CS271471B2 - Insecticide and acaricide and method of active substances production - Google Patents

Insecticide and acaricide and method of active substances production Download PDF

Info

Publication number: CS271471B2
Authority: CS; Czechoslovakia
Prior art keywords: mortality; compounds; test; active substance; active
Prior art date: 1986-04-30

Application number

CS873075A

Other languages

Czech (cs)

English (en)

Other versions

CS307587A2 (en

Inventor

Haukur Dr Kristinsson

Odd Dr Kristiansen

Original Assignee

Ciba Geigy Ag

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.)

1986-04-30

Filing date

1987-04-30

Publication date

1990-10-12

1987-04-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1989-04-28 Priority to CS892629A priority Critical patent/CS272249B2/cs

1990-02-12 Publication of CS307587A2 publication Critical patent/CS307587A2/cs

1990-10-12 Publication of CS271471B2 publication Critical patent/CS271471B2/cs

Links

239000013543 active substance Substances 0.000 title claims description 37
230000000895 acaricidal effect Effects 0.000 title description 10
238000000034 method Methods 0.000 title description 10
239000000642 acaricide Substances 0.000 title description 6
239000002917 insecticide Substances 0.000 title description 6
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 91
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
230000000694 effects Effects 0.000 claims description 13
241000238631 Hexapoda Species 0.000 claims description 10
239000000839 emulsion Substances 0.000 claims description 9
230000000749 insecticidal effect Effects 0.000 claims description 9
241000196324 Embryophyta Species 0.000 claims description 8
241000254173 Coleoptera Species 0.000 claims description 5
241000257162 Lucilia <blowfly> Species 0.000 claims description 4
241000256250 Spodoptera littoralis Species 0.000 claims description 3
235000013601 eggs Nutrition 0.000 claims description 3
239000002609 medium Substances 0.000 claims description 3
235000015097 nutrients Nutrition 0.000 claims description 3
238000005507 spraying Methods 0.000 claims description 3
241000254175 Anthonomus grandis Species 0.000 claims description 2
241000256113 Culicidae Species 0.000 claims description 2
241000255925 Diptera Species 0.000 claims description 2
241000256257 Heliothis Species 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
239000001963 growth medium Substances 0.000 claims description 2
150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
238000009736 wetting Methods 0.000 claims description 2
240000002024 Gossypium herbaceum Species 0.000 claims 3
235000004341 Gossypium herbaceum Nutrition 0.000 claims 3
238000002474 experimental method Methods 0.000 claims 3
230000001418 larval effect Effects 0.000 claims 3
241000256118 Aedes aegypti Species 0.000 claims 2
240000001624 Espostoa lanata Species 0.000 claims 2
235000009161 Espostoa lanata Nutrition 0.000 claims 2
241001556089 Nilaparvata lugens Species 0.000 claims 2
239000007921 spray Substances 0.000 claims 2
241001480736 Amblyomma hebraeum Species 0.000 claims 1
241000238678 Boophilus Species 0.000 claims 1
241000256244 Heliothis virescens Species 0.000 claims 1
241000219745 Lupinus Species 0.000 claims 1
206010030113 Oedema Diseases 0.000 claims 1
241001494479 Pecora Species 0.000 claims 1
238000003556 assay Methods 0.000 claims 1
244000052616 bacterial pathogen Species 0.000 claims 1
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
238000011156 evaluation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000009246 food effect Effects 0.000 claims 1
230000002940 repellent Effects 0.000 claims 1
239000005871 repellent Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 26
-1 n-pentane Chemical class 0.000 description 21
150000003839 salts Chemical class 0.000 description 21
239000004480 active ingredient Substances 0.000 description 20
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 13
239000002253 acid Substances 0.000 description 12
125000000217 alkyl group Chemical group 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000004094 surface-active agent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
239000008187 granular material Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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 6
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 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000758 substrate Substances 0.000 description 5
OYUQCQCQLDTRHQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbonitrile Chemical class NC1=NC=C(C#N)C(N)=N1 OYUQCQCQLDTRHQ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
101150046432 Tril gene Proteins 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
244000078703 ectoparasite Species 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
230000012447 hatching Effects 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000000087 stabilizing effect Effects 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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 2
SXQHZMRZFJYJLZ-UHFFFAOYSA-N 4-amino-2-(cyclopropylamino)-6-methylsulfanylpyrimidine-5-carbonitrile Chemical compound NC1=C(C#N)C(SC)=NC(NC2CC2)=N1 SXQHZMRZFJYJLZ-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
241000258916 Leptinotarsa decemlineata Species 0.000 description 2
