” represents a singlet, “d” represents a doublet, “t” represents a triplet, “br” represents a broad singlet, “q” represents a quartet, and “m” represents a multiplet. Moreover, TMS was used as an internal standard.
(化合物番号12)
1H−NMR(CDCl3,δppm)0.90(t,3H),1.20−1.41(m,2H),1.28(s,3H),1.30(s,3H),1.46−1.82(m,2H),1.89−2.18(m,4H),2.47(s,3H),2.88(br,1H),3.30(q,2H),3.55(m,1H),4.84(br,1H),7.02(d,1H),7.31(d,1H)
(Compound No. 12)
1 H-NMR (CDCl 3 , δ ppm) 0.90 (t, 3H), 1.20-1.41 (m, 2H), 1.28 (s, 3H), 1.30 (s, 3H), 1.46-1.82 (m, 2H), 1.89-2.18 (m, 4H), 2.47 (s, 3H), 2.88 (br, 1H), 3.30 (q, 2H), 3.55 (m, 1H), 4.84 (br, 1H), 7.02 (d, 1H), 7.31 (d, 1H)
(化合物番号13)
1H−NMR(CDCl3,δppm)1.89−2.21(m,4H),2.51(s,3H),2.72(br,1H),3.32(q,2H),3.34(br,1H),4.95(br,1H),7.111(d,1H),7.36(d,1H),9.11(s,1H)
(Compound No. 13)
1 H-NMR (CDCl 3 , δ ppm) 1.89-2.21 (m, 4H), 2.51 (s, 3H), 2.72 (br, 1H), 3.32 (q, 2H), 3.34 (br, 1H), 4.95 (br, 1H), 7.111 (d, 1H), 7.36 (d, 1H), 9.11 (s, 1H)
(化合物番号30)
1H−NMR(CDCl3,δppm)2.07(m,4H),2.42(s,3H),3.38(q,2H),3.64(t,4H),6.54(s,1H),6.95(d,1H),8.25(d,1H)
(Compound No. 30)
1 H-NMR (CDCl 3 , δ ppm) 2.07 (m, 4H), 2.42 (s, 3H), 3.38 (q, 2H), 3.64 (t, 4H), 6.54 ( s, 1H), 6.95 (d, 1H), 8.25 (d, 1H)
(化合物番号33)
1H−NMR(CDCl3,δppm)2.31(m,2H),2.39(s,3H),3.39(q,2H),4.11(t,4H),6.04(s,1H),6.91(d,1H),8.37(d,1H)
(Compound No. 33)
1 H-NMR (CDCl 3 , δ ppm) 2.31 (m, 2H), 2.39 (s, 3H), 3.39 (q, 2H), 4.11 (t, 4H), 6.04 ( s, 1H), 6.91 (d, 1H), 8.37 (d, 1H)
(化合物番号47)
1H−NMR(CDCl3,δppm)1.33(t,3H),2.41(s,3H),3.38(q,2H),4.26(q,2H),6.73(s,1H),6.94(d,1H),8.27(d,1H)
(Compound No. 47)
1 H-NMR (CDCl 3 , δ ppm) 1.33 (t, 3H), 2.41 (s, 3H), 3.38 (q, 2H), 4.26 (q, 2H), 6.73 ( s, 1H), 6.94 (d, 1H), 8.27 (d, 1H)
(化合物番号48)
1H−NMR(CDCl3,δppm)3.36(q,2H),3.68(q,2H),7.97(s,1H),8.75(s,1H),9.45(s,1H)
(Compound No. 48)
1 H-NMR (CDCl 3 , δ ppm) 3.36 (q, 2H), 3.68 (q, 2H), 7.97 (s, 1H), 8.75 (s, 1H), 9.45 ( s, 1H)
(化合物番号51)
1H−NMR(CDCl3,δppm)2.18(m,4H),2.30(s,3H),3.28(q,2H),3.33(m,1H),3.76(m,1H),4.71(m,1H),7.42(s,1H),7.82(s,1H),8.38(s,1H)
(Compound No. 51)
1 H-NMR (CDCl 3 , δ ppm) 2.18 (m, 4H), 2.30 (s, 3H), 3.28 (q, 2H), 3.33 (m, 1H), 3.76 ( m, 1H), 4.71 (m, 1H), 7.42 (s, 1H), 7.82 (s, 1H), 8.38 (s, 1H)
(化合物番号52)
1H−NMR(CDCl3,δppm)2.41(s,3H),2.48(m,2H),3.39(q,2H),3.73(t,2H),3.85(t,2H),6.27(s,1H),6.94(d,1H),8.32(d,1H)
(Compound No. 52)
1 H-NMR (CDCl 3 , δ ppm) 2.41 (s, 3H), 2.48 (m, 2H), 3.39 (q, 2H), 3.73 (t, 2H), 3.85 ( t, 2H), 6.27 (s, 1H), 6.94 (d, 1H), 8.32 (d, 1H)
(化合物番号53)
1H−NMR(CDCl3,δppm)1.62(m,2H),1.89(m,1H),2.12(m,1H),2.35(m,1H),2.41(s,3H),2.88(m,1H),2.99(m,1H),3.38(q,2H),3.91(m,1H),4.36(m,1H),6.53(s,1H),6.94(d,1H),8.25(d,1H)
