DD295632A5 - Thioxotetrazoline - Google Patents

Thioxotetrazoline Download PDF

Info

Publication number: DD295632A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; ind; phenyl; thioxo; tetrazoline
Prior art date: 1989-06-26

Application number

DD90342037A

Other languages

German (de)

English (en)

Inventor

Josef Ehrenfreund

Erich Stamm

Original Assignee

��`��@��k��

Priority date (The priority date 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 date listed.)

1989-06-26

Filing date

1990-06-25

Publication date

1991-11-07

1990-06-25 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1991-11-07 Publication of DD295632A5 publication Critical patent/DD295632A5/de

Links

-1 cyano, hydroxy Chemical group 0.000 claims abstract description 75
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 39
150000002367 halogens Chemical group 0.000 claims abstract description 34
229910052736 halogen Inorganic materials 0.000 claims abstract description 33
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 30
125000001424 substituent group Chemical group 0.000 claims abstract description 26
150000002431 hydrogen Chemical class 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical class SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 5
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
241000239223 Arachnida Species 0.000 claims abstract description 4
125000005059 halophenyl group Chemical group 0.000 claims abstract description 4
125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims abstract 6
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 24
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
230000008569 process Effects 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 3
241000238631 Hexapoda Species 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
238000006462 rearrangement reaction Methods 0.000 claims description 3
NNSBMMXJLYWCMW-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-[4-phenoxy-2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(CC(C)(C)C)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1 NNSBMMXJLYWCMW-UHFFFAOYSA-N 0.000 claims description 2
CTHOEBAHIHBQOW-UHFFFAOYSA-N 1-(2-cyclopentyl-4-phenoxy-6-propan-2-ylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound C=1C(C2CCCC2)=C(N2C(N(C(C)C)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1 CTHOEBAHIHBQOW-UHFFFAOYSA-N 0.000 claims description 2
HZWBABPIHOHSIR-UHFFFAOYSA-N 1-(2-cyclopentyl-6-propan-2-ylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound N1=NN(C(C)C)C(=S)N1C=1C(C(C)C)=CC=CC=1C1CCCC1 HZWBABPIHOHSIR-UHFFFAOYSA-N 0.000 claims description 2
WOOIQPGPLSPERO-UHFFFAOYSA-N 1-(2-ethyl-6-propan-2-ylphenyl)-4-methyltetrazole-5-thione Chemical compound CCC1=CC=CC(C(C)C)=C1N1C(=S)N(C)N=N1 WOOIQPGPLSPERO-UHFFFAOYSA-N 0.000 claims description 2
JBDXOWJQLDXJJA-UHFFFAOYSA-N 1-(2-ethyl-6-propan-2-ylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound CCC1=CC=CC(C(C)C)=C1N1C(=S)N(C(C)C)N=N1 JBDXOWJQLDXJJA-UHFFFAOYSA-N 0.000 claims description 2
DHJCXVISTUDYLP-UHFFFAOYSA-N 1-(2-tert-butyl-6-methylphenyl)-4-(2,2-dimethylpropyl)tetrazole-5-thione Chemical compound CC1=CC=CC(C(C)(C)C)=C1N1C(=S)N(CC(C)(C)C)N=N1 DHJCXVISTUDYLP-UHFFFAOYSA-N 0.000 claims description 2
KTQJBGHXJGOSIC-UHFFFAOYSA-N 1-(2-tert-butyl-6-methylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound S=C1N(C(C)C)N=NN1C1=C(C)C=CC=C1C(C)(C)C KTQJBGHXJGOSIC-UHFFFAOYSA-N 0.000 claims description 2
GMYJYWZRUWEJCQ-UHFFFAOYSA-N 1-[4-(1-phenylethyl)-2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazole-5-thione Chemical compound CC(C)C1=CC(C(C)C=2C=CC=CC=2)=CC(C(C)C)=C1N1N=NN(C(C)C)C1=S GMYJYWZRUWEJCQ-UHFFFAOYSA-N 0.000 claims description 2
HVIQPCXPVHNYBH-UHFFFAOYSA-N 1-[4-phenoxy-2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(C(C)C)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1 HVIQPCXPVHNYBH-UHFFFAOYSA-N 0.000 claims description 2
JZGFVARBUSUQLY-UHFFFAOYSA-N 1-butan-2-yl-4-(2-tert-butyl-6-methylphenyl)tetrazole-5-thione Chemical compound S=C1N(C(C)CC)N=NN1C1=C(C)C=CC=C1C(C)(C)C JZGFVARBUSUQLY-UHFFFAOYSA-N 0.000 claims description 2
FYYACQQSYSDVJB-UHFFFAOYSA-N 1-phenyl-2h-tetrazol-5-one Chemical compound OC1=NN=NN1C1=CC=CC=C1 FYYACQQSYSDVJB-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
LHCBAHNHNGEGGG-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-(2-ethyl-6-propan-2-ylphenyl)tetrazole-5-thione Chemical compound CCC1=CC=CC(C(C)C)=C1N1C(=S)N(CC(C)(C)C)N=N1 LHCBAHNHNGEGGG-UHFFFAOYSA-N 0.000 claims 1