235000019738 Limestone Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=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
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
244000038559 crop plants Species 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
239000000428 dust Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000006028 limestone Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000007774 longterm Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
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 2
230000000361 pesticidal effect Effects 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003230 pyrimidines Chemical class 0.000 description 2
239000000344 soap Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
UFTQNUPCWCNPQM-UHFFFAOYSA-N (2,2-dicyano-1-methylsulfanylethenyl)cyanamide;sodium Chemical compound [Na].N#CNC(SC)=C(C#N)C#N UFTQNUPCWCNPQM-UHFFFAOYSA-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
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
DNFKIFHUNIYLJR-UHFFFAOYSA-N 2,4-diamino-6-(cyclopropylamino)pyridine-3-carbonitrile Chemical compound NC1=CC(=NC(=C1C#N)N)NC1CC1 DNFKIFHUNIYLJR-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SAAAZRCMNWJXEG-UHFFFAOYSA-N 4-amino-2-(diethylamino)-6-methylsulfanylpyrimidine-5-carbonitrile Chemical compound CCN(CC)C1=NC(N)=C(C#N)C(SC)=N1 SAAAZRCMNWJXEG-UHFFFAOYSA-N 0.000 description 1
HIDNEKNSSRHLPC-UHFFFAOYSA-N 4-amino-2-(diethylamino)-6-methylsulfonylpyrimidine-5-carbonitrile Chemical compound CCN(CC)C1=NC(N)=C(C#N)C(S(C)(=O)=O)=N1 HIDNEKNSSRHLPC-UHFFFAOYSA-N 0.000 description 1
150000005007 4-aminopyrimidines Chemical class 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
IFMCROIMZMUGRF-UHFFFAOYSA-N 5-nitropyrimidine-2,4,6-triamine Chemical class NC1=NC(N)=C([N+]([O-])=O)C(N)=N1 IFMCROIMZMUGRF-UHFFFAOYSA-N 0.000 description 1
GKXYINDEGMVTOE-UHFFFAOYSA-N 6-methyl-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carbonitrile Chemical compound CC=1NC(=S)NC(=O)C=1C#N GKXYINDEGMVTOE-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241001427556 Anoplura Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241001416092 Buteo buteo Species 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241001635274 Cydia pomonella Species 0.000 description 1
241001481702 Dermanyssidae Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
241000258937 Hemiptera Species 0.000 description 1
NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
241001466007 Heteroptera Species 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
241001495069 Ischnocera Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000736227 Lucilia sericata Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
239000004743 Polypropylene Chemical class 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241001415024 Psocoptera Species 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000258242 Siphonaptera Species 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
239000004147 Sorbitan trioleate Substances 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940091181 aconitic acid Drugs 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
239000011449 brick Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003093 cationic surfactant Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000003599 detergent Substances 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-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
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000005452 ethyl sulfates Chemical class 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
235000013305 food Nutrition 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
235000019253 formic acid Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
230000000974 larvacidal effect Effects 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
244000144972 livestock Species 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
150000005451 methyl sulfates Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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 class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000017448 oviposition Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000009304 pastoral farming Methods 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
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
150000003021 phthalic acid derivatives Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001155 polypropylene Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 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
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Chemical class 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-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
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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
- A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
- Y10T428/31649—Ester, halide or nitrile of addition polymer
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Insects & Arthropods (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS873075A 1986-04-30 1987-04-30 Insecticide and acaricide and method of active substances production CS271471B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS892629A CS272249B2 (en)	1986-04-30	1989-04-28	Method of new substituted 2,4-diamino-5-cyanopirimidines production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH177286		1986-04-30