(Compound No. 53)
1 H-NMR (CDCl 3 , δ ppm) 1.62 (m, 2H), 1.89 (m, 1H), 2.12 (m, 1H), 2.35 (m, 1H), 2.41 ( s, 3H), 2.88 (m, 1H), 2.99 (m, 1H), 3.38 (q, 2H), 3.91 (m, 1H), 4.36 (m, 1H), 6.53 (s, 1H), 6.94 (d, 1H), 8.25 (d, 1H)
(化合物番号54)
1H−NMR(CDCl3,δppm)1.62(m,2H),1.97(m,2H),2.27(m,1H),2.41(s,3H),2.91(m,2H),3.38(q,2H),4.17(m,2H),6.51(s,1H),6.94(d,1H),8.27(d,1H)
(Compound No. 54)
1 H-NMR (CDCl 3 , δ ppm) 1.62 (m, 2H), 1.97 (m, 2H), 2.27 (m, 1H), 2.41 (s, 3H), 2.91 ( m, 2H), 3.38 (q, 2H), 4.17 (m, 2H), 6.51 (s, 1H), 6.94 (d, 1H), 8.27 (d, 1H)
(化合物番号56)
1H−NMR(CDCl3,δppm)1.98(m,2H),2.03(m,1H),2.34(s,3H),2.47(m,1H),3.35(q,2H),3.79(m,2H),4.88(m,1H),6.28(s,H),6.78(d,1H),7.35(m,5H),8.34(d,1H)
(Compound No. 56)
1 H-NMR (CDCl 3 , δ ppm) 1.98 (m, 2H), 2.03 (m, 1H), 2.34 (s, 3H), 2.47 (m, 1H), 3.35 ( q, 2H), 3.79 (m, 2H), 4.88 (m, 1H), 6.28 (s, H), 6.78 (d, 1H), 7.35 (m, 5H), 8.34 (d, 1H)
(化合物番号58)
1H−NMR(CDCl3,δppm)2.41(s,3H),2.69(m,4H),3.38(q,2H),3.81(m,4H),6.48(s,1H),6.94(d,1H),8.25(d,1H)
(Compound No. 58)
1 H-NMR (CDCl 3 , δ ppm) 2.41 (s, 3H), 2.69 (m, 4H), 3.38 (q, 2H), 3.81 (m, 4H), 6.48 ( s, 1H), 6.94 (d, 1H), 8.25 (d, 1H)
(化合物番号59)
1H−NMR(CDCl3,δppm)1.60(d,3H),2.41(s,3H),3.10(m,1H),3.28(m,1H),3.39(q,2H),3.74(m,1H),3.95(m,1H),5.35(q,1H),6.38(s,1H),6.94(d,1H),8.33(d,1H)
(Compound No. 59)
1 H-NMR (CDCl 3 , δ ppm) 1.60 (d, 3H), 2.41 (s, 3H), 3.10 (m, 1H), 3.28 (m, 1H), 3.39 ( q, 2H), 3.74 (m, 1H), 3.95 (m, 1H), 5.35 (q, 1H), 6.38 (s, 1H), 6.94 (d, 1H), 8.33 (d, 1H)
(化合物番号61)
1H−NMR(CDCl3,δppm)1.21(d,6H),2.41(s,3H),3.38(q,2H),3.44(t,2H),3.94(t,2H),4.24(m,1H),6.97(d,1H),8.42(d,1H),10.67(s,1H)
(Compound No. 61)
1 H-NMR (CDCl 3 , δ ppm) 1.21 (d, 6H), 2.41 (s, 3H), 3.38 (q, 2H), 3.44 (t, 2H), 3.94 ( t, 2H), 4.24 (m, 1H), 6.97 (d, 1H), 8.42 (d, 1H), 10.67 (s, 1H)
(化合物番号236)
1H−NMR(CDCl3,δppm)2.40(s,3H),3.41(s,3H),6.94(d,1H),7.19(d,1H),7.32(t,1H),7.45−7.53(m,2H),7.59(d,1H)
(Compound No. 236)
1 H-NMR (CDCl 3 , δ ppm) 2.40 (s, 3H), 3.41 (s, 3H), 6.94 (d, 1H), 7.19 (d, 1H), 7.32 ( t, 1H), 7.45-7.53 (m, 2H), 7.59 (d, 1H)
(化合物番号243)
1H−NMR(CDCl3,δppm)1.48(s,9H),1.94(m,3H),2.42(s,3H),2.51(m,1H),3.32(q,2H),3.43(m,2H),4.48(m,1H),6.95(d,1H),8.53(d,1H).9.50(s,1H)
(Compound No. 243)
1 H-NMR (CDCl 3 , δ ppm) 1.48 (s, 9H), 1.94 (m, 3H), 2.42 (s, 3H), 2.51 (m, 1H), 3.32 ( q, 2H), 3.43 (m, 2H), 4.48 (m, 1H), 6.95 (d, 1H), 8.53 (d, 1H). 9.50 (s, 1H)
(化合物番号244)
1H−NMR(CDCl3,δppm)2.08−2.21(m,3H),2.41(s,3H),2.55(m,1H),3.36(q,1H),3.49(m,2H),5.02(m ,1H),6.94(d,1H),8.10(d,1H),9.17(s,1H),11.04(s,1H)
(Compound No. 244)
