CS199213B2 - Insecticide and method of producing active ingredient - Google Patents

Insecticide and method of producing active ingredient Download PDF

Info

Publication number: CS199213B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compounds; active ingredient; dimethyl; bis
Prior art date: 1977-07-01

Application number

CS784303A

Other languages

Czech (cs)

English (en)

Inventor

Richard F Sauers

Original Assignee

Du Pont

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.)

1977-07-01

Filing date

1978-06-29

Publication date

1980-07-31

1978-03-10 Priority claimed from US05/885,251 external-priority patent/US4160034A/en

1978-06-29 Application filed by Du Pont filed Critical Du Pont

1980-07-31 Publication of CS199213B2 publication Critical patent/CS199213B2/cs

Links

239000004480 active ingredient Substances 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 12
239000002917 insecticide Substances 0.000 title abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 28
-1 methylimino Chemical group 0.000 claims abstract description 22
150000004657 carbamic acid derivatives Chemical class 0.000 claims abstract description 16
241000238631 Hexapoda Species 0.000 claims abstract description 15
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims abstract description 13
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 34
230000000749 insecticidal effect Effects 0.000 claims description 27
241000607479 Yersinia pestis Species 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 6
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
241000254173 Coleoptera Species 0.000 abstract description 3
241000255925 Diptera Species 0.000 abstract description 3
241000255777 Lepidoptera Species 0.000 abstract description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000004094 surface-active agent Substances 0.000 description 12
241000196324 Embryophyta Species 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000000428 dust Substances 0.000 description 6
239000008188 pellet Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
238000005507 spraying Methods 0.000 description 5
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 4
239000005916 Methomyl Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
241001521235 Spodoptera eridania Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000005054 agglomeration Methods 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
229960000892 attapulgite Drugs 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012530 fluid Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
229910052740 iodine Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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229910052625 palygorskite Inorganic materials 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
LWGRPXZKPVYNBS-UHFFFAOYSA-N 2-chlorosulfanylethyl thiohypochlorite Chemical compound ClSCCSCl LWGRPXZKPVYNBS-UHFFFAOYSA-N 0.000 description 2
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
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DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
235000020030 perry Nutrition 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000008654 plant damage Effects 0.000 description 2
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
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231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 1
OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
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239000001692 EU approved anti-caking agent Substances 0.000 description 1
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HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
LNJKJGKOBJFJIB-UHFFFAOYSA-N methyl 2-(methylcarbamoyloxy)ethanimidothioate Chemical compound CNC(=O)OCC(=N)SC LNJKJGKOBJFJIB-UHFFFAOYSA-N 0.000 description 1
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
GYGAZRPDUOHMAF-KHPPLWFESA-N oleyl acetate Chemical class CCCCCCCC\C=C/CCCCCCCCOC(C)=O GYGAZRPDUOHMAF-KHPPLWFESA-N 0.000 description 1
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229960003536 phenothrin Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
DQIGGFPVKGZBQQ-UHFFFAOYSA-N s-carbamoyl carbamothioate Chemical class NC(=O)SC(N)=O DQIGGFPVKGZBQQ-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229910002029 synthetic silica gel Inorganic materials 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS784303A 1977-07-01 1978-06-29 Insecticide and method of producing active ingredient CS199213B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81231677A	1977-07-01	1977-07-01
US05/885,251 US4160034A (en)	1977-07-01	1978-03-10	Substituted carbamates

Publications (1)

Publication Number	Publication Date
CS199213B2 true CS199213B2 (en)	1980-07-31

Family

ID=27123592

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS784303A CS199213B2 (en)	1977-07-01	1978-06-29	Insecticide and method of producing active ingredient

Country Status (22)

Country	Link
EP (1)	EP0000283B1 (tr)
JP (1)	JPS5444614A (tr)
AR (1)	AR220138A1 (tr)
AU (1)	AU515983B2 (tr)
BR (1)	BR7804185A (tr)
CA (1)	CA1107292A (tr)
CS (1)	CS199213B2 (tr)
DE (1)	DE2861154D1 (tr)
DK (1)	DK254378A (tr)
EG (1)	EG13741A (tr)
ES (1)	ES471280A1 (tr)
GB (1)	GB2001628B (tr)
GR (1)	GR64548B (tr)
IE (1)	IE47205B1 (tr)
IL (1)	IL55050A (tr)
IT (1)	IT1158872B (tr)
MX (1)	MX5138E (tr)
OA (1)	OA05999A (tr)
PH (1)	PH13803A (tr)
PL (1)	PL114208B1 (tr)
TR (1)	TR19962A (tr)
YU (1)	YU154178A (tr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR8104086A (pt) *	1980-07-03	1982-03-16	Du Pont	Processo para o controle de carrapatos

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3856972A (en) *	1970-09-24	1974-12-24	M Hirano	Carbamate pesticides