Publications (2)

Publication Number	Publication Date
CS307587A2 CS307587A2 (en)	1990-02-12
CS271471B2 true CS271471B2 (en)	1990-10-12

Family

ID=4218235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS873075A CS271471B2 (en)	1986-04-30	1987-04-30	Insecticide and acaricide and method of active substances production

Country Status (26)

Country	Link
US (1)	US4783468A (es)
EP (1)	EP0244360B1 (es)
JP (1)	JPH0688981B2 (es)
KR (1)	KR870010011A (es)
CN (1)	CN87103168A (es)
AR (1)	AR247389A1 (es)
AT (1)	ATE79614T1 (es)
AU (1)	AU598254B2 (es)
BR (1)	BR8702106A (es)
CA (1)	CA1292231C (es)
CS (1)	CS271471B2 (es)
DD (1)	DD270907A5 (es)
DE (1)	DE3781196D1 (es)
DK (3)	DK165690C (es)
ES (1)	ES2051771T3 (es)
GR (1)	GR3005856T3 (es)
HK (1)	HK11694A (es)
HU (3)	HU204396B (es)
IL (1)	IL82343A0 (es)
NZ (1)	NZ220132A (es)
PH (1)	PH24337A (es)
PT (1)	PT84774B (es)
SG (1)	SG135993G (es)
SU (2)	SU1657061A3 (es)
TR (1)	TR22942A (es)
ZA (1)	ZA873082B (es)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2941794A (en) *	1956-04-13	1960-06-21	Geddes Edith Bel	Building structures
EP0508353B1 (de) *	1991-04-11	1996-06-26	Lonza Ag	Verfahren zur Herstellung von 4-Amino-2-chlor-5-cyan-6-(methylthio)pyrimidin
RU95113597A (ru) *	1992-12-02	1997-06-10	ФМК Корпорейшн (US)	Инсектицидная композиция, способы борьбы с насекомыми
US5344955A (en) *	1993-02-19	1994-09-06	Ciba-Geigy Corporation	Preparation of 1-amino-cyan-amido-2,2-dicyanoethylene, sodium salt
DE4311901A1 (de) *	1993-04-10	1994-10-13	Huels Chemische Werke Ag	Neue Azeomethine, ein Verfahren zu ihrer Herstellung sowie deren Verwendung
WO1995003282A2 (en) *	1993-07-26	1995-02-02	Ciba-Geigy Ag	Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines
TR199802183T2 (en) *	1996-04-29	2002-06-21	Novartis Ag	B�cek �ld�r�c� bile�im.
DK1007516T3 (da) *	1997-08-27	2004-10-18	Novartis Ag	Dicyclanylpolymorfe og hydrater og fremstilling deraf
AU2007202548B1 (en) *	2007-06-01	2007-11-01	Zoetis Services Llc	Pesticide Composition
WO2009118312A1 (en) *	2008-03-28	2009-10-01	Novartis Ag	Dicyclanil formulation
AU2010201828A1 (en) *	2009-05-08	2010-11-25	Jurox Pty Ltd	Veterinary composition
WO2011035288A1 (en)	2009-09-21	2011-03-24	Merial Limited	Dicyclanil-based aqueous suspension and non-aqueous solution pour-on and spray on formulations for the prevention and treatment of insect infestation in animal
CN102113496B (zh) *	2010-01-03	2013-04-03	海利尔药业集团股份有限公司	一种含有环虫腈和灭多威的杀虫组合物
JP5731205B2 (ja) *	2011-01-14	2015-06-10	株式会社エス・ディー・エスバイオテック	農園芸用の有害生物防除剤としてのピリミジン誘導体
CN102250017A (zh) *	2011-06-15	2011-11-23	扬州天和药业有限公司	地昔尼尔的一种合成方法
CN102399193A (zh) *	2011-12-15	2012-04-04	连云港市亚晖医药化工有限公司	4,6-二氨基-2-环丙胺基-5-腈基嘧啶的制备方法
CN103416420B (zh) *	2012-05-18	2015-10-14	陕西汤普森生物科技有限公司	一种含环虫腈的杀虫组合物
CN103416430B (zh) *	2012-05-24	2016-01-13	陕西汤普森生物科技有限公司	一种农药组合物
CN103444765A (zh) *	2012-05-31	2013-12-18	陕西汤普森生物科技有限公司	一种含环虫腈与拟除虫菊酯类的杀虫组合物
JP2015003900A (ja) *	2013-05-23	2015-01-08	宮崎みどり製薬株式会社	ワクモ防除剤
CN103880759B (zh) *	2014-01-28	2016-04-20	东南大学	一种地昔尼尔药物晶型ⅰ及其制备方法
CN104130197A (zh) *	2014-07-29	2014-11-05	华中农业大学	2,4,6-三氨基-5-氰基嘧啶的化学合成方法
CN104649982B (zh) *	2015-02-26	2016-12-07	齐鲁晟华制药有限公司	一种地昔尼尔的制备方法
PL239600B1 (pl) *	2018-09-20	2021-12-20	Icb Pharma Tomasz Swietoslawski Pawel Swietoslawski Spolka Jawna	Nowa sól dicyclanilu, sposób otrzymywania takiej soli, kompozycje zawierające taką sól oraz zastosowanie takiej soli do zwalczania i kontrolowania pasożytów, a zwłaszcza larw muchówek
WO2025004000A1 (en)	2023-06-29	2025-01-02	Elanco Australasia Pty Ltd.	Formulation for controling blowfly infestations