KUEWJKRRIUCATF-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-(2-methyl-6-propan-2-ylphenyl)tetrazole-5-thione Chemical compound CC(C)C1=CC=CC(C)=C1N1C(=S)N(CC(C)(C)C)N=N1 KUEWJKRRIUCATF-UHFFFAOYSA-N 0.000 claims 1
FSAHNPRNIFGLDB-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-[2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=S)N(CC(C)(C)C)N=N1 FSAHNPRNIFGLDB-UHFFFAOYSA-N 0.000 claims 1
WFQKCOQNPCEBIV-UHFFFAOYSA-N 1-(2-methyl-6-propan-2-ylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound CC(C)C1=CC=CC(C)=C1N1C(=S)N(C(C)C)N=N1 WFQKCOQNPCEBIV-UHFFFAOYSA-N 0.000 claims 1
HOPNCSZBFAHBAZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-[4-phenoxy-2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(CC3CC3)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1 HOPNCSZBFAHBAZ-UHFFFAOYSA-N 0.000 claims 1
AMPDHWBXDPQGOO-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-4-(1-methoxypropan-2-yl)tetrazole-5-thione Chemical compound S=C1N(C(C)COC)N=NN1C1=C(C(C)C)C=CC=C1C(C)C AMPDHWBXDPQGOO-UHFFFAOYSA-N 0.000 claims 1
HSWUCQGMGVAJJN-UHFFFAOYSA-N 1-[4-(2-fluorophenoxy)-2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(C(C)C)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1F HSWUCQGMGVAJJN-UHFFFAOYSA-N 0.000 claims 1
UOYQUBRBRPOWKT-UHFFFAOYSA-N 1-[4-benzyl-2,6-di(propan-2-yl)phenyl]-4-(2,2-dimethylpropyl)tetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(CC(C)(C)C)N=N2)=S)C(C(C)C)=CC=1CC1=CC=CC=C1 UOYQUBRBRPOWKT-UHFFFAOYSA-N 0.000 claims 1
ZZMIZIBMFCTUPJ-UHFFFAOYSA-N 1-[4-benzyl-2,6-di(propan-2-yl)phenyl]-4-butan-2-yltetrazole-5-thione Chemical compound S=C1N(C(C)CC)N=NN1C(C(=C1)C(C)C)=C(C(C)C)C=C1CC1=CC=CC=C1 ZZMIZIBMFCTUPJ-UHFFFAOYSA-N 0.000 claims 1
MWPAZNVQATUWHU-UHFFFAOYSA-N 1-[4-benzyl-2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(C(C)C)N=N2)=S)C(C(C)C)=CC=1CC1=CC=CC=C1 MWPAZNVQATUWHU-UHFFFAOYSA-N 0.000 claims 1
ZHAXCAAOPRTWFM-UHFFFAOYSA-N 1-butan-2-yl-4-(2-cyclopentyl-6-propan-2-ylphenyl)tetrazole-5-thione Chemical compound S=C1N(C(C)CC)N=NN1C1=C(C(C)C)C=CC=C1C1CCCC1 ZHAXCAAOPRTWFM-UHFFFAOYSA-N 0.000 claims 1
PBIHEKAMOGQUMY-UHFFFAOYSA-N 1-butan-2-yl-4-(2-methyl-6-propan-2-ylphenyl)tetrazole-5-thione Chemical compound S=C1N(C(C)CC)N=NN1C1=C(C)C=CC=C1C(C)C PBIHEKAMOGQUMY-UHFFFAOYSA-N 0.000 claims 1
OMFICDHQNRAHKG-UHFFFAOYSA-N 1-cyclohex-2-en-1-yl-4-[2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=S)N(C2C=CCCC2)N=N1 OMFICDHQNRAHKG-UHFFFAOYSA-N 0.000 claims 1
NFRCAFXAARWQSD-UHFFFAOYSA-N 1-cyclopentyl-4-[4-phenoxy-2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound C=1C(C(C)C)=C(N2C(N(C3CCCC3)N=N2)=S)C(C(C)C)=CC=1OC1=CC=CC=C1 NFRCAFXAARWQSD-UHFFFAOYSA-N 0.000 claims 1
GWJFQRQGPHWMCG-UHFFFAOYSA-N 1-ethyl-4-[4-phenoxy-2,6-di(propan-2-yl)phenyl]tetrazole-5-thione Chemical compound S=C1N(CC)N=NN1C(C(=C1)C(C)C)=C(C(C)C)C=C1OC1=CC=CC=C1 GWJFQRQGPHWMCG-UHFFFAOYSA-N 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
125000004966 cyanoalkyl group Chemical group 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 abstract description 3
239000000575 pesticide Substances 0.000 abstract description 3
PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 abstract description 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 35
230000000694 effects Effects 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000012360 testing method Methods 0.000 description 18
230000009471 action Effects 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 14
239000000839 emulsion Substances 0.000 description 14
230000009467 reduction Effects 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
241000196324 Embryophyta Species 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
239000011737 fluorine Substances 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
239000004094 surface-active agent Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
239000007921 spray Substances 0.000 description 10
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
240000001307 Myosotis scorpioides Species 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000004033 plastic Substances 0.000 description 9
229920003023 plastic Polymers 0.000 description 9
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
238000011156 evaluation Methods 0.000 description 8
239000008187 granular material Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
238000005507 spraying Methods 0.000 description 8
239000005995 Aluminium silicate Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