1 H-NMR (CDCl 3 , δ ppm) 2.08-2.21 (m, 3H), 2.41 (s, 3H), 2.55 (m, 1H), 3.36 (q, 1H), 3.49 (m, 2H), 5.02 (m, 1H), 6.94 (d, 1H), 8.10 (d, 1H), 9.17 (s, 1H), 11.04 (s , 1H)
(化合物番号247)
1H−NMR(CDCl3,δppm)2.45(s,3H),3.19(q,2H),7.02(d,1H),7.04−7.09(m,2H),7.34(d,1H),7.39−7.47(m,2H)
(Compound No. 247)
1 H-NMR (CDCl 3 , δ ppm) 2.45 (s, 3H), 3.19 (q, 2H), 7.02 (d, 1H), 7.04-7.09 (m, 2H), 7.34 (d, 1H), 7.39-7.47 (m, 2H)
(化合物番号248)
1H−NMR(CDCl3,δppm)2.41(s,3H),3.31(q,2H),3.92−4.02(m,4H),6.95(d,1H),7.11(d,1H)
(Compound No. 248)
1 H-NMR (CDCl 3 , δ ppm) 2.41 (s, 3H), 3.31 (q, 2H), 3.92-4.02 (m, 4H), 6.95 (d, 1H), 7.11 (d, 1H)
(化合物番号254)
1H−NMR(CDCl3,δppm)1.86−2.23(m,4H),2.43(s,3H),3.33(q,2H),3.63(m,1H),4.03(m,1H),5.06(m,1H),6.99(d,1H),7.25(d,1H)
(Compound No. 254)
1 H-NMR (CDCl 3 , δ ppm) 1.86-2.23 (m, 4H), 2.43 (s, 3H), 3.33 (q, 2H), 3.63 (m, 1H), 4.03 (m, 1H), 5.06 (m, 1H), 6.99 (d, 1H), 7.25 (d, 1H)
(化合物番号258)
1H−NMR(CDCl3,δppm)1.32(m,1H),1.66(m,1H),2.25−2.30(m,2H),2.45(s,3H),3.40(q,2H),5.95(m,1H),7.04(d,1H),8.72(d,1H),8.78(s,1H)
(Compound No. 258)
1 H-NMR (CDCl 3 , δ ppm) 1.32 (m, 1H), 1.66 (m, 1H), 2.25-2.30 (m, 2H), 2.45 (s, 3H), 3.40 (q, 2H), 5.95 (m, 1H), 7.04 (d, 1H), 8.72 (d, 1H), 8.78 (s, 1H)
(化合物番号260)
1H−NMR(CDCl3,δppm)2.42(s,3H),3.31(q,2H),3.55−3.65(m,4H),3.89(s,3H),6.41(s,1H),6.97(d,1H),7.41(d,1H)
(Compound No. 260)
1 H-NMR (CDCl 3 , δ ppm) 2.42 (s, 3H), 3.31 (q, 2H), 3.55 to 3.65 (m, 4H), 3.89 (s, 3H), 6.41 (s, 1H), 6.97 (d, 1H), 7.41 (d, 1H)
(化合物番号261)
1H−NMR(CDCl3,δppm)1.27(s,9H),2.41(s,3H),3.31(q,2H),3.55−3.65(m,4H),6.45(s,1H),6.96(d,1H),7.44(d,1H)
(Compound No. 261)
1 H-NMR (CDCl 3 , δ ppm) 1.27 (s, 9H), 2.41 (s, 3H), 3.31 (q, 2H), 3.55 to 3.65 (m, 4H), 6.45 (s, 1H), 6.96 (d, 1H), 7.44 (d, 1H)
(化合物番号262)
1H−NMR(CDCl3,δppm)2.41(s,3H),3.29(q,2H),3.55−3.65(m,4H),4.94(s,2H),6.42(s,1H),6.95(d,1H),7.27−7.37(m,6H)
(Compound No. 262)
1 H-NMR (CDCl 3 , δ ppm) 2.41 (s, 3H), 3.29 (q, 2H), 3.55 to 3.65 (m, 4H), 4.94 (s, 2H), 6.42 (s, 1H), 6.95 (d, 1H), 7.27-7.37 (m, 6H)
(化合物番号263)
1H−NMR(CDCl3,δppm)2.42(s,3H),3.30(q,2H),3.55−3.65(m,4H),5.04(s,2H),6.31(s,1H),6.98(d,1H),7.31(d,1H)
(Compound No. 263)
1 H-NMR (CDCl 3 , δ ppm) 2.42 (s, 3H), 3.30 (q, 2H), 3.55 to 3.65 (m, 4H), 5.04 (s, 2H), 6.31 (s, 1H), 6.98 (d, 1H), 7.31 (d, 1H)
次に、これらの化合物を有効成分とする殺ダニ剤の製剤実施例を若干示すが、添加物及び添加割合は、これら実施例に限定されるべきものではなく、広範囲に変化させることが可能である。また、製剤実施例中の部は重量部を示す。 Next, formulation examples of acaricides containing these compounds as active ingredients are shown. However, the additives and addition ratios are not limited to these examples, and can be varied in a wide range. is there. Moreover, the part in a formulation Example shows a weight part.