1978
- 1978-06-08 DK DK254378A patent/DK254378A/da not_active Application Discontinuation
- 1978-06-23 PH PH21318A patent/PH13803A/en unknown
- 1978-06-28 TR TR19962A patent/TR19962A/tr unknown
- 1978-06-28 EP EP78300097A patent/EP0000283B1/en not_active Expired
- 1978-06-28 AU AU37526/78A patent/AU515983B2/en not_active Expired
- 1978-06-28 GB GB787828116A patent/GB2001628B/en not_active Expired
- 1978-06-28 DE DE7878300097T patent/DE2861154D1/de not_active Expired
- 1978-06-28 MX MX787191U patent/MX5138E/es unknown
- 1978-06-28 EG EG406/78A patent/EG13741A/xx active
- 1978-06-29 ES ES471280A patent/ES471280A1/es not_active Expired
- 1978-06-29 JP JP7812978A patent/JPS5444614A/ja active Pending
- 1978-06-29 CS CS784303A patent/CS199213B2/cs unknown
- 1978-06-29 YU YU01541/78A patent/YU154178A/xx unknown
- 1978-06-30 IT IT25229/78A patent/IT1158872B/it active
- 1978-06-30 IE IE1324/78A patent/IE47205B1/en unknown
- 1978-06-30 BR BR7804185A patent/BR7804185A/pt unknown
- 1978-06-30 IL IL55050A patent/IL55050A/xx unknown
- 1978-06-30 PL PL1978208044A patent/PL114208B1/pl unknown
- 1978-06-30 GR GR56643A patent/GR64548B/el unknown
- 1978-06-30 CA CA306,631A patent/CA1107292A/en not_active Expired
- 1978-06-30 AR AR272767A patent/AR220138A1/es active
- 1978-06-30 OA OA56548A patent/OA05999A/xx unknown

Also Published As

Publication number	Publication date
IE47205B1 (en)	1984-01-11
EG13741A (en)	1982-09-30
IL55050A0 (en)	1978-08-31
IL55050A (en)	1983-03-31
YU154178A (en)	1983-01-21
GR64548B (en)	1980-04-12
AR220138A1 (es)	1980-10-15
PL208044A1 (tr)	1979-12-03
GB2001628B (en)	1982-01-13
PH13803A (en)	1980-10-01
OA05999A (fr)	1981-06-30
TR19962A (tr)	1980-05-16
ES471280A1 (es)	1979-10-01
IT7825229A0 (it)	1978-06-30
JPS5444614A (en)	1979-04-09
AU515983B2 (en)	1981-05-14
PL114208B1 (en)	1981-01-31
IT1158872B (it)	1987-02-25
DE2861154D1 (en)	1981-12-24
AU3752678A (en)	1980-01-03
EP0000283A1 (en)	1979-01-10
IE781324L (en)	1979-01-01
DK254378A (da)	1979-01-02
MX5138E (es)	1983-03-28
BR7804185A (pt)	1979-03-20
EP0000283B1 (en)	1981-10-14
CA1107292A (en)	1981-08-18
GB2001628A (en)	1979-02-07

Publication	Publication Date	Title
US3576834A (en)	1971-04-27	Substituted o-carbamylhydroxamates
US4948798A (en)	1990-08-14	Substituted cyanoiminoimidazolidines and -tetrahydropyrimidines useful as pesticides
KR900008135B1 (ko)	1990-10-31	치환된 카보디이미드의 제조방법
PL106889B1 (pl)	1980-01-31	Srodek szkodnikobojczy
CS199213B2 (en)	1980-07-31	Insecticide and method of producing active ingredient
US4225615A (en)	1980-09-30	Insecticidal and nematicidal carbamates
US4150122A (en)	1979-04-17	Substituted carbamates
US4268520A (en)	1981-05-19	Insecticidal and nematicidal carbamates
US4210668A (en)	1980-07-01	Insecticidal carbamates
EP0015745B1 (en)	1983-06-22	Pesticidal carbamoyl sulfides, and preparation and use thereof
US4160034A (en)	1979-07-03	Substituted carbamates
US4146618A (en)	1979-03-27	Substituted carbamates
US3760043A (en)	1973-09-18	O-phenyl-s-alkyl-n-alkyl-phosphoroamido-thiolates
US3824320A (en)	1974-07-16	Substituted o-carbamylhydroxamate insecticides
US4335140A (en)	1982-06-15	Insecticidal trifluoroethanimidothioate disulfides
US4291054A (en)	1981-09-22	Insecticidal carbamoyl sulfides
CA1110648A (en)	1981-10-13	Insecticidal and nematicidal carbamates
US4234592A (en)	1980-11-18	Alkylthiodiazatrithiapentalene compositions and methods of using as plant disease control agents, insecticides, and larvicides
US4316911A (en)	1982-02-23	Ureidosulfenyl carbamate nematicides
US4323578A (en)	1982-04-06	Fluorinated carbamate insecticides
US4393074A (en)	1983-07-12	Fluorinated carbamate insecticides
US4254141A (en)	1981-03-03	Insecticidal carbamoyl sulfides
EP0145328B1 (en)	1990-05-16	Substituted tetrazolinones
US4330674A (en)	1982-05-18	Carbamoyl sulfide fluorides
EP0003688B1 (en)	1982-08-04	A method of controlling mollusc pest