240000007594 Oryza sativa Species 0.000 description 7
239000000654 additive Substances 0.000 description 7
235000012211 aluminium silicate Nutrition 0.000 description 7
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000000304 alkynyl group Chemical group 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
241001556089 Nilaparvata lugens Species 0.000 description 5
239000013543 active substance Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
238000009472 formulation Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
241000464975 Crocidolomia pavonana Species 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
230000000895 acaricidal effect Effects 0.000 description 4
239000000642 acaricide Substances 0.000 description 4
238000007792 addition Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000002736 nonionic surfactant Substances 0.000 description 4
125000003884 phenylalkyl group Chemical group 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
WLCKWAKHQIWFIR-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-2h-tetrazol-5-one Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=O)NN=N1 WLCKWAKHQIWFIR-UHFFFAOYSA-N 0.000 description 3
ONDYDIFEKZRYEJ-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazol-5-one Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=O)N(C(C)C)N=N1 ONDYDIFEKZRYEJ-UHFFFAOYSA-N 0.000 description 3
OFTVCVGPFQJAIO-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-4-propan-2-yltetrazole-5-thione Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=S)N(C(C)C)N=N1 OFTVCVGPFQJAIO-UHFFFAOYSA-N 0.000 description 3
241000238876 Acari Species 0.000 description 3
241000952611 Aphis craccivora Species 0.000 description 3
241001529600 Diabrotica balteata Species 0.000 description 3
240000001624 Espostoa lanata Species 0.000 description 3
235000009161 Espostoa lanata Nutrition 0.000 description 3
241000256244 Heliothis virescens Species 0.000 description 3
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 3
229920001732 Lignosulfonate Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
241000238680 Rhipicephalus microplus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000256250 Spodoptera littoralis Species 0.000 description 3
241001454293 Tetranychus urticae Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
229940117389 dichlorobenzene Drugs 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 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
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000004546 suspension concentrate Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000007280 thionation reaction Methods 0.000 description 3
125000006017 1-propenyl group Chemical group 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
241000254177 Anthonomus Species 0.000 description 2
241000254175 Anthonomus grandis Species 0.000 description 2
241001124076 Aphididae Species 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 2
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
241000931705 Cicada Species 0.000 description 2
241000254137 Cicadidae Species 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241000060469 Eupoecilia ambiguella Species 0.000 description 2
240000002024 Gossypium herbaceum Species 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000358422 Nephotettix cincticeps Species 0.000 description 2
241000721454 Pemphigus Species 0.000 description 2
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
241001481703 Rhipicephalus <genus> Species 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
241001137073 Thaumatotibia leucotreta Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
150000001356 alkyl thiols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
125000004369 butenyl group Chemical group C(=CCC)* 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
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000227 grinding Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000010534 nucleophilic substitution reaction Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000017448 oviposition Effects 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
125000004344 phenylpropyl group Chemical group 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000344 soap Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000002604 ultrasonography Methods 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
238000011925 1,2-addition Methods 0.000 description 1