製剤実施例1 水和剤
化合物(I) 40部
クレー 48部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 8部
以上を均一に混合して微細に粉砕し、有効成分40%の水和剤を得る。
Formulation Example 1 Wetting agent Compound (I) 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more are uniformly mixed and finely pulverized to hydrate 40% active ingredient Get the agent.
製剤実施例2 乳剤
化合物(I) 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解し、有効成分10%の乳剤を得る。
Formulation Example 2 Emulsion Compound (I) 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts The above components are mixed and dissolved to obtain an emulsion containing 10% active ingredient.
製剤実施例3 粉剤
化合物(I) 10部
クレー 90部
以上を均一に混合して微細に粉砕し、有効成分10%の粉剤を得る。
Formulation Example 3 Powder Compound (I) 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
製剤実施例4 粒剤
化合物(I) 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。
Formulation Example 4 Granules Compound (I) 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above is pulverized and mixed well, and water is added and kneaded well. Dry to obtain granules with 5% active ingredient.
製剤実施例5 懸濁剤
化合物(I) 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。
Formulation Example 5 Suspending agent Compound (I) 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Wet mill until the following content is obtained to obtain a 10% active ingredient suspension.
製剤実施例6 顆粒水和剤
化合物(I) 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
5部
以上を均一に混合して微細に粉砕後、適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分40%の水和剤を得る。
Formulation Example 6 Granule wettable compound Compound (I) 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt
After mixing 5 parts or more uniformly and finely pulverizing, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient.
得られた本発明の殺ダニ剤の試験例を以下に示す。
(試験例1)ナミハダニに対する効力
3寸鉢に播種したインゲンの発芽後7〜10日を経過した第1本葉上に、有機リン剤抵抗性のナミハダニ雌成虫を17頭接種したのち、製剤実施例1に示された処方に従い得た水和剤を、化合物濃度が125ppmになるように水で希釈した薬液を散布した。温度25℃、湿度65%の恒温室内に置き、3日後に殺成虫率を調査した。試験は2反復である。その結果、以下の化合物が100%の殺ダニ率を示した。
Test examples of the obtained acaricide of the present invention are shown below.
(Test Example 1) Efficacy against the spider mite On the first true leaf 7 to 10 days after germination of the green beans seeded in a three-size pot, inoculate 17 female adult spider mite that are resistant to organophosphates and then carry out the formulation. The wettable powder obtained according to the formulation shown in Example 1 was sprayed with a chemical diluted with water so that the compound concentration was 125 ppm. It was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%, and the rate of killing insects was examined after 3 days. The test is duplicated. As a result, the following compounds showed a miticide rate of 100%.
化合物番号:1、3、4、6、7、9、10、11、13、29、30、35、36、39、40、42、43、52、53、54、56、57、59、64、65、238、239、240、247、248、249、250、257、258、263
対照に用いたクロルジメフォルムの殺ダニ率は40%であった。
Compound numbers: 1, 3, 4, 6, 7, 9, 10, 11, 13, 29, 30, 35, 36, 39, 40, 42, 43, 52, 53, 54, 56, 57, 59, 64 , 65, 238, 239, 240, 247, 248, 249, 250, 257, 258, 263
The miticide rate of chlordiform used as a control was 40%.
(試験例2)フタトゲチマダニ(Haemaphysalis longicornis)に対する効力
20mL容のガラスバイアル瓶を試験前日までにアセトンで良く洗浄し試験に用いた。
試験化合物をアセトンで4000ppmに溶解し、更にアセトンで公比10の希釈溶液を調製した。
バイアル瓶にアセトン溶液0.118mLを加え、ドライヤーで送風しながらバイアル瓶を回転させてアセトンを揮散させて化合物の薄膜を形成させた(400ppm溶液を用いたとき、1μg/cm2となる)。
(Test Example 2) Efficacy against Haemaphysalis longicornis A 20 mL glass vial was thoroughly washed with acetone by the day before the test and used for the test.
The test compound was dissolved in acetone at 4000 ppm, and a diluted solution having a common ratio of 10 was further prepared with acetone.
0.118 mL of an acetone solution was added to the vial, and the vial was rotated while blowing with a dryer to volatilize acetone to form a thin film of the compound (when using a 400 ppm solution, the concentration was 1 μg / cm 2 ).