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH376115A (de) *	1957-12-06	1964-03-31	Ciba Geigy	Verfahren zur Herstellung neuer substituierter Pyrimidine
CH574206A5 (es) *	1972-11-16	1976-04-15	Ciba Geigy Ag
GB1523274A (en) *	1974-08-05	1978-08-31	Ici Ltd	Herbicidal compositions containing substituted pyrimidine
CA1072556A (en) *	1976-08-27	1980-02-26	Fmc Corporation	Herbicidal 5-pyrimidinecarbonitriles
US4092150A (en) *	1976-08-27	1978-05-30	Fmc Corporation	Herbicidal 5-pyrimidinecarbonitriles
DD157192A1 (de) *	1981-03-13	1982-10-20	Rainer Evers	Verfahren zur synthese von 2-funktionalisierten 4-alkylthio-6-amino-pyrimidin-5-carbonitrilen
CH652396A5 (de) *	1981-12-07	1985-11-15	Ciba Geigy Ag	Amino-5-nitropyrimidin-derivate.
DE3205638A1 (de) *	1982-02-17	1983-08-25	Hoechst Ag, 6230 Frankfurt	Trisubstituierte pyrimidin-5-carbonsaeuren und deren derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel

1987
- 1987-04-22 US US07/041,163 patent/US4783468A/en not_active Expired - Lifetime
- 1987-04-24 DE DE8787810262T patent/DE3781196D1/de not_active Expired - Lifetime
- 1987-04-24 ES ES87810262T patent/ES2051771T3/es not_active Expired - Lifetime
- 1987-04-24 AT AT87810262T patent/ATE79614T1/de not_active IP Right Cessation
- 1987-04-24 EP EP87810262A patent/EP0244360B1/de not_active Expired - Lifetime
- 1987-04-27 IL IL82343A patent/IL82343A0/xx not_active IP Right Cessation
- 1987-04-28 AR AR87307408A patent/AR247389A1/es active
- 1987-04-28 CA CA000535755A patent/CA1292231C/en not_active Expired - Lifetime
- 1987-04-28 PT PT84774A patent/PT84774B/pt unknown
- 1987-04-29 ZA ZA873082A patent/ZA873082B/xx unknown
- 1987-04-29 HU HU873977A patent/HU204396B/hu not_active IP Right Cessation
- 1987-04-29 AU AU72194/87A patent/AU598254B2/en not_active Expired
- 1987-04-29 CN CN198787103168A patent/CN87103168A/zh active Pending
- 1987-04-29 NZ NZ220132A patent/NZ220132A/xx unknown
- 1987-04-29 HU HU871953A patent/HU201651B/hu unknown
- 1987-04-29 PH PH35196A patent/PH24337A/en unknown
- 1987-04-29 DD DD87302257A patent/DD270907A5/de not_active IP Right Cessation
- 1987-04-29 HU HU9203430A patent/HU9203430D0/hu unknown