ACYLNJHFXBMUIS-UHFFFAOYSA-N 1-(2,6-diethylphenyl)-4-propan-2-yltetrazole-5-thione Chemical compound CCC1=CC=CC(CC)=C1N1C(=S)N(C(C)C)N=N1 ACYLNJHFXBMUIS-UHFFFAOYSA-N 0.000 description 1
UQIOLQBBWTXEOF-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-5-propan-2-yloxytetrazole Chemical compound CC(C)OC1=NN=NN1C1=C(C(C)C)C=CC=C1C(C)C UQIOLQBBWTXEOF-UHFFFAOYSA-N 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical group CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
FEUFNKALUGDEMQ-UHFFFAOYSA-N 2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=O FEUFNKALUGDEMQ-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
241000934064 Acarus siro Species 0.000 description 1
241001558864 Aceria Species 0.000 description 1
241001204086 Acleris Species 0.000 description 1
241001506414 Aculus Species 0.000 description 1
241001672675 Adoxophyes Species 0.000 description 1
241000256111 Aedes <genus> Species 0.000 description 1
241001136265 Agriotes Species 0.000 description 1
241000218473 Agrotis Species 0.000 description 1
241000307865 Aleurothrixus floccosus Species 0.000 description 1
241000238679 Amblyomma Species 0.000 description 1
241001427556 Anoplura Species 0.000 description 1
241000625753 Anticarsia Species 0.000 description 1
241001414827 Aonidiella Species 0.000 description 1
241001600407 Aphis <genus> Species 0.000 description 1
241001002469 Archips Species 0.000 description 1
241001480748 Argas Species 0.000 description 1
241000384127 Argyrotaenia Species 0.000 description 1
241000387313 Aspidiotus Species 0.000 description 1
241001174347 Atomaria Species 0.000 description 1
241000726103 Atta Species 0.000 description 1
241001367049 Autographa Species 0.000 description 1
241000193388 Bacillus thuringiensis Species 0.000 description 1
241000254127 Bemisia tabaci Species 0.000 description 1
241001142392 Bibio Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000238659 Blatta Species 0.000 description 1
241000238658 Blattella Species 0.000 description 1
241001643374 Brevipalpus Species 0.000 description 1
241000398201 Bryobia praetiosa Species 0.000 description 1
241000661305 Busseola fusca Species 0.000 description 1
241000726760 Cadra cautella Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000257163 Calliphora vicina Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001347512 Carposina Species 0.000 description 1
235000014036 Castanea Nutrition 0.000 description 1
241001070941 Castanea Species 0.000 description 1
241000717851 Cephus Species 0.000 description 1
241000255580 Ceratitis <genus> Species 0.000 description 1
241001098608 Ceratophyllus Species 0.000 description 1
241001087583 Chaetocnema tibialis Species 0.000 description 1
241000426499 Chilo Species 0.000 description 1
241000359266 Chorioptes Species 0.000 description 1
241000255945 Choristoneura Species 0.000 description 1
241000668561 Chrysomphalus Species 0.000 description 1
241001414836 Cimex Species 0.000 description 1
241000098277 Cnaphalocrocis Species 0.000 description 1
241001350387 Cnephasia Species 0.000 description 1
241001479447 Coccus hesperidum Species 0.000 description 1
241001362579 Cochylis Species 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
241000689390 Coleophora Species 0.000 description 1
241001212536 Cosmopolites Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000256054 Culex <genus> Species 0.000 description 1
241000721021 Curculio Species 0.000 description 1
241000692095 Cuterebra Species 0.000 description 1
241001634817 Cydia Species 0.000 description 1
241000157278 Dacus <genus> Species 0.000 description 1
241001481695 Dermanyssus gallinae Species 0.000 description 1
241001641895 Dermestes Species 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
241000489975 Diabrotica Species 0.000 description 1
241000511318 Diprion Species 0.000 description 1
241000511320 Diprionidae Species 0.000 description 1
241000255601 Drosophila melanogaster Species 0.000 description 1
241001425477 Dysdercus Species 0.000 description 1
241000241133 Earias Species 0.000 description 1
241000995023 Empoasca Species 0.000 description 1
241000488563 Eotetranychus carpini Species 0.000 description 1
241000630736 Ephestia Species 0.000 description 1
241001301805 Epilachna Species 0.000 description 1
241001558857 Eriophyes Species 0.000 description 1
241000917109 Eriosoma Species 0.000 description 1
241001515686 Erythroneura Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241001573987 Eucosma Species 0.000 description 1
241001331999 Euproctis Species 0.000 description 1
