GB951770A - Improvements in or relating to combating pests - Google Patents
Improvements in or relating to combating pestsInfo
- Publication number
- GB951770A GB951770A GB14775/60A GB1477560A GB951770A GB 951770 A GB951770 A GB 951770A GB 14775/60 A GB14775/60 A GB 14775/60A GB 1477560 A GB1477560 A GB 1477560A GB 951770 A GB951770 A GB 951770A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dinitro
- parts
- nitro
- preparation
- trichlorobenzonitrile
- Prior art date
- 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
Links
- 241000607479 Yersinia pestis Species 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- 238000002360 preparation method Methods 0.000 abstract 6
- 239000013543 active substance Substances 0.000 abstract 5
- 229910000514 dolomite Inorganic materials 0.000 abstract 5
- 239000010459 dolomite Substances 0.000 abstract 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 4
- CDENXACHOQGZKZ-UHFFFAOYSA-N 2,4,6-trichloro-3,5-dinitrobenzonitrile Chemical compound [N+](=O)([O-])C=1C(=C(C#N)C(=C(C1Cl)[N+](=O)[O-])Cl)Cl CDENXACHOQGZKZ-UHFFFAOYSA-N 0.000 abstract 3
- SCGDEDHSPCXGEC-UHFFFAOYSA-N 4-chloro-3,5-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC([N+]([O-])=O)=C1Cl SCGDEDHSPCXGEC-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 241000894006 Bacteria Species 0.000 abstract 3
- 241000233866 Fungi Species 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- ZYDGHQSJZAFMLU-UHFFFAOYSA-N 2,6-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1C#N ZYDGHQSJZAFMLU-UHFFFAOYSA-N 0.000 abstract 2
- DQEOUPUFGJBXFK-UHFFFAOYSA-N 4,5-dichloro-2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1C#N DQEOUPUFGJBXFK-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 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 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000000428 dust Substances 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- -1 fatty acid ester Chemical class 0.000 abstract 2
- 229920005610 lignin Polymers 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 239000002245 particle Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 229940104261 taurate Drugs 0.000 abstract 2
- 239000004563 wettable powder Substances 0.000 abstract 2
- BGKIECJVXXHLDP-UHFFFAOYSA-N 1,2,3-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1Cl BGKIECJVXXHLDP-UHFFFAOYSA-N 0.000 abstract 1
- RDFDRMZYAXQLRT-UHFFFAOYSA-N 2,3-dichloro-6-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1C#N RDFDRMZYAXQLRT-UHFFFAOYSA-N 0.000 abstract 1
- UUDSOIHVZPPQAA-UHFFFAOYSA-N 2,4,6-trichloro-3,5-dinitrobenzoic acid Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)O)C(=C(C1Cl)[N+](=O)[O-])Cl)Cl UUDSOIHVZPPQAA-UHFFFAOYSA-N 0.000 abstract 1
- PGODHCIOIPODFE-UHFFFAOYSA-N 2,4,6-trichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Cl)=C1 PGODHCIOIPODFE-UHFFFAOYSA-N 0.000 abstract 1
- CWTFEEDMVMXTDU-UHFFFAOYSA-N 2,5-dinitrobenzamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O CWTFEEDMVMXTDU-UHFFFAOYSA-N 0.000 abstract 1
- BUDYMWWQYLMHBU-UHFFFAOYSA-N 2,5-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C(C#N)=C1 BUDYMWWQYLMHBU-UHFFFAOYSA-N 0.000 abstract 1
- AILZELNZMCLRSA-UHFFFAOYSA-N 2,6-dichloro-3,5-dinitrobenzonitrile Chemical compound [N+](=O)([O-])C=1C(=C(C#N)C(=C(C1)[N+](=O)[O-])Cl)Cl AILZELNZMCLRSA-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 abstract 1
- UPPCKWMSUQKZRI-UHFFFAOYSA-N 2-chloro-4,6-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(Cl)=C(C#N)C([N+]([O-])=O)=C1 UPPCKWMSUQKZRI-UHFFFAOYSA-N 0.000 abstract 1
- NBGXBBVTAHZWEN-UHFFFAOYSA-N 3,4,5-trichloro-2,6-dinitrobenzonitrile Chemical compound [N+](=O)([O-])C1=C(C#N)C(=C(C(=C1Cl)Cl)Cl)[N+](=O)[O-] NBGXBBVTAHZWEN-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 235000007849 Lepidium sativum Nutrition 0.000 abstract 1
- 244000211187 Lepidium sativum Species 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- YLZGVPCTROQQSX-UHFFFAOYSA-N [K].[Ni](C#N)C#N Chemical compound [K].[Ni](C#N)C#N YLZGVPCTROQQSX-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000000642 acaricide Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 229960000892 attapulgite Drugs 0.000 abstract 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 230000035784 germination Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052625 palygorskite Inorganic materials 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 235000010333 potassium nitrate Nutrition 0.000 abstract 1