- 1987-04-29 DK DK217787A patent/DK165690C/da not_active IP Right Cessation
- 1987-04-29 SU SU874202490A patent/SU1657061A3/ru active
- 1987-04-29 BR BR8702106A patent/BR8702106A/pt unknown
- 1987-04-30 KR KR870004197A patent/KR870010011A/ko not_active Application Discontinuation
- 1987-04-30 JP JP62107947A patent/JPH0688981B2/ja not_active Expired - Lifetime
- 1987-04-30 TR TR291/87A patent/TR22942A/xx unknown
- 1987-04-30 CS CS873075A patent/CS271471B2/cs unknown
1988
- 1988-06-28 SU SU884355955A patent/SU1711672A3/ru active
1992
- 1992-05-12 DK DK061792A patent/DK61792A/da not_active Application Discontinuation
- 1992-05-12 DK DK061692A patent/DK61692A/da not_active Application Discontinuation
- 1992-10-01 GR GR920401774T patent/GR3005856T3/el unknown
1993
- 1993-12-21 SG SG135993A patent/SG135993G/en unknown
1994
- 1994-02-08 HK HK116/94A patent/HK11694A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL82343A0 (en)	1987-10-30
AR247389A1 (es)	1994-12-29
JPS62263162A (ja)	1987-11-16
ATE79614T1 (de)	1992-09-15
TR22942A (tr)	1988-12-08
SU1657061A3 (ru)	1991-06-15
KR870010011A (ko)	1987-11-30
EP0244360B1 (de)	1992-08-19
SU1711672A3 (ru)	1992-02-07
CA1292231C (en)	1991-11-19
HU204396B (en)	1992-01-28
HUT44895A (en)	1988-05-30
US4783468A (en)	1988-11-08
DK61792D0 (da)	1992-05-12
DK165690C (da)	1993-05-24
DK61692D0 (da)	1992-05-12
DK217787D0 (da)	1987-04-29
GR3005856T3 (es)	1993-06-07
HUT44128A (en)	1988-02-29
PT84774A (en)	1987-05-01
DK61692A (da)	1992-05-12
DK61792A (da)	1992-05-12
HU9203430D0 (en)	1993-03-01
BR8702106A (pt)	1988-02-09
NZ220132A (en)	1990-06-26
HU903977D0 (en)	1990-11-28
CN87103168A (zh)	1987-12-16
AU7219487A (en)	1987-11-05
PT84774B (pt)	1989-12-29
HU201651B (en)	1990-12-28
ZA873082B (en)	1987-12-30
DK165690B (da)	1993-01-04
PH24337A (en)	1990-06-13
HK11694A (en)	1994-02-18
DE3781196D1 (de)	1992-09-24
AU598254B2 (en)	1990-06-21
DK217787A (da)	1987-10-31
CS307587A2 (en)	1990-02-12
DD270907A5 (de)	1989-08-16
SG135993G (en)	1994-03-31
EP0244360A2 (de)	1987-11-04
ES2051771T3 (es)	1994-07-01
EP0244360A3 (en)	1988-08-10
JPH0688981B2 (ja)	1994-11-09