241000515838 Eurygaster Species 0.000 description 1
241001585293 Euxoa Species 0.000 description 1
241000371383 Fannia Species 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
241000189565 Frankliniella Species 0.000 description 1
241001660203 Gasterophilus Species 0.000 description 1
241000291751 Gilpinia polytoma Species 0.000 description 1
241000257324 Glossina <genus> Species 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
241001150406 Grapholita Species 0.000 description 1
241001243091 Gryllotalpa Species 0.000 description 1
241000790933 Haematopinus Species 0.000 description 1
241001201676 Hedya nubiferana Species 0.000 description 1
241000256257 Heliothis Species 0.000 description 1
241001659689 Hercinothrips Species 0.000 description 1
241001466007 Heteroptera Species 0.000 description 1
241001417351 Hoplocampa Species 0.000 description 1
241001480803 Hyalomma Species 0.000 description 1
241001531327 Hyphantria cunea Species 0.000 description 1
241000257176 Hypoderma <fly> Species 0.000 description 1
241001495069 Ischnocera Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
241000238681 Ixodes Species 0.000 description 1
241000400431 Keiferia lycopersicella Species 0.000 description 1
241001470016 Laodelphax Species 0.000 description 1
241000256686 Lasius <genus> Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000669027 Lepidosaphes Species 0.000 description 1
241000500881 Lepisma Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241000661345 Leptocorisa Species 0.000 description 1
241001578972 Leucoptera malifoliella Species 0.000 description 1
239000004117 Lignosulphonate Substances 0.000 description 1
241001113970 Linognathus Species 0.000 description 1
241000322707 Liposcelis Species 0.000 description 1
241000594036 Liriomyza Species 0.000 description 1
241000396080 Lissorhoptrus Species 0.000 description 1
241001261104 Lobesia botrana Species 0.000 description 1
241000254023 Locusta Species 0.000 description 1
241000257162 Lucilia <blowfly> Species 0.000 description 1
241000721696 Lymantria Species 0.000 description 1
241001190211 Lyonetia Species 0.000 description 1
241000555303 Mamestra brassicae Species 0.000 description 1
241000255908 Manduca sexta Species 0.000 description 1
240000007228 Mangifera indica Species 0.000 description 1
241000824682 Melanagromyza Species 0.000 description 1
241000254071 Melolontha Species 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
241000952627 Monomorium pharaonis Species 0.000 description 1
241000257229 Musca <genus> Species 0.000 description 1
241000721623 Myzus Species 0.000 description 1
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
241000406465 Neodiprion Species 0.000 description 1
241000359016 Nephotettix Species 0.000 description 1
241001556090 Nilaparvata Species 0.000 description 1
241001491890 Operophtera Species 0.000 description 1
241000238887 Ornithodoros Species 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
241000975417 Oscinella frit Species 0.000 description 1
241001147398 Ostrinia nubilalis Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001575015 Pammene Species 0.000 description 1
241001441428 Pandemis Species 0.000 description 1
241000486438 Panolis flammea Species 0.000 description 1
241000488585 Panonychus Species 0.000 description 1
241001450657 Parthenolecanium corni Species 0.000 description 1
241000721451 Pectinophora gossypiella Species 0.000 description 1
241000517325 Pediculus Species 0.000 description 1
241000238661 Periplaneta Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
241001439019 Phthorimaea operculella Species 0.000 description 1
241000497192 Phyllocoptruta oleivora Species 0.000 description 1
241001516577 Phylloxera Species 0.000 description 1
241000255972 Pieris <butterfly> Species 0.000 description 1
241000907661 Pieris rapae Species 0.000 description 1
241000690748 Piesma Species 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
241000193804 Planococcus <bacterium> Species 0.000 description 1
241000500437 Plutella xylostella Species 0.000 description 1
241000952063 Polyphagotarsonemus latus Species 0.000 description 1
241000254103 Popillia Species 0.000 description 1
241001201614 Prays Species 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
235000005805 Prunus cerasus Nutrition 0.000 description 1
241000668989 Pseudaulacaspis Species 0.000 description 1
241000722234 Pseudococcus Species 0.000 description 1
241001415024 Psocoptera Species 0.000 description 1
241001649229 Psoroptes Species 0.000 description 1
