IL40968A - Herbicidal compositions containing 1,2-dialkyl-3,5-diaryl pyrazolium salts,some novel pyrazolium salts and process for preparing the same - Google Patents
Herbicidal compositions containing 1,2-dialkyl-3,5-diaryl pyrazolium salts,some novel pyrazolium salts and process for preparing the sameInfo
- Publication number
- IL40968A IL40968A IL40968A IL4096872A IL40968A IL 40968 A IL40968 A IL 40968A IL 40968 A IL40968 A IL 40968A IL 4096872 A IL4096872 A IL 4096872A IL 40968 A IL40968 A IL 40968A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- dimethyl
- hydrogen
- methyl
- nonionic
- Prior art date
Links
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims 8
- 230000002363 herbicidal effect Effects 0.000 title claims 4
- 239000000203 mixture Substances 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 28
- 238000000034 method Methods 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 241000196324 Embryophyta Species 0.000 claims 4
- 239000012141 concentrate Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000004094 surface-active agent Substances 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims 3
- 235000007320 Avena fatua Nutrition 0.000 claims 3
- 229940100198 alkylating agent Drugs 0.000 claims 3
- 239000002168 alkylating agent Substances 0.000 claims 3
- 125000000129 anionic group Chemical group 0.000 claims 3
- 239000003945 anionic surfactant Substances 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 3
- 239000002736 nonionic surfactant Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 244000075850 Avena orientalis Species 0.000 claims 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- -1 1 ,2-dimethyl-3- (m-methylphenyl) -5-phenylpyrazolium Chemical compound 0.000 claims 1
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 241001647031 Avena sterilis Species 0.000 claims 1
- 235000004535 Avena sterilis Nutrition 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 240000005979 Hordeum vulgare Species 0.000 claims 1
- 235000007340 Hordeum vulgare Nutrition 0.000 claims 1
- DNIZUVLEGVKXOG-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC=C1)C)C Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC=C1)C)C DNIZUVLEGVKXOG-UHFFFAOYSA-M 0.000 claims 1
- SKNBFADDWUSRNW-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC=C1)Cl)C Chemical compound S(=O)(=O)(OC)[O-].C[N+]=1N(C(=CC1C1=CC=CC=C1)C1=CC(=CC=C1)Cl)C SKNBFADDWUSRNW-UHFFFAOYSA-M 0.000 claims 1
- 235000007238 Secale cereale Nutrition 0.000 claims 1
- 244000082988 Secale cereale Species 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical group 0.000 claims 1
- 238000005349 anion exchange Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000004464 cereal grain Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000005527 methyl sulfate group Chemical group 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furnace Details (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (9)
1. A method for the control of undesirable plant species comprising applying to the foliage of said undesirable plants a herbicldally effective amount of a compound having the formula: wherein R-^ and each represent lower alkyl groups having 1 to ¾ carbon atoms; Y, Y', Z and Z' each independ- represent ently jteprasnt a member selected from the group consist- r- \ „ trifl'uoromethyl ing of hydrogen, halogen, nitro, alkyl C^-C^, haloalkyl ■C^-Cj and alkoxy C-^-C^; X represents an anion with a charge of from 1 to 3; and m is an integer selected from 1, 2 and 3.