この中に、幼ダニ(15−40頭/バイアル)を接種して速やかに蓋を閉じ、マダニの動きが落ち着いてから供試個体数を計数した。このとき不健全な個体を除外した。
以後観察室(25℃、暗黒下)に5日間放置し、経時的に生死判定を行い、殺虫率を算出した。その結果、以下の化合物が90%以上の殺虫率を示した。
化合物番号:3、4、6、10
In this, young ticks (15-40 heads / vial) were inoculated, the lid was quickly closed, and the number of test individuals was counted after the movement of ticks settled down. At this time, unhealthy individuals were excluded.
Thereafter, the sample was left in an observation room (25 ° C., in the dark) for 5 days, and a life-and-death determination was performed over time, and an insecticidal rate was calculated. As a result, the following compounds showed an insecticidal rate of 90% or more.
Compound numbers: 3, 4, 6, 10
Claims (2)
R2は、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。
R3は、水素原子、ハロゲン原子、ニトロ基、水酸基、メルカプト基、無置換若しくは置換基を有するアミノ基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC2〜20アルケニル基、無置換若しくは置換基を有するC2〜20アルキニル基、無置換若しくは置換基を有するアリール基、無置換若しくは置換基を有するC1〜20アシル基、無置換若しくは置換基を有するC1〜20チオアシル基、無置換若しくは置換基を有するC1〜20アルコキシ基、無置換若しくは置換基を有するC2〜20アルケニルオキシ基、無置換若しくは置換基を有するC2〜20アルキニルオキシ基、無置換若しくは置換基を有するアリールオキシ基、無置換若しくは置換基を有するヘテロイルオキシ基、無置換若しくは置換基を有するC1〜20アルキルチオ基、無置換若しくは置換基を有するC2〜20アルケニルチオ基、無置換若しくは置換基を有するC2〜20アルキニルチオ基、無置換若しくは置換基を有するアリールチオ基、無置換若しくは置換基を有するヘテロイルチオ基、無置換若しくは置換基を有するC1〜20アルキルスルフィニル基、無置換若しくは置換基を有するアリールスルフィニル基、無置換若しくは置換基を有するC1〜20アルキルスルホニル基、無置換若しくは置換基を有するアリールスルホニル基、又は、無置換若しくは置換基を有するヘテロ環基を表す。
R4は、水素原子、シアノ基、ホルミル基、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するC1〜20アシル基、又は、無置換若しくは置換基を有するフェニル基を表す。
R5は、無置換若しくは置換基を有するC1〜20アルキル基、無置換若しくは置換基を有するアミノ基、式(a)
Xは、式:N−CNで表される基、又は式:N−OR’(R’は水素原子又は無置換若しくは置換基を有するC1〜20アルキル基を示す。)で表される基を表し、
nは0又は1を表し、mは0を表す。
Aは酸素原子、硫黄原子、又は、式:N−Q(Qは、シアノ基、無置換若しくは置換基を有するC1〜20アルキル基、又は式:OR10で表される基を示す。R10は、水素原子、無置換若しくは置換基を有するC1〜10アルキル基を示す。)で表される基を表す。〕
で示される化合物又はその塩の少なくとも一種を有効成分として含有することを特徴とする殺ダニ剤。 Formula (I)
R 2 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C2 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, unsubstituted or substituted C1-20 A thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted group Aryloxy group, unsubstituted or substituted heteroyloxy group, unsubstituted Or a substituted C1-20 alkylthio group, an unsubstituted or substituted C2-20 alkenylthio group, an unsubstituted or substituted C2-20 alkynylthio group, an unsubstituted or substituted arylthio group, Unsubstituted or substituted heteroylthio group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, none A substituted or substituted arylsulfonyl group or an unsubstituted or substituted heterocyclic group is represented.
R 3 represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 2- 20 alkenyl group, unsubstituted or substituted C2-20 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted C1-20 acyl group, unsubstituted or substituted C1-20 A thioacyl group, an unsubstituted or substituted C1-20 alkoxy group, an unsubstituted or substituted C2-20 alkenyloxy group, an unsubstituted or substituted C2-20 alkynyloxy group, an unsubstituted or substituted group Aryloxy group, unsubstituted or substituted heteroyloxy group, unsubstituted Or a substituted C1-20 alkylthio group, an unsubstituted or substituted C2-20 alkenylthio group, an unsubstituted or substituted C2-20 alkynylthio group, an unsubstituted or substituted arylthio group, Unsubstituted or substituted heteroylthio group, unsubstituted or substituted C1-20 alkylsulfinyl group, unsubstituted or substituted arylsulfinyl group, unsubstituted or substituted C1-20 alkylsulfonyl group, none A substituted or substituted arylsulfonyl group or an unsubstituted or substituted heterocyclic group is represented.
R 4 is a hydrogen atom, a cyano group, a formyl group, an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted C1-20 acyl group, or an unsubstituted or substituted phenyl group Represents.
R 5 represents an unsubstituted or substituted C1-20 alkyl group, an unsubstituted or substituted amino group, the formula (a)
X represents a group represented by the formula: N—CN, or a group represented by the formula: N—OR ′ (R ′ represents a hydrogen atom or an unsubstituted or substituted C1-20 alkyl group). Represent,
n represents 0 or 1 , and m represents 0 .