241000526145 Psylla Species 0.000 description 1
241001160824 Psylliodes Species 0.000 description 1
241000531582 Pulvinaria <Pelagophyceae> Species 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241001509970 Reticulitermes <genus> Species 0.000 description 1
241001136903 Rhagoletis pomonella Species 0.000 description 1
241001617044 Rhizoglyphus Species 0.000 description 1
241000722251 Rhodnius Species 0.000 description 1
241000125162 Rhopalosiphum Species 0.000 description 1
241001510236 Rhyparobia maderae Species 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
241000914334 Sahlbergella singularis Species 0.000 description 1
241001450655 Saissetia Species 0.000 description 1
241000254026 Schistocerca Species 0.000 description 1
241000722272 Schizaphis Species 0.000 description 1
241001635185 Sciara Species 0.000 description 1
241001249127 Scirpophaga Species 0.000 description 1
241000924322 Scirtothrips aurantii Species 0.000 description 1
241000893388 Scotinophara Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000931987 Sesamia Species 0.000 description 1
241000258242 Siphonaptera Species 0.000 description 1
241000180197 Sitobion Species 0.000 description 1
241000254181 Sitophilus Species 0.000 description 1
241000753143 Sitotroga Species 0.000 description 1
241001492664 Solenopsis <angiosperm> Species 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
241001341014 Sparganothis Species 0.000 description 1
241000256248 Spodoptera Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241001528589 Synanthedon Species 0.000 description 1
241000255626 Tabanus <genus> Species 0.000 description 1
241000189578 Taeniothrips Species 0.000 description 1
241000254105 Tenebrio Species 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
241001231951 Thaumetopoea Species 0.000 description 1
240000006474 Theobroma bicolor Species 0.000 description 1
241000339373 Thrips palmi Species 0.000 description 1
241000339374 Thrips tabaci Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
241000131345 Tipula <genus> Species 0.000 description 1
241001238452 Tortrix Species 0.000 description 1
241000018137 Trialeurodes vaporariorum Species 0.000 description 1
241001414833 Triatoma Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
241001259047 Trichodectes Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241000462092 Trioza erytreae Species 0.000 description 1
241000267823 Trogoderma Species 0.000 description 1
241000368303 Unaspis citri Species 0.000 description 1
235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
240000001781 Xanthosoma sagittifolium Species 0.000 description 1
241000353223 Xenopsylla cheopis Species 0.000 description 1
241001466337 Yponomeuta Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
125000005282 allenyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229940097012 bacillus thuringiensis Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
BCOZLGOHQFNXBI-UHFFFAOYSA-M benzyl-bis(2-chloroethyl)-ethylazanium;bromide Chemical compound [Br-].ClCC[N+](CC)(CCCl)CC1=CC=CC=C1 BCOZLGOHQFNXBI-UHFFFAOYSA-M 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
239000011449 brick Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 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
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
230000012173 estrus Effects 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000012447 hatching Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000036512 infertility Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 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
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
235000019357 lignosulphonate Nutrition 0.000 description 1
244000144972 livestock Species 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
150000005451 methyl sulfates Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
125000006194 pentinyl group Chemical group 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 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
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
ZVTQDOIPKNCMAR-UHFFFAOYSA-N sulfanylidene(sulfanylideneboranylsulfanyl)borane Chemical compound S=BSB=S ZVTQDOIPKNCMAR-UHFFFAOYSA-N 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
238000009736 wetting Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD90342037A 1989-06-26 1990-06-25 Thioxotetrazoline DD295632A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH236989		1989-06-26