Publication	Publication Date	Title
CS271471B2 (en)	1990-10-12	Insecticide and acaricide and method of active substances production
KR0124933B1 (ko)	1997-12-08	치환된 n-피리딜메틸-n'-시아노구아니딘 및 그의 제법
US4918088A (en)	1990-04-17	Pest control
JPH0347159A (ja)	1991-02-28	置換ｎ―ベンゾイル―ｎ′―２，５―ジクロロ―４―ヘキサフルオロプロピルオキシフェニル尿素の製造のための中間体
JPS6011907B2 (ja)	1985-03-28	チアゾリルケイ皮酸ニトリル、その化合物の製造方法及びその化合物を含有する農業用殺虫剤
HU212127B (en)	1996-02-28	Herbicidal compositions containing sulfonylurea derivative as active ingredient against graminaceous weeds in field of small grain cereals and use of them
KR910000252B1 (ko)	1991-01-23	해충방제에 유용한 벤조일페닐우레아의 제조방법
HU196767B (en)	1989-01-30	Process for production of derivatives of 2-/acyl-amin/-4-amin-2,4-bis /acyl-amin/-6-/alkyl-amin/-and-cycloalkyl-amin/-1,3,5-triasinine and agrochemical larvicides containg these compounds as active substance
JPH0637455B2 (ja)	1994-05-18	フェノキシフェニルチオ尿素、フェノキシフェニルイソチオ尿素およびフェノキシフェニルカルボジイミド、それらの中間体および製法
US4559353A (en)	1985-12-17	Insecticidally active 2,6-disubstituted benzimidate derivatives
JPS6293268A (ja)	1987-04-28	置換ｎ−ベンゾイル−ｎ′−３，５−ジクロロ−４−ヘキサフルオロプロピルオキシフエニル尿素及びその製造方法
JPS6165859A (ja)	1986-04-04	Ｎ‐〔３‐ハロ‐４‐（ヘキサフルオロプロポキシ）‐５‐トリフルオロメチル〕フエニル‐ｎ′‐ベンゾイルウレア、その製造方法、それらを含有する有害生物防除剤、及びその使用方法
KR960010344B1 (ko)	1996-07-30	치환된 2,4-디아미노-5-시아노피리미딘 및 이들 화합물의 제조방법
KR0150400B1 (ko)	1998-10-15	치환된 2,4-디아미노-5-시아노피리미딘 및 이들 화합물의 제조방법
JPS63179864A (ja)	1988-07-23	新規なジヒドロチアジアゾール及びこれを含有する有害生物防除剤
US4567190A (en)	1986-01-28	Pesticidal phenylhydrazonopyrrolidines
JPS6084250A (ja)	1985-05-13	しゆう酸アニリド、その製造方法及び有害生物を防除するためのその使用方法
JPS61155370A (ja)	1986-07-15	新規ｎ−ベンゾイル−ｎ′−ピリジルオキシフェニル尿素、それら製造法およびそれらからなる有害生物防除剤
GB2144412A (en)	1985-03-06	Substituted phenylhydrazonopyrrolidine derivatives and their use in pesticide compositions
JPS61109781A (ja)	1986-05-28	オキサジアジン、その製法並びに該化合物を合有する有害生物防除用組成物
JPS6115879A (ja)	1986-01-23	新規なｎ‐フエニル‐ｎ‐テトラヒドロピラニル‐ｎ‐ベンゾイル尿素、その製法及び該化合物を含有する有害生物防除剤
PL151683B1 (en)	1990-09-28	Insecticide and/or acaricide
JPS5910581A (ja)	1984-01-20	ベンゾイルパラバン酸、その製法および有害生物防除用組成物
JPS62106069A (ja)	1987-05-16	新規なベンゾイル尿素の塩、その製造方法及び有害生物防除方法
JPH0225458A (ja)	1990-01-26	ベンゾイルフェニル尿素