A represents an oxygen atom, a sulfur atom, or a group represented by the formula: NQ (Q is a cyano group, an unsubstituted or substituted C1-20 alkyl group, or a formula: OR 10 ; R 10. Represents a hydrogen atom, an unsubstituted or substituted C1-10 alkyl group having a substituent. ]
A miticide that contains at least one of the compounds represented by the above or a salt thereof as an active ingredient.
R21は、無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキル基を表す。
R 3 は、水素原子、ハロゲン原子、ニトロ基、水酸基、メルカプト基;アミノ基;モノC1〜C6アルキルアミノ基;ジC1〜C6アルキルアミノ基;アシルアミノ基;フェニルアミノ基、4−メチルフェニルアミノ基;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキル基;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルケニル基、無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルキニル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリール基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アシル基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20チオアシル基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルコキシ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルケニルオキシ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルキニルオキシ基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリールオキシ基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)ヘテロイルオキシ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキルチオ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルケニルチオ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルキニルチオ基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリールチオ基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)ヘテロイルチオ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキルスルフィニル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリールスルフィニル基;無置換、又は(ハロゲン原子;フェニル基、4−メチルフェニル基で置換された)C1〜20アルキルスルホニル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリールスルホニル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)ヘテロ環基;を表す。
R 4 は、水素原子、シアノ基、ホルミル基;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキル基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アシル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)フェニル基;を表す。
R 6 、R 7 はそれぞれ独立して、水素原子;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキル基;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルケニル基;無置換、又は(ハロゲン原子、C1〜6アルコキシ基、フェニル基、若しくは4−メチルフェニル基で置換された)C2〜20アルキニル基;無置換、又は(C1〜6アルキル基、C1〜6ハロアルキル基、ハロゲン原子、C1〜6アルコキシ基、フェニル基、4−メトキシフェニル基、若しくはニトロ基で置換された)アリール基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルコキシ基;無置換、又は(ハロゲン原子、フェニル基、若しくは4−メチルフェニル基で置換された)C1〜20アルキルチオ基を表す。また、R6、R7は一緒になって;無置換若しくは置換基を有する4〜8員環を形成してもよい。さらに、該4〜8員環は、環内に、式:−N(R4)−C(=O)−で表される基に結合する窒素原子以外にヘテロ原子を含んでいてもよい。)
で示されるウレア化合物又はその塩。 Formula (I-1)
R 21 represents an unsubstituted or C1-20 alkyl group ( substituted with a halogen atom, a C1-6 alkoxy group, a phenyl group, or a 4-methylphenyl group).
R 3 is a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, a mercapto group; an amino group; a mono C1-C6 alkylamino group; a diC1-C6 alkylamino group; an acylamino group; a phenylamino group, a 4-methylphenylamino group. Unsubstituted or C1-20 alkyl group (substituted with a halogen atom, C1-6 alkoxy group, phenyl group or 4-methylphenyl group); unsubstituted or (halogen atom, C1-6 alkoxy group, phenyl; Group, or a C2-20 alkenyl group (substituted with a 4-methylphenyl group), unsubstituted, or C2-20 (substituted with a halogen atom, a C1-6 alkoxy group, a phenyl group, or a 4-methylphenyl group) Alkynyl group: unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy Aryl group substituted with a xy group, phenyl group, 4-methoxyphenyl group, or nitro group; unsubstituted or C1-20 acyl group (substituted with a halogen atom, phenyl group, or 4-methylphenyl group) Unsubstituted or substituted with a C1-20 thioacyl group (substituted with a halogen atom, phenyl group or 4-methylphenyl group); unsubstituted or substituted with a halogen atom, phenyl group or 4-methylphenyl group; C1-20 alkoxy group; unsubstituted or C2-20 alkenyloxy group (substituted with a halogen atom, phenyl group, or 4-methylphenyl group); unsubstituted or (halogen atom, phenyl group, or 4- C2-20 alkynyloxy group (substituted with methylphenyl group); unsubstituted or (C1-6 alkyl group, C1-6) A cycloalkyl group, a halogen atom, a C1-6 alkoxy group, a phenyl group, a 4-methoxyphenyl group, or an aryloxy group substituted with a nitro group; unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group); Heteroyloxy group substituted with a halogen atom, C1-6 alkoxy group, phenyl group, 4-methoxyphenyl group, or nitro group; unsubstituted or substituted with a halogen atom, phenyl group, or 4-methylphenyl group C1-20 alkylthio group; unsubstituted or C2-20 alkenylthio group (substituted with a halogen atom, phenyl group, or 4-methylphenyl group); unsubstituted or (halogen atom, phenyl group, or C2-20 alkynylthio group (substituted with 4-methylphenyl group); unsubstituted or (C1-6) An arylthio group substituted with a rualkyl group, a C1-6 haloalkyl group, a halogen atom, a C1-6 alkoxy group, a phenyl group, a 4-methoxyphenyl group, or a nitro group; unsubstituted or (C1-6 alkyl group, C1 ~ 6 haloalkyl group, halogen atom, C1-6 alkoxy group, phenyl group, 4-methoxyphenyl group, or heteroylthio group substituted by nitro group; unsubstituted or (halogen atom, phenyl group, or 4-methylphenyl) C1-20 alkylsulfinyl group substituted by a group; unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy group, phenyl group, 4-methoxyphenyl group, or nitro Arylsulfinyl group substituted by a group; unsubstituted or (halogen atom; phenyl) Group, C1-20 alkylsulfonyl group substituted by 4-methylphenyl group; unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy group, phenyl group, 4- Arylsulfonyl group substituted by methoxyphenyl group or nitro group; unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy group, phenyl group, 4-methoxyphenyl group) Or a heterocyclic group substituted with a nitro group.