Publications (1)

Publication Number	Publication Date
DD295632A5 true DD295632A5 (de)	1991-11-07

Family

ID=4232165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90342037A DD295632A5 (de)	1989-06-26	1990-06-25	Thioxotetrazoline

Country Status (13)

Country	Link
US (2)	US5066667A (fr)
EP (1)	EP0406163A1 (fr)
JP (1)	JPH0331270A (fr)
KR (1)	KR910000673A (fr)
CN (1)	CN1048384A (fr)
AU (1)	AU635941B2 (fr)
CA (1)	CA2019653A1 (fr)
DD (1)	DD295632A5 (fr)
IE (1)	IE902287A1 (fr)
IL (1)	IL94778A0 (fr)
PT (1)	PT94482A (fr)
ZA (1)	ZA904912B (fr)
ZW (1)	ZW10990A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994024264A1 (fr) *	1993-04-09	1994-10-27	Plant Genetic Systems N.V.	Nouvelles souches de bacille thuringiensis et leurs proteines insecticides
JP3670314B2 (ja) *	1993-08-05	2005-07-13	バイエルクロップサイエンス株式会社	１−置換−５（４ｈ）−テトラゾリノン類の製造方法
WO1996036229A1 (fr) *	1995-05-17	1996-11-21	E.I. Du Pont De Nemours And Company	Amides cycliques fongicides
US5708070A (en) *	1995-12-20	1998-01-13	Dow Corning Corporation	Silicone emulsions which crosslink by Michael addition reactions
FR2812633A1 (fr)	2000-08-04	2002-02-08	Aventis Cropscience Sa	Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides
JP4646287B2 (ja) *	2003-06-02	2011-03-09	株式会社リコー	画像形成システム、画像形成方法、画像形成プログラム、及び記録媒体
US8028969B2 (en) *	2006-08-24	2011-10-04	Stoneridge, Inc.	Valve seat and valve ball for vacuum solenoid valves
DK3013813T3 (da)	2013-06-27	2019-06-03	Pfizer	Heteroaromatiske forbindelser og anvendelse deraf som dopamin-d1-ligander
EP3560913A1 (fr)	2018-04-25	2019-10-30	Dynamit Nobel GmbH Explosivstoff- und Systemtechnik	Procédé de production de tétrazolinones

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3352678A (en) *	1962-10-05	1967-11-14	Fuji Photo Film Co Ltd	Diffusion transfer photographic materials
EP0025010B1 (fr) *	1979-07-03	1983-07-20	Ciba-Geigy Ag	Dérivés de thiourées et d'isothiourées, procédé pour leur préparation, compositions les contenant et leur utilisation comme pesticides
US4328247A (en) *	1979-09-19	1982-05-04	Ciba-Geigy Corporation	Phenoxyphenylisothioureas, production thereof and use thereof in pest control, and phenoxyphenylthioureas as intermediates for the production of the phenoxyphenylisothioureas and use thereof in pest control
IT1177105B (it) *	1983-11-04	1987-08-26	Fmc Corp	1-aril-1,4-diidro-5h-tetrazol-5-oni 4-sostituiti e relativi analoghi solforati con attivita' erbicida
IL73453A (en) *	1983-11-16	1988-02-29	Uniroyal Chem Co Inc	4-substituted-5-(thi)oxo-2-tetrazolin-1-ylalkyl phosphate derivatives and analogs,pesticidal compositions containing the same and processes for the production thereof
EP0145662B1 (fr) *	1983-12-08	1987-04-29	Ciba-Geigy Ag	Isothiourées
US4618365A (en) *	1983-12-09	1986-10-21	Uniroyal Chemical Company, Inc.	Substituted tetrazolinones and their use as herbicides
US4826529A (en) *	1983-12-09	1989-05-02	Uniroyal Chemical Company, Inc.	Substituted tetrazolinones and herbicidal compositions thereof
US4830661A (en) *	1983-12-09	1989-05-16	Uniroyal Chemical Company, Inc.	Substituted tetrazolinones and herbicidal compositions thereof
ZA869640B (en) *	1985-12-26	1987-08-26	Fmc Corp	Herbicidal 1-aryl-4-substituted-1,4-dihydro-5h-tetrazol-5-ones and sulfur analogs thereof
US4866079A (en) *	1986-03-19	1989-09-12	Ciba-Geigy Corporation	N-pyridyloxyphenylisothioureas and the use thereof in pest control
EP0256985A3 (fr) *	1986-08-15	1989-11-15	Ciba-Geigy Ag	Thiourées, isothiourées et carbodiimides substituées
US4885025A (en) *	1986-12-23	1989-12-05	Fmc Corporation	Herbicidal tetrazolinones and use thereof
US4965389A (en) *	1987-03-10	1990-10-23	Ciba-Geigy Corporation	Phenoxyphenylthioureas phenoxyphenylisothioureas and phenoxyphenylcarbodiimides and use thereof for controlling pests
US4897424A (en) *	1987-06-18	1990-01-30	Ciba-Geigy Corporation	Aryloxyphenylthioureas, aryloxyphenylisothioureas and aryloxyphenylcarbodiimides and pesticidal compositions containing them
EG18799A (en) *	1987-08-20	1994-02-28	Ciba Geigy Ag	Phenylthioureas, phenylisothioureas and phenylcarbodumides their preparation and use in the control of pests