2. A method according to Claim 1 wherein the compound has the structure wherein Y, Y', Z and Z' are hydrogen; R^ and R£ are methyl; m is 1 and X is selected from the group consisting of chloride, bromide, iodide, acetate, hydroxide, hydrogen sulfate, methyl sulfate, p_-toluene sulfonate, perchlorate and alkyl sulfonate C-^-C^ . w ., 3· A method according to Claim 1 wherein the compound is 1 , 2-dimethy 1-3 , 5-diphenylpyrazolium p_-tolu-enesulfonate . ✓ . A method according to Claim 1 wherein the compound is 1 , 2-dimethyl-3 , 5-diphenylpyrazolium methyl sulfate. 5. A method according to Claim 1 wherein the compound is 1 , 2-dimethyl-3- (m-chlorophenyl )-5-phenyl-pyrazolium methyl sulfate. - 6. A method according to Claim 1 wherein the compound is 1 , 2-dimethyl-3- (m-methylphenyl )-5-phenyl-pyrazolium methyl sulfate. 7. A method according to Claim 1 wherein the compound is l,2-dimethyl-3-(o-methylphenyl)-5-phenyl-pyrazolium methyl sulfate. 8. A method according to Claim 1 wherein the compound is 1 , 2-dimethyl-3-(p_-chlorophenyl )-5-phenyl-pyrazolium methyl sulfate. 9. A method according to Claim 1 where the undesirable plant species is wild oats and the compound has the structure wherein is methyl; is alkyl C^-C^; Y, Y', Z and Z' each independently represent a member selected from the group consisting of hydrogen, halogen, methyl and methoxy; provided that only one of the phenyl rings is substituted para to the pyrazolium ring with a substituent other than hydrogen. 10. A method according to Claim 9 wherein the compound is applied at a rate of from 0.5 to 3.0 pounds per acre. 11. A method according to Claim 9 for selectively controlling wild oats in the presence of a cereal grain crop selected from the group consisting of wheat, barley and rye by application of the compound to the wild oat infested crop. 12. A method according to Claim 11 wherein application is made by spraying an aqueous solution of ) said compound and a surfactant selected from the group consisting of nonionic; anionic and nonionic-anionic surfactants. 1
3. A method according to Claim 12 wherein the surfactant is nonionic and has a hydrophilic-lipo-philic balance of from 11 to l6. 1
4. A method according to Claim 11 wherein the compound is 1 , 2-dimethyl-3 , 5-diphenylpyrazolium methyl sulfate. 15· A method according to Claim 12 wherein the compound is 1 , 2-dimethyl-3 , 5-diphenylpyrazolium methyl sul ate. 16. A method for the preparation of a water--miscible herblcldal concentrate comprising dissolving 5$ to 70% of the compound of Claim 1 in 85% to 30$ of a water-miscible polar solvent. 17. A method according to Claim l6 further comprising the addition of a nonionic, anionic or nonionic-anionic surfactant. 18. A method according to Claim 17 wherein the compound is 1 , 2-dimethyl-3 , 5-diphenylpyrazolium methyl sulfate; the solvent is water; and the surfactant is nonionic. 19. A method according to Claim 18 wherein the nonionic surfactant has a hydrophilic-lipophilic balance of from 11 to l6. 20. A water-miscible herblcldal concentrate comprising l<¾, to 70% of a compound of Claim 1 dissolved in 85/» to 30% of water or a water-miscible polar solvent. 21. A herblcldal concentrate according to Claim 20 further comprising a nonionic, anionic or nonionic-anionic surfactant. Claim 21 wherein the compound is l,2-dimethyl-3,5--diphenylpyrazolium methyl sulfate; the solvent is water and the surfactant is a nonionic surfactant. 23. A herbicidal composition according to Claim 22 wherein the nonionic surfactant has a hydro-philic-lipophllic balance of from 11 to l6. 2k. A compound having the formula: wherein and each represent lower alkyl groups having 1 to k carbon atoms; X represents an anion with a charge of from 1 to 3; Y, Y', Z and Z' each independently represent a member selected from the group consisting of triflyoromethyl hydrogen; halogen; nitro; alkyl, C^-C^; haloalkyl , C^-C^ ; alkoxy, C-^-C^ ; and m is an integer selected from 1, 2 and 3; provided that X~m is not I-1, CIO^-1 or CI-1 when Y, Z, Y' and Z' are hydrogen and and R2 are methyl. 2