R 4 represents a hydrogen atom, a cyano group, a formyl group; unsubstituted or a C 1-20 alkyl group (substituted with a halogen atom, a C 1-6 alkoxy group, a phenyl group, or a 4-methylphenyl group); Or a C1-20 acyl group (substituted with a halogen atom, phenyl group, or 4-methylphenyl group); unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy group) , A phenyl group, substituted with a phenyl group, a 4-methoxyphenyl group, or a nitro group).
R 6 and R 7 are each independently a hydrogen atom; unsubstituted or a C 1-20 alkyl group (substituted with a halogen atom, a C 1-6 alkoxy group, a phenyl group, or a 4-methylphenyl group); Or a C2-20 alkenyl group (substituted with a halogen atom, C1-6 alkoxy group, phenyl group, or 4-methylphenyl group); unsubstituted or (halogen atom, C1-6 alkoxy group, phenyl group, or C2-20 alkynyl group substituted by 4-methylphenyl group; unsubstituted or (C1-6 alkyl group, C1-6 haloalkyl group, halogen atom, C1-6 alkoxy group, phenyl group, 4-methoxyphenyl group) Or an aryl group substituted with a nitro group; unsubstituted or (with a halogen atom, a phenyl group, or a 4-methylphenyl group) An unsubstituted, or (halogen atom, a phenyl group, or substituted with a 4-methylphenyl group) C1-20 alkylthio group; conversion has been) C1-20 alkoxy groups. R 6 and R 7 may be combined together to form an unsubstituted or substituted 4- to 8-membered ring. Further, the 4- to 8-membered ring may contain a hetero atom in addition to the nitrogen atom bonded to the group represented by the formula: —N (R 4 ) —C (═O) —. )
Or a salt thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009191045A JP5280972B2 (en) | 2009-08-20 | 2009-08-20 | Acaricides and new urea compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009191045A JP5280972B2 (en) | 2009-08-20 | 2009-08-20 | Acaricides and new urea compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011042611A JP2011042611A (en) | 2011-03-03 |
JP5280972B2 true JP5280972B2 (en) | 2013-09-04 |
Family
ID=43830313
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009191045A Expired - Fee Related JP5280972B2 (en) | 2009-08-20 | 2009-08-20 | Acaricides and new urea compounds |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5280972B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021056922A1 (en) * | 2019-09-23 | 2021-04-01 | 山东康乔生物科技有限公司 | Aryl sulfide containing benzylamine structure, synthesis method therefor and application thereof |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2606726A1 (en) * | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituted trifluoroethylsulfide derivatives as acaricides and insecticides |
EP2816896B1 (en) * | 2012-02-21 | 2016-09-07 | Bayer Intellectual Property GmbH | Herbicidally active sulfinimidoyl- and sulfonimidoylbenzoyl derivatives |
BR112014020123B8 (en) * | 2012-02-21 | 2021-02-09 | Bayer Ip Gmbh | 3-(sulfin/sulfonimidoyl) benzamide compound, herbicide composition, its uses and method for controlling unwanted plants |
JP2016508972A (en) | 2012-12-20 | 2016-03-24 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Aryl sulfide and aryl sulfoxide derivatives as acaricides and insecticides |
ES2761571T3 (en) | 2013-06-20 | 2020-05-20 | Bayer Cropscience Ag | Arylsulfide and arylsulfoxide derivatives as acaricides and insecticides |
US9981928B2 (en) | 2013-06-20 | 2018-05-29 | Bayer Cropscience Aktiengesellschaft | Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides |
EP3019481B1 (en) | 2013-07-08 | 2019-03-06 | Bayer CropScience Aktiengesellschaft | Six-membered c-n linked arylsulfide and arylsulfoxide derivatives as pesticides |
WO2018015797A1 (en) | 2016-07-18 | 2018-01-25 | Insecticides (India) Limited | Novel benzylamide compound, method for producing the same, and miticide |
KR102348155B1 (en) * | 2016-07-18 | 2022-01-06 | 오에이티 아그리오 가부시키가이샤 | Novel benzylamide compounds, methods for their preparation, and acaricides |
WO2018051252A2 (en) | 2016-09-15 | 2018-03-22 | Insecticides (India) Limited | Novel amide compound, method for producing the same, and miticide |
CN111978225B (en) * | 2018-06-05 | 2022-03-04 | 沈阳化工大学 | Trifluoroethyl sulfide (sulfoxide) substituted benzene compound and application thereof |
TWI818061B (en) * | 2018-08-20 | 2023-10-11 | 日商住友化學股份有限公司 | Amide compound and use thereof |
CN111253333A (en) * | 2018-11-30 | 2020-06-09 | 青岛清原化合物有限公司 | N- (1,3, 4-oxadiazole-2-yl) aryl formamide or salt thereof, preparation method, herbicidal composition and application |
