CS205135B2 - Method of making the n-phenyl-n'-/2-chlor-6-fluorbenzyl/-urea - Google Patents
Method of making the n-phenyl-n'-/2-chlor-6-fluorbenzyl/-urea Download PDFInfo
- Publication number
- CS205135B2 CS205135B2 CS796220A CS622079A CS205135B2 CS 205135 B2 CS205135 B2 CS 205135B2 CS 796220 A CS796220 A CS 796220A CS 622079 A CS622079 A CS 622079A CS 205135 B2 CS205135 B2 CS 205135B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chloro
- phenyl
- urea
- trifluoromethyl
- fluorbenzyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000004202 carbamide Substances 0.000 title 1
- -1 2-chloro-6-fluorobenzoyl Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- KLOZZZNFJYMTNE-UHFFFAOYSA-N 2-chloro-6-fluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1Cl KLOZZZNFJYMTNE-UHFFFAOYSA-N 0.000 claims description 6
- 235000013877 carbamide Nutrition 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IHHUGFJSEJSCGE-UHFFFAOYSA-N 1-isocyanato-2-phenylbenzene Chemical compound O=C=NC1=CC=CC=C1C1=CC=CC=C1 IHHUGFJSEJSCGE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QWXAYHAPQNMAKI-UHFFFAOYSA-N 2-chloro-4-isocyanato-1-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(N=C=O)C=C1Cl QWXAYHAPQNMAKI-UHFFFAOYSA-N 0.000 description 1
- UQXQIGFHOXLSOB-UHFFFAOYSA-N 2-chloro-6-fluoro-n-(phenylcarbamoyl)benzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC1=CC=CC=C1 UQXQIGFHOXLSOB-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782801316 DE2801316A1 (de) | 1978-01-13 | 1978-01-13 | Substituierte n-phenyl-n'-(2-chlor- 6-fluor-benzoyl)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
Publications (1)
Publication Number | Publication Date |
---|---|
CS205135B2 true CS205135B2 (en) | 1981-04-30 |
Family
ID=6029415
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS79203A CS205134B2 (en) | 1978-01-13 | 1979-01-09 | Insecticide means and method of making the active substances |
CS796220A CS205135B2 (en) | 1978-01-13 | 1979-01-09 | Method of making the n-phenyl-n'-/2-chlor-6-fluorbenzyl/-urea |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS79203A CS205134B2 (en) | 1978-01-13 | 1979-01-09 | Insecticide means and method of making the active substances |
Country Status (27)
Country | Link |
---|---|
US (1) | US4277499A (no) |
EP (1) | EP0003099B1 (no) |
JP (1) | JPS54100344A (no) |
AR (1) | AR223164A1 (no) |
AT (1) | AT363724B (no) |
AU (1) | AU518182B2 (no) |
BR (1) | BR7900196A (no) |
CA (1) | CA1095932A (no) |
CS (2) | CS205134B2 (no) |
DD (2) | DD141406A5 (no) |
DE (2) | DE2801316A1 (no) |
DK (1) | DK149448C (no) |
EG (1) | EG13734A (no) |
ES (1) | ES476796A1 (no) |
FI (1) | FI63392C (no) |
GR (1) | GR73087B (no) |
HU (1) | HU181405B (no) |
IL (1) | IL56405A (no) |
NO (1) | NO149386C (no) |
NZ (1) | NZ189349A (no) |
OA (1) | OA06146A (no) |
PH (1) | PH13875A (no) |
PL (2) | PL120284B1 (no) |
PT (1) | PT69039A (no) |
RO (1) | RO75588A (no) |
TR (1) | TR20429A (no) |
ZA (1) | ZA79145B (no) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5245071A (en) * | 1970-05-15 | 1993-09-14 | Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
US5342958A (en) * | 1970-05-15 | 1994-08-30 | Solvay Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
USRE32418E (en) * | 1977-05-13 | 1987-05-12 | The Dow Chemical Company | Substituted(((phenyl)amino)carbonyl)-benzamides |
DE2919292A1 (de) * | 1979-05-12 | 1980-11-20 | Bayer Ag | Substituierte harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als pflanzenbakterizide |
US4348412A (en) | 1979-07-11 | 1982-09-07 | Ciba-Geigy Corporation | Insecticidal phenylureas and methods of use thereof |
US4399152A (en) * | 1980-04-03 | 1983-08-16 | Duphar International B.V. | Substituted benzoyl ureas as insecticides |
DK172687B1 (da) * | 1981-07-30 | 1999-05-31 | Dow Agrosciences Llc | Substituerede N-aroyl-N'-phenyl-urinstofforbindelser, mellemprodukt til brug ved fremstilling deraf, en fremgangsmåde til d |
US4431667A (en) * | 1981-12-04 | 1984-02-14 | The Upjohn Company | Imino ethers useful for controlling insect and arachnoid pests |
US4438110A (en) | 1982-04-28 | 1984-03-20 | Union Carbide Corporation | Chewing insect toxicant compositions |
DE3217619A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,4-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