5. A compound according to Claim 2 wherein Y, Y', Z and Z' are hydrogen; R^ and are methyl; m is 1 and X is selected from the group consisting of methyl sulfate and p-toluene sulfonate. 2
6. A compound according to Claim 2k wherein R-^ is methyl; P is alkyl, C1-CZ) ; Y , Y ' , Z and Z' each independently represent a member selected from the group consisting of hydrogen, halogen, methyl and methoxy; provided that only one of the phenyl rings is substituted para to the pyrazolium ring with a substituent other than hydrogen. 40968/3 2
7. The compound according to Claim 24: 1;2-dimethyl- 3,5-diphenylpyrazolium methyl sulfate. 2
8. The compound according to claim 24: 1 ,2-dimethyl- 3,5-diph^nylpyrazolium p_-toluenesulfonate. 2
9. . The compound according to claim 24: 1 ,2-dimethyl-3- (m-methylphenyl) -5-phenylpyrazolium.methyl sulfate. 30. A method for the preparation of a compound according to claim 24 characterized by the steps of: reacting a ketone of the . formula wherein Y, Y', Z and Z' 'are asi defined in claim 24 with a compound of the formula RNHNH- wherein R is hydrogen or lower alkyl, to form the corresponding 3,5-diphenylpyrazole; and (b) where R is lower alkyl, reacting said pyrazole with an equimolar amount of an alkylating agent fo form the corresponding pyrazolium salt of claim 24; and (c) where R is hydrogen, simultaneously or . consecutively reacting said pyrazole with two molar equivalents of one or two alkylating agents to form the corresponding pyrazolium salt of claim 24. 31. A method according to claim 30, wherein the alkylating agent is dimethyl sulfate and Y, Y1, Z and Z' are hydrogen and R is methyl. 32. A method for the preparation of a compound according to claim 24 comprising the anion exchange of a pyrazolium salt of the formula: 40968/2 wherein R^,- R2, Y, Υ' , Ζ and Ζ' are as defined. in claim 24, W is an anion and m1 is an integer selected from 1, 2 and 3. 33. A method according to claim 1 for the control of undesirable plant species, substantially as hereinbefore described. 34. Herbicidal compositions according to claim 21, substantially as hereinbefore described. 35. Compounds according to claim 24 substantially as hereinbefore described. 36. Water-miscible herbicidal concentrates, according to claim 20, substantially as hereinbefore described. S.HOROWITZ S C0< AGENTS FOR APPLICANTS
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20944871A | 1971-12-17 | 1971-12-17 | |
| US27142472A | 1972-07-13 | 1972-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40968A0 IL40968A0 (en) | 1973-01-30 |
| IL40968A true IL40968A (en) | 1976-02-29 |
Family
ID=26904186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40968A IL40968A (en) | 1971-12-17 | 1972-11-30 | Herbicidal compositions containing 1,2-dialkyl-3,5-diaryl pyrazolium salts,some novel pyrazolium salts and process for preparing the same |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS587627B2 (en) |
| AR (1) | AR213380A1 (en) |
| AT (1) | AT322270B (en) |
| BE (1) | BE792801A (en) |
| BG (1) | BG20760A3 (en) |
| CA (1) | CA1020165A (en) |
| CH (1) | CH578323A5 (en) |
| CS (1) | CS196245B2 (en) |
| CY (1) | CY942A (en) |
| DD (1) | DD105383A5 (en) |
| DK (1) | DK132203C (en) |
| ES (1) | ES409722A1 (en) |
| FI (1) | FI55752C (en) |
| FR (1) | FR2163473B1 (en) |
| GB (1) | GB1407278A (en) |