JP2022116370A (en) * | 2019-06-13 | 2022-08-10 | アグロカネショウ株式会社 | Novel 1-benzylamine derivative and agricultural and horticultural agents with the same as active ingredient |
CN112142646B (en) * | 2019-06-26 | 2022-08-09 | 沈阳中化农药化工研发有限公司 | Pyrrolo-aromatic ring compounds and application thereof |
CN114072391A (en) | 2019-07-10 | 2022-02-18 | 拜耳公司 | Process for preparing 2- (phenylimino) -1, 3-thiazolidin-4-ones |
CN114040910A (en) | 2019-07-10 | 2022-02-11 | 拜耳公司 | Process for preparing 2- (phenylimino) -1, 3-thiazolidin-4-ones |
EP4013744A1 (en) | 2019-08-15 | 2022-06-22 | Bayer Aktiengesellschaft | Process of preparing 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-ones |
MX2022010058A (en) | 2020-02-18 | 2022-08-25 | Bayer Ag | Process of preparing 2-(phenylimino)-3-alkyl-1,3-thiazolidin-4-on es. |
WO2022166837A1 (en) * | 2021-02-07 | 2022-08-11 | 山东康乔生物科技有限公司 | Aryl sulfide, preparation method therefor, and application thereof |
CN115701423A (en) * | 2021-08-02 | 2023-02-10 | 沈阳化工大学 | Preparation method of trifluoroethyl sulfide (sulfoxide) substituted benzene compound and intermediate thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS598272B2 (en) * | 1975-12-17 | 1984-02-23 | 住友化学工業株式会社 | Nyosoyuudou Taino Seizouhou |
JP2007308392A (en) * | 2006-05-16 | 2007-11-29 | Bayer Cropscience Ag | Insecticidal benzamidines |
-
2009
- 2009-08-20 JP JP2009191045A patent/JP5280972B2/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021056922A1 (en) * | 2019-09-23 | 2021-04-01 | 山东康乔生物科技有限公司 | Aryl sulfide containing benzylamine structure, synthesis method therefor and application thereof |
JP2022531823A (en) * | 2019-09-23 | 2022-07-12 | 山東康喬生物科技有限公司 | Aryl sulfides containing a benzylamine structure and their synthetic methods and applications |
JP7303893B2 (en) | 2019-09-23 | 2023-07-05 | 山東康喬生物科技有限公司 | Aryl sulfide containing benzylamine structure and its synthesis method and application |
AU2020356739B2 (en) * | 2019-09-23 | 2023-12-07 | Shandong Kangqiao Bio-Technology Co., Ltd | Aryl sulfide containing benzylamine structure, synthesis method therefor and application thereof |
Also Published As
Publication number | Publication date |
---|---|
JP2011042611A (en) | 2011-03-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5280972B2 (en) | Acaricides and new urea compounds | |
JP5307819B2 (en) | Nitrogen-containing heterocyclic compounds and pest control agents | |
MX2009000144A (en) | Pest control agent containing novel pyridyl-methanamine derivative or salt thereof. | |
TWI771410B (en) | N-(4-pyridyl)nicotinamide compound or salt thereof | |
US20110195930A1 (en) | Pyridine derivative or its salt, pesticide containing it and process for its production | |
WO2017222037A1 (en) | N-(4-pyridyl)benzamide compound or salt thereof, and pest control agent containing compound or salt thereof as active ingredient | |
WO2010100876A1 (en) | Tetrazoyl oxime derivative, salt thereof, and plant disease control agent | |
JP6432514B2 (en) | Pest control agent | |
WO2016068301A1 (en) | Pest control agent | |
JP5542452B2 (en) | Tetrazoyloxime derivatives and salts thereof, and plant disease control agents | |
JP2016204325A (en) | Pest control agent | |
JP2009062277A (en) | Benzisothiazoline compound and pest control agent | |
JP2018145187A (en) | Pest control agent containing substituted pyridine compound or salt thereof as active ingredient | |
JP2018193363A (en) | Pest control agent containing isoindolinone compound or salt thereof as active ingredient | |
JP2017008029A (en) | Pest control agent comprising n-(4-pyridyl)picoline amide compound or salt thereof as active ingredient | |
WO2017200100A1 (en) | N-(4-pyridyl) benzamide compound or salt thereof, and pest control agent containing said compound or salt thereof as active ingredient | |
JP2019081709A (en) | Pest control agent | |
WO2019163921A1 (en) | Substituted pyridine compound and salt thereof | |
JP2018197192A (en) | Pest controlling agent containing thienopyrrole-based compound and salt thereof as active ingredients | |
JP2016164150A (en) | Pest control agent | |
JP2016014016A (en) | Pest control agent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120523 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130218 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130226 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130422 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130521 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130523 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5280972 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |