CA1042448A - Phenyl carbamates - Google Patents

Phenyl carbamates

Info

Publication number: CA1042448A
Authority: CA; Canada
Prior art keywords: formula; compound according; parts; compound; represent
Prior art date: 1973-12-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA215,912A

Other languages

English (en)

French (fr)

Other versions

CA215912S (en

Inventor

Manfred Boger

Jozef Drabek

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

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.)

1973-12-14

Filing date

1974-12-12

Publication date

1978-11-14

1973-12-14 Priority claimed from CH1745173A external-priority patent/CH586508A5/de

1974-12-12 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1978-11-14 Application granted granted Critical

1978-11-14 Publication of CA1042448A publication Critical patent/CA1042448A/en

Status Expired legal-status Critical Current

Links

BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 title claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 10
239000000460 chlorine Substances 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
241000607479 Yersinia pestis Species 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 6
241000238660 Blattidae Species 0.000 claims description 3
241001124134 Chrysomelidae Species 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
241000238631 Hexapoda Species 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
241000238876 Acari Species 0.000 claims 1
241000500891 Insecta Species 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
239000013543 active substance Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
241000258916 Leptinotarsa decemlineata Species 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
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 5
239000000843 powder Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
-1 Cl-C4-alkyl Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000000839 emulsion Substances 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
239000007787 solid Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
241000238662 Blatta orientalis Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000238675 Periplaneta americana Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
125000000913 palmityl 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])C([H])([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 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
QFBDCSDDHUBEGG-UHFFFAOYSA-N 1,2-dibutylnaphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 QFBDCSDDHUBEGG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 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
229940115440 aluminum sodium silicate Drugs 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other 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
- 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

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

CA215,912A 1973-12-14 1974-12-12 Phenyl carbamates Expired CA1042448A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1745173A CH586508A5 (en)	1973-12-14	1973-12-14	2-Formylphenyl-N-methyl-N-phenylthio-carbamate acetals - with insecticidal and acaricidal activity
CH1524574		1974-11-15

Publications (1)

Publication Number	Publication Date
CA1042448A true CA1042448A (en)	1978-11-14

Family

ID=25715977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA215,912A Expired CA1042448A (en)	1973-12-14	1974-12-12	Phenyl carbamates

Country Status (15)

Country	Link
JP (1)	JPS5094131A (de)
AT (1)	AT335798B (de)
AU (1)	AU7638774A (de)
CA (1)	CA1042448A (de)
DE (1)	DE2458689A1 (de)
DK (1)	DK614474A (de)
ES (1)	ES432875A1 (de)
FR (1)	FR2254563B1 (de)
GB (1)	GB1486456A (de)
IE (1)	IE41530B1 (de)
IL (1)	IL46199A (de)
IT (1)	IT1049337B (de)
LU (1)	LU71468A1 (de)
NL (1)	NL7416143A (de)
SE (1)	SE7414929L (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2162527C1 (ru) *	1999-09-09	2001-01-27	Михайлов Борис Дмитриевич	Роторно-поршневой двигатель внутреннего сгорания

1974
- 1974-11-26 DK DK614474A patent/DK614474A/da unknown
- 1974-11-28 SE SE7414929A patent/SE7414929L/xx not_active Application Discontinuation
- 1974-12-06 IL IL46199A patent/IL46199A/en unknown
- 1974-12-11 DE DE19742458689 patent/DE2458689A1/de not_active Withdrawn
- 1974-12-11 FR FR7440784A patent/FR2254563B1/fr not_active Expired
- 1974-12-11 NL NL7416143A patent/NL7416143A/xx not_active Application Discontinuation
- 1974-12-12 LU LU71468A patent/LU71468A1/xx unknown
- 1974-12-12 CA CA215,912A patent/CA1042448A/en not_active Expired
- 1974-12-13 ES ES432875A patent/ES432875A1/es not_active Expired
- 1974-12-13 AT AT997474A patent/AT335798B/de not_active IP Right Cessation
- 1974-12-13 IE IE2572/74A patent/IE41530B1/en unknown
- 1974-12-13 GB GB54058/74A patent/GB1486456A/en not_active Expired
- 1974-12-13 AU AU76387/74A patent/AU7638774A/en not_active Expired
- 1974-12-13 JP JP49144009A patent/JPS5094131A/ja active Pending
- 1974-12-13 IT IT30554/74A patent/IT1049337B/it active

Also Published As

Publication number	Publication date
AU7638774A (en)	1976-06-17
IL46199A (en)	1977-05-31
GB1486456A (en)	1977-09-21
NL7416143A (nl)	1975-06-17
IT1049337B (it)	1981-01-20
IE41530L (en)	1975-06-14
FR2254563B1 (de)	1978-02-24
IL46199A0 (en)	1975-03-13
IE41530B1 (en)	1980-01-30
ES432875A1 (es)	1977-02-16
SE7414929L (sv)	1975-06-16
DE2458689A1 (de)	1975-06-19
LU71468A1 (de)	1975-08-20
JPS5094131A (de)	1975-07-26
DK614474A (de)	1975-08-11
ATA997474A (de)	1976-07-15
AT335798B (de)	1977-03-25
FR2254563A1 (de)	1975-07-11

Publication	Publication Date	Title
US4004031A (en)	1977-01-18	Bis-(O-1-alkylthio-ethylimino)-N-methyl-carbamic acid)-N,N'-sulphide insecticides
EP0012428B1 (de)	1981-05-13	Substituierte Cyanamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0120037A1 (de)	1984-10-03	Arthropodische verbindungen
CS196508B1 (en)	1980-03-31	Fungicide,insecticide,nematocide and/or herbicide
CA1042448A (en)	1978-11-14	Phenyl carbamates
JPS5925789B2 (ja)	1984-06-21	チアゾリリデン−オキソ−プロピオニトリル、その製造法並びに該化合物を含有する殺虫剤
US4017638A (en)	1977-04-12	Iso-(thio)-urea derivatives
EP0068260A2 (de)	1983-01-05	Substituierte Phenoxypropionate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE3015090A1 (de)	1981-10-22	]-(trihalogenmethyl-sulfenyl)-4-aryl-1,2,4-triazolidin-5-one, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit diesen verbindungen
CA1108140A (en)	1981-09-01	4-alkyl- and 4-allyl-mercapto-, -sulfinyl- and - sulfonyl-methyl-2-amino-6-n,n-dimethylcarbamoyloxy- pyrimidines, processes for producing them, compositions containing these pyrimidines, and the use thereof for controlling insect pests
CA1069921A (en)	1980-01-15	Esters
US4027033A (en)	1977-05-31	Pesticides
DE2156447A1 (de)	1972-06-29	Neue Amidothionophosphonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
US3326751A (en)	1967-06-20	Pesticidal compositions and methods
CA1080743A (en)	1980-07-01	Spiroheptenyl carboxylate
CA1072968A (en)	1980-03-04	Phenylcarbamate
US4064263A (en)	1977-12-20	4,5-Benzospiro(2,4)-heptane (and hepta-4,6-diene)-1-carboxylic acid esters and compositions containing same
US4034104A (en)	1977-07-05	Carbamic acid esters of gallic acid, their esters, and heavy metal salts
EP0291809B1 (de)	1992-01-15	2-Anilino-chinoline, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide
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