| HK (1) | HK8678A (en) |
| IE (1) | IE37196B1 (en) |
| IL (1) | IL40968A (en) |
| IT (1) | IT974004B (en) |
| MY (1) | MY7800191A (en) |
| NL (1) | NL175018C (en) |
| NO (1) | NO136388C (en) |
| RO (1) | RO66012A (en) |
| SE (1) | SE400453B (en) |
| TR (1) | TR17283A (en) |
| YU (2) | YU39457B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2404795C2 (en) * | 1974-02-01 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | 1,2-Dimethyl-3,5-diphenylpyrazolium salts and their use as herbicides |
| US3910949A (en) * | 1974-12-09 | 1975-10-07 | American Cyanamid Co | Manufacture of 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate in a single reaction zone |
| FR2418625A2 (en) * | 1978-03-03 | 1979-09-28 | British Petroleum Co | Compsns. contg. difenzoquat and petroleum fraction - selective herbicide for wheat, barley and winter barley |
-
0
- BE BE792801D patent/BE792801A/en not_active IP Right Cessation
-
1972
- 1972-11-30 DK DK600272A patent/DK132203C/en not_active IP Right Cessation
- 1972-11-30 IL IL40968A patent/IL40968A/en unknown
- 1972-11-30 SE SE7215642A patent/SE400453B/en unknown
- 1972-11-30 IE IE1664/72A patent/IE37196B1/en unknown
- 1972-12-01 GB GB5568072A patent/GB1407278A/en not_active Expired
- 1972-12-01 CY CY942A patent/CY942A/en unknown
- 1972-12-05 CA CA158,079A patent/CA1020165A/en not_active Expired
- 1972-12-05 FR FR7243254A patent/FR2163473B1/fr not_active Expired
- 1972-12-06 AR AR245501A patent/AR213380A1/en active
- 1972-12-11 IT IT54623/72A patent/IT974004B/en active
- 1972-12-12 TR TR17283A patent/TR17283A/en unknown
- 1972-12-12 BG BG022080A patent/BG20760A3/en unknown
- 1972-12-14 CH CH1825372A patent/CH578323A5/xx not_active IP Right Cessation
- 1972-12-14 NL NLAANVRAGE7217015,A patent/NL175018C/en not_active IP Right Cessation
- 1972-12-15 NO NO4653/72A patent/NO136388C/en unknown
- 1972-12-15 AT AT1072372A patent/AT322270B/en not_active IP Right Cessation
- 1972-12-15 DD DD167594A patent/DD105383A5/xx unknown
- 1972-12-15 FI FI3562/72A patent/FI55752C/en active
- 1972-12-16 ES ES409722A patent/ES409722A1/en not_active Expired
- 1972-12-16 RO RO7273175A patent/RO66012A/en unknown
- 1972-12-18 JP JP47127053A patent/JPS587627B2/en not_active Expired
- 1972-12-18 YU YU281281A patent/YU39457B/en unknown
- 1972-12-18 CS CS728729A patent/CS196245B2/en unknown
- 1972-12-18 YU YU03151/72A patent/YU315172A/en unknown
-
1978
- 1978-02-16 HK HK86/78A patent/HK8678A/en unknown
- 1978-12-30 MY MY191/78A patent/MY7800191A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT322270B (en) | 1975-05-12 |
| NO136388C (en) | 1977-08-31 |
| IE37196L (en) | 1973-06-17 |
| NL175018B (en) | 1984-04-16 |
| TR17283A (en) | 1975-03-24 |
| CY942A (en) | 1978-06-23 |
| SE400453B (en) | 1978-04-03 |
| BE792801A (en) | 1973-06-15 |
| ES409722A1 (en) | 1976-04-01 |
| BG20760A3 (en) | 1975-12-20 |
| FI55752B (en) | 1979-06-29 |
| FR2163473B1 (en) | 1977-01-14 |
| IT974004B (en) | 1974-06-20 |
| CS196245B2 (en) | 1980-03-31 |
| MY7800191A (en) | 1978-12-31 |
| DK132203B (en) | 1975-11-10 |
| DK132203C (en) | 1976-04-12 |
| YU39457B (en) | 1984-12-31 |
| NL7217015A (en) | 1973-06-19 |
| GB1407278A (en) | 1975-09-24 |
| CA1020165A (en) | 1977-11-01 |
| RO66012A (en) | 1981-08-30 |
| DD105383A5 (en) | 1974-04-20 |
| IE37196B1 (en) | 1977-05-25 |
| CH578323A5 (en) | 1976-08-13 |
| NO136388B (en) | 1977-05-23 |
| JPS4872329A (en) | 1973-09-29 |
| FI55752C (en) | 1979-10-10 |
| JPS587627B2 (en) | 1983-02-10 |
| FR2163473A1 (en) | 1973-07-27 |
| AR213380A1 (en) | 1979-01-31 |
| NL175018C (en) | 1984-09-17 |
| YU315172A (en) | 1982-02-28 |
| IL40968A0 (en) | 1973-01-30 |
| HK8678A (en) | 1978-02-24 |
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