1990
- 1990-06-18 US US07/539,755 patent/US5066667A/en not_active Expired - Fee Related
- 1990-06-19 EP EP90810445A patent/EP0406163A1/fr not_active Withdrawn
- 1990-06-19 IL IL94778A patent/IL94778A0/xx unknown
- 1990-06-22 CA CA002019653A patent/CA2019653A1/fr not_active Abandoned
- 1990-06-25 ZW ZW109/90A patent/ZW10990A1/xx unknown
- 1990-06-25 AU AU57825/90A patent/AU635941B2/en not_active Ceased
- 1990-06-25 PT PT94482A patent/PT94482A/pt not_active Application Discontinuation
- 1990-06-25 DD DD90342037A patent/DD295632A5/de not_active IP Right Cessation
- 1990-06-25 IE IE228790A patent/IE902287A1/en unknown
- 1990-06-25 ZA ZA904912A patent/ZA904912B/xx unknown
- 1990-06-25 CN CN90103118A patent/CN1048384A/zh active Pending
- 1990-06-26 JP JP2168156A patent/JPH0331270A/ja active Pending
- 1990-06-26 KR KR1019900009474A patent/KR910000673A/ko not_active Withdrawn
1991
- 1991-05-22 US US07/703,966 patent/US5138068A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2019653A1 (fr)	1990-12-26
IL94778A0 (en)	1991-04-15
KR910000673A (ko)	1991-01-30
JPH0331270A (ja)	1991-02-12
US5066667A (en)	1991-11-19
US5138068A (en)	1992-08-11
AU635941B2 (en)	1993-04-08
CN1048384A (zh)	1991-01-09
ZA904912B (en)	1991-03-27
IE902287L (en)	1990-12-26
PT94482A (pt)	1991-02-08
AU5782590A (en)	1991-01-03
IE902287A1 (en)	1991-01-16
ZW10990A1 (en)	1991-01-30
EP0406163A1 (fr)	1991-01-02

Legal Events

Date	Code	Title	Description
1996-09-26	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0483055A1 (fr)	1992-04-29	Dérivés de triazacyclohexane
EP0423072A2 (fr)	1991-04-17	Thiénylthiourées, -isothiourées et -carbodiimides
EP0530147A1 (fr)	1993-03-03	3-Cyano-2-phényl-pyrroles comme pesticides
EP0468927A2 (fr)	1992-01-29	Dérivés de carboxyméthylcyclopropane
EP0418199A2 (fr)	1991-03-20	Dérivés de guanidine
EP0467840A2 (fr)	1992-01-22	Dérivés de l'acide cyclopropyl acétique
DD295632A5 (de)	1991-11-07	Thioxotetrazoline
EP0577555B1 (fr)	1997-11-05	Dérivés d'acides carboxyliques
EP0413666B1 (fr)	1994-04-13	Dérivés de l'acide butyrique
EP0540472B1 (fr)	1997-07-09	Dérivés de l'acide butyrique, procédé pour leur préparation et leur utilisation comme pesticides
DE4207604A1 (de)	1992-09-17	Schaedlingsbekaempfungsmittel
EP0559612B1 (fr)	1996-08-14	Dérivés de dioxolane comme pesticides
EP0394191B1 (fr)	1994-02-02	Esters sulfénylés de l'acide carbamique
EP0662472B1 (fr)	1998-03-11	Dérivés d'hydrazone comme pesticides
US5077304A (en)	1991-12-31	Aminopyridines
DE69325083T2 (de)	1999-10-28	Imidazol-Derivate und ihre Verwendung als agrochemische Mittel
EP0404720B1 (fr)	1996-02-28	Agent pesticide
EP0395582A2 (fr)	1990-10-31	Bisacyléthylamines
EP0472497A1 (fr)	1992-02-26	Dérivés de l'acide thiobutyrique
DE4200742A1 (de)	1992-07-23	Iminomethylpyrazole
EP0566534A1 (fr)	1993-10-20	Dérivés du benzophénone
DE4139849A1 (de)	1992-06-11	Pyrazolylphosphorverbindungen
AU640999B2 (en)	1993-09-09	Nitroenamine derivatives
EP0507736A1 (fr)	1992-10-07	Dérivés hétérocycliques d'amidine et leur utilisation comme pesticides
DE4236126A1 (de)	1993-04-29	Cyclische buttersaeureamide