DE3217620A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,5-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
US4868215A (en) * | 1982-07-26 | 1989-09-19 | The Dow Chemical Company | Substituted N-aroyl N'-phenyl urea compounds |
JPS6092260A (ja) * | 1983-10-27 | 1985-05-23 | Nippon Tokushu Noyaku Seizo Kk | 新規アニリン誘導体 |
US4659736A (en) * | 1984-01-21 | 1987-04-21 | Bayer Aktiengesellschaft | Benzoyl urea compounds as agents for repelling snails and slugs |
JPS60181067A (ja) * | 1984-02-27 | 1985-09-14 | Takeda Chem Ind Ltd | ベンゾイル尿素誘導体,その製造法及び殺虫剤 |
JPS60181063A (ja) * | 1984-02-27 | 1985-09-14 | Takeda Chem Ind Ltd | ベンゾイル尿素誘導体、その製造法及び殺虫剤 |
TR23048A (tr) * | 1984-08-31 | 1989-02-14 | Ciba Geigy Ag | Fenilbenzoiluereler,bunlarin im aline mahsus usul ve bunlarin zararhlarla muecadelede kullanimi |
JPS6197255A (ja) * | 1984-10-18 | 1986-05-15 | チバ‐ガイギー アクチエンゲゼルシヤフト | 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、その製造方法及び該化合物を含有する組成物 |
DE3439364A1 (de) * | 1984-10-27 | 1986-04-30 | Bayer Ag, 5090 Leverkusen | Benzoylharnstoffe und zwischenprodukte |
US5288756A (en) * | 1985-10-14 | 1994-02-22 | Ciba-Geigy Corporation | Benzoylphenylureas |
EP0219460B1 (de) * | 1985-10-14 | 1991-05-02 | Ciba-Geigy Ag | Benzoylphenylharnstoffe |
DE3613062A1 (de) * | 1986-04-18 | 1987-10-29 | Hoechst Ag | N-benzoyl-n'-phenyl(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
GB8700838D0 (en) * | 1987-01-15 | 1987-02-18 | Shell Int Research | Termiticides |
JP2661709B2 (ja) * | 1988-07-08 | 1997-10-08 | ダウ・ケミカル日本株式会社 | 高活性な農薬水和剤の製法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4013717A (en) * | 1970-05-15 | 1977-03-22 | U.S. Philips Corporation | Benzoyl phenyl urea derivatives having insecticidal activities |
DE2531279C2 (de) * | 1975-07-12 | 1983-07-14 | Bayer Ag, 5090 Leverkusen | N-(3-Trifluormethyl-4-halogen-phenyl)- N'-benzoyl-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
DE2601780B2 (de) * | 1976-01-20 | 1979-07-26 | Bayer Ag, 5090 Leverkusen | N-Phenyl-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
US4089975A (en) * | 1977-05-13 | 1978-05-16 | The Dow Chemical Company | Method of controlling manure-breeding insects |
US4170657A (en) * | 1977-05-13 | 1979-10-09 | The Dow Chemical Company | Substituted(((phenyl)amino)carbonyl)-benzamides |
-
1978
- 1978-01-13 DE DE19782801316 patent/DE2801316A1/de not_active Withdrawn
- 1978-12-29 NO NO784421A patent/NO149386C/no unknown
-
1979
- 1979-01-02 DE DE7979100005T patent/DE2960791D1/de not_active Expired
- 1979-01-02 EP EP79100005A patent/EP0003099B1/de not_active Expired
- 1979-01-05 PT PT69039A patent/PT69039A/pt unknown
- 1979-01-09 CS CS79203A patent/CS205134B2/cs unknown
- 1979-01-09 CS CS796220A patent/CS205135B2/cs unknown
- 1979-01-10 NZ NZ189349A patent/NZ189349A/xx unknown
- 1979-01-10 RO RO7996239A patent/RO75588A/ro unknown
- 1979-01-10 IL IL56405A patent/IL56405A/xx unknown
- 1979-01-10 EG EG15/79A patent/EG13734A/xx active
- 1979-01-11 TR TR20429A patent/TR20429A/xx unknown
- 1979-01-11 FI FI790087A patent/FI63392C/fi not_active IP Right Cessation
- 1979-01-11 DD DD79210441A patent/DD141406A5/de unknown
- 1979-01-11 JP JP105779A patent/JPS54100344A/ja active Granted
- 1979-01-11 DD DD79218771A patent/DD148771A5/de unknown
- 1979-01-12 DK DK13779A patent/DK149448C/da not_active IP Right Cessation
- 1979-01-12 CA CA319,597A patent/CA1095932A/en not_active Expired
- 1979-01-12 ZA ZA79145A patent/ZA79145B/xx unknown
- 1979-01-12 HU HU79BA3747A patent/HU181405B/hu unknown
- 1979-01-12 AR AR275153A patent/AR223164A1/es active
- 1979-01-12 PL PL1979219740A patent/PL120284B1/pl unknown
- 1979-01-12 PH PH22058A patent/PH13875A/en unknown
- 1979-01-12 AU AU43340/79A patent/AU518182B2/en not_active Ceased
- 1979-01-12 AT AT0023879A patent/AT363724B/de not_active IP Right Cessation
- 1979-01-12 OA OA56705A patent/OA06146A/xx unknown
- 1979-01-12 ES ES476796A patent/ES476796A1/es not_active Expired
- 1979-01-12 PL PL1979212760A patent/PL116480B1/pl unknown
- 1979-01-12 BR BR7900196A patent/BR7900196A/pt unknown
- 1979-01-12 GR GR58073A patent/GR73087B/el unknown
-
1980
- 1980-02-01 US US06/117,755 patent/US4277499A/en not_active Expired - Lifetime
Also Published As
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CS205135B2 (en) | Method of making the n-phenyl-n'-/2-chlor-6-fluorbenzyl/-urea | |
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