- 239000004323 potassium nitrate Substances 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
Abstract
Nitro-chloro-benzonitriles of the general formula: <FORM:0951770/C2/1> where p=1 or 2, and p+q=5, may be produced by a series of reactions starting from the appropriate polychloro-benzonitrile or the appropriate nitro-polychlorobenzoic acid. In Example 10, potassium nitrate is added to a solution of 2,4,6-trichlorobenzonitrile in concentrated sulphuric acid. The mixture is heated for one hour, and then poured on ice and water whereby 3,5-dinitro-2,4,6-trichlorobenzoic acid is obtained. This acid is converted, via the acid-chloride, into the corresponding benzamide, which is then heated with phosphorus ocychloride to give 3,5-dinitro-2,4,6-trichlorobenzonitrile. Example 11 describes the preparation of 2,6-dinitro-3,4,5-trichlorobenzonitrile by heating the corresponding benzamide with a mixture of phosphorus oxychloride and sodium dithionite. The Specification also relates to nitro-chloro-benzonitriles outside the scope of the above formula. In Example 3, diazotised 2,4-dinitro-6-chloroaniline is treated with potassium nickel cyanide to give 2,4-dinitro-6-chlorobenzonitrile. Example 4 describes the preparation of 2-nitro-5,6-dichloro-benzonitrile by the action of cuprous cyanide on 2,3,4-trichloronitrobenzene. Examples 1, 2, 8 and 9 relate to the preparation of three isomeric mononitro-trichlorobenzonitriles. Examples 5 and 7 relate to the preparation of 3,5-dinitro-2,6-dichlorobenzonitrile and 3,5-dinitro-4-chlorobenzonitrile, respectively. Example 6 describes the preparation of 2,5-dinitrobenzonitrile by dehydration of 2,5-dinitrobenzamide. All these compounds have use in the preparation of compositions for combating fungi and bacteria.ALSO:The invention comprises compositions for combating pests, such as fungi and bacteria, containing as an active substance a compound of the general formula <FORM:0951770/A5-A6/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p=1 or 2, q=1, 2, 3 or 4 when p=1, or q=0, 1, 2, 3 or 4 when p=2, and r=0, 1, 2 or 3. Specified solid carriers are: chalk, dolomite, attapulgite, china clay and pipe clay. Specific liquid carriers are: toluene, xylene, petroleum ether, acetone, methyl ethyl ketone and cyclohexanone. The compositions may incorporate insecticides, acaricides, fertilizers, surface-active agents, dispersion agents, and adhesives. A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile (5 parts), kieselguhr (10 parts) and dolomite 85 parts), together to a mean particle size of about 10 microns. A wettable powder may be produced by mixing 3,5-dinitro-2,4,6-trichlorobenzonitrile (20 parts), p dolomite (73 parts), oleylamido-methyl-taurate (2 parts), and sodium lignin sulphonate (5 parts), and grinding the mixture to a mean particle size of about 10 microns. A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile (10 parts) in a mixture of toluene (12 parts), methyl ethyl ketone (72 parts), and polyoxyethylenesorbitane fatty acid ester (6 parts). A dinitrobenzonitrile can also be used as active substance.ALSO:Pests such as fungi and bacteria are combated by treating seeds with a composition comprising as an active substance a compound of the general formula <FORM:0951770/A1-A3/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p = 1 or 2, q = 1, 2, 3 or 4 when p = 1, or q = 0, 1, 2, 3 or 4 when p = 2, and r = 0, 1, 2 or 3. From tests with the seed of garden cress and a few monocotyledonous plants it has been found that the active substances do not retard germination. A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile, kieselguhr, and dolomite together. A wettable powder may be produced by grinding 3,5-dinitro-2,4,6-trichlorobenzonitrile, dolomite, oleylamido-methyl-taurate, and sodium lignin sulphonate together. A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile in a mixture of toluene, methyl ethyl ketone, and polyoxyethylenesorbitane fatty acid ester. A dinitro-benzonitrile can also be used as an active substance.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL238687 | 1959-04-28 | ||
NL242085 | 1959-08-06 | ||
NL249879 | 1960-03-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB951770A true GB951770A (en) | 1964-03-11 |
Family
ID=27351015
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB14775/60A Expired GB951770A (en) | 1959-04-28 | 1960-04-27 | Improvements in or relating to combating pests |
GB14772/60A Expired GB949619A (en) | 1959-04-28 | 1960-04-27 | Improvements in or relating to nuclear-chlorinated benzonitrile derivatives and compositions comprising the same |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB14772/60A Expired GB949619A (en) | 1959-04-28 | 1960-04-27 | Improvements in or relating to nuclear-chlorinated benzonitrile derivatives and compositions comprising the same |
Country Status (8)
Country | Link |
---|---|
US (1) | US3185725A (en) |
BE (2) | BE590254A (en) |
CH (1) | CH401024A (en) |
DE (1) | DE1143802B (en) |
DK (1) | DK105016C (en) |
ES (1) | ES257609A1 (en) |
GB (2) | GB951770A (en) |
NL (4) | NL108786C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6399807B1 (en) | 1997-07-01 | 2002-06-04 | Bayer Aktiegesellschaft | Method for production of 2,4,5-trifluoro-benzonitrile |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3535365A (en) * | 1967-11-29 | 1970-10-20 | Merck & Co Inc | Preparation of 2,6-dichloro-4-methoxy-benzonitrile |
DE2960235D1 (en) * | 1978-06-12 | 1981-04-23 | Nippon Kayaku Kk | A process for the production of 2-chlorobenzonitrile derivatives |
JPS55120549A (en) * | 1979-03-09 | 1980-09-17 | Nippon Kayaku Co Ltd | Preparation of 2-chloro-6-nitrobenzonitrile |
JPS5998052A (en) * | 1982-11-26 | 1984-06-06 | Sanwa Kagaku Kenkyusho:Kk | Preparation of 4-chloro-2-nitrobenzonitrile |
JPH0625097B2 (en) * | 1988-03-19 | 1994-04-06 | 出光興産株式会社 | Method for producing aromatic nitrile |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1996007A (en) * | 1933-07-27 | 1935-03-26 | Du Pont | Preparation of-2-chloro-6-nitro-benzaldoxime |
US2195076A (en) * | 1936-10-24 | 1940-03-26 | Gen Aniline & Film Corp | Process of replacing halogen in cyclic halogen compounds and product thereof |
GB488642A (en) * | 1936-11-05 | 1938-07-05 | Ig Farbenindustrie Ag | A process for the replacement of halogen in cyclic halogen compounds by the cyano group |
DE843327C (en) * | 1947-03-18 | 1952-07-07 | Bayer Products Ltd | Combating diseases in potato tubers |
US2497060A (en) * | 1948-12-31 | 1950-02-14 | Gen Aniline & Film Corp | 3,5-dihalogen-2-cyanodiphenyls |
US2671798A (en) * | 1949-04-09 | 1954-03-09 | Merck & Co Inc | 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same |
US2690965A (en) * | 1953-04-29 | 1954-10-05 | Standard Oil Dev Co | Herbicidal composition |
US2744819A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method for the control of undesired grasses |
US3006954A (en) * | 1957-12-27 | 1961-10-31 | Shell Oil Co | Urea and thiourea compounds |
US3012058A (en) * | 1958-05-15 | 1961-12-05 | Pennsalt Chemicals Corp | Nitrile compounds |
US3009942A (en) * | 1958-07-02 | 1961-11-21 | Heyden Newport Chemical Corp | Production of trichlorobenzoic acids |
US2999046A (en) * | 1958-08-25 | 1961-09-05 | Diamond Alkali Co | Method of destroying fungi and nematodes employing 2, 2'-(p-xylene)-bis-[2-thiopseudourea] dihydrochloride |
-
0
- BE BE590258D patent/BE590258A/xx unknown
- BE BE590254D patent/BE590254A/xx unknown
- NL NL238687D patent/NL238687A/xx unknown
- NL NL242085D patent/NL242085A/xx unknown
- NL NL104318D patent/NL104318C/xx active
- NL NL108786D patent/NL108786C/xx active
-
1960
- 1960-04-25 CH CH465160A patent/CH401024A/en unknown
- 1960-04-25 ES ES0257609A patent/ES257609A1/en not_active Expired
- 1960-04-26 DE DEN18228A patent/DE1143802B/en active Pending
- 1960-04-26 DK DK161360AA patent/DK105016C/en active
- 1960-04-27 GB GB14775/60A patent/GB951770A/en not_active Expired
- 1960-04-27 GB GB14772/60A patent/GB949619A/en not_active Expired
- 1960-04-27 US US24916A patent/US3185725A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6399807B1 (en) | 1997-07-01 | 2002-06-04 | Bayer Aktiegesellschaft | Method for production of 2,4,5-trifluoro-benzonitrile |
Also Published As
Publication number | Publication date |
---|---|
NL242085A (en) | |
ES257609A1 (en) | 1960-09-16 |
DE1143802B (en) | 1963-02-21 |
NL104318C (en) | |
GB949619A (en) | 1964-02-12 |
BE590254A (en) | |
BE590258A (en) | |
NL108786C (en) | |
DK105016C (en) | 1966-08-08 |
CH401024A (en) | 1965-10-31 |
US3185725A (en) | 1965-05-25 |
NL238687A (en) |
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