CA1047534A - Haloacetanilides for influencing plant growth - Google Patents
Haloacetanilides for influencing plant growthInfo
- Publication number
- CA1047534A CA1047534A CA191,039A CA191039A CA1047534A CA 1047534 A CA1047534 A CA 1047534A CA 191039 A CA191039 A CA 191039A CA 1047534 A CA1047534 A CA 1047534A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- dimethyl
- compound according
- ethyl
- methyl
- 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
- 230000008635 plant growth Effects 0.000 title abstract 2
- -1 alkyl radical Chemical class 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005977 Ethylene Substances 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Chemical group 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- RMCDUNHIVVEEDD-UHFFFAOYSA-N methylcyclopropane Chemical compound [CH2]C1CC1 RMCDUNHIVVEEDD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 241000196324 Embryophyta Species 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 244000038559 crop plants Species 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 229940093470 ethylene Drugs 0.000 claims 4
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 51
- 239000000969 carrier Substances 0.000 abstract description 9
- 239000002270 dispersing agent Substances 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000006072 paste Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 241000209504 Poaceae Species 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 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 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000008187 granular material Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000209094 Oryza Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 235000021186 dishes Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 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 3
- 239000002245 particle Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- HRRMPGSFIAVSNM-UHFFFAOYSA-N 3-bromo-2,6-dimethylaniline Chemical compound CC1=CC=C(Br)C(C)=C1N HRRMPGSFIAVSNM-UHFFFAOYSA-N 0.000 description 2
- FUCUHFQBEBZAFY-UHFFFAOYSA-N 6-ethyl-2,3-dimethylaniline Chemical compound CCC1=CC=C(C)C(C)=C1N FUCUHFQBEBZAFY-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- OOMXGFUBBBFWHR-UHFFFAOYSA-N O.SS Chemical compound O.SS OOMXGFUBBBFWHR-UHFFFAOYSA-N 0.000 description 2
- 235000005775 Setaria Nutrition 0.000 description 2
- 241000232088 Setaria <nematode> Species 0.000 description 2
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- 235000021536 Sugar beet Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 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
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| CH175773A CH582470A5 (en)) | 1973-02-07 | 1973-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047534A true CA1047534A (en) | 1979-01-30 |
Family
ID=4217851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,039A Expired CA1047534A (en) | 1973-02-07 | 1974-01-28 | Haloacetanilides for influencing plant growth |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS49109530A (en)) |
| AT (1) | AT338554B (en)) |
| BE (1) | BE810670A (en)) |
| BG (1) | BG20755A3 (en)) |
| BR (1) | BR7400845D0 (en)) |
| CA (1) | CA1047534A (en)) |
| CH (1) | CH582470A5 (en)) |
| CS (1) | CS177160B2 (en)) |
| DD (2) | DD118617A5 (en)) |
| DE (1) | DE2405183A1 (en)) |
| ES (1) | ES422953A1 (en)) |
| FR (1) | FR2215899B1 (en)) |
| GB (1) | GB1455471A (en)) |
| HU (1) | HU167576B (en)) |
| IL (1) | IL44098A (en)) |
| IT (1) | IT1048110B (en)) |
| NL (1) | NL7401571A (en)) |
| PH (1) | PH11121A (en)) |
| PL (1) | PL94680B1 (en)) |
| SU (1) | SU581837A3 (en)) |
| ZA (1) | ZA74767B (en)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2825543A1 (de) * | 1978-06-10 | 1979-12-13 | Bayer Ag | N-substituierte halogenacetanilide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| FR2479198A1 (fr) * | 1980-03-25 | 1981-10-02 | Monsanto Co | Procede de preparation de 2-haloacetanilides a substitution alcoxy en position ortho, nouveaux produits ainsi obtenus et leur utilisation comme herbicides |
| US4721797A (en) * | 1986-09-02 | 1988-01-26 | Ciba-Geigy Corporation | Process for the preparation of N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines |
-
1973
- 1973-02-07 CH CH175773A patent/CH582470A5/xx not_active IP Right Cessation
-
1974
- 1974-01-28 IL IL44098A patent/IL44098A/en unknown
- 1974-01-28 CA CA191,039A patent/CA1047534A/en not_active Expired
- 1974-02-04 FR FR7403618A patent/FR2215899B1/fr not_active Expired
- 1974-02-04 SU SU7401990653A patent/SU581837A3/ru active
- 1974-02-04 CS CS738A patent/CS177160B2/cs unknown
- 1974-02-04 DE DE19742405183 patent/DE2405183A1/de not_active Withdrawn
- 1974-02-05 DD DD184319A patent/DD118617A5/xx unknown
- 1974-02-05 NL NL7401571A patent/NL7401571A/xx not_active Application Discontinuation
- 1974-02-05 DD DD176386A patent/DD110746A5/xx unknown
- 1974-02-06 ZA ZA740767A patent/ZA74767B/xx unknown
- 1974-02-06 BE BE140601A patent/BE810670A/xx not_active IP Right Cessation
- 1974-02-06 PL PL1974168611A patent/PL94680B1/pl unknown
- 1974-02-06 GB GB544974A patent/GB1455471A/en not_active Expired
- 1974-02-06 AT AT92474A patent/AT338554B/de not_active IP Right Cessation
- 1974-02-06 HU HUCI1442A patent/HU167576B/hu unknown
- 1974-02-06 PH PH15481A patent/PH11121A/en unknown
- 1974-02-06 BR BR74845A patent/BR7400845D0/pt unknown
- 1974-02-06 IT IT20254/74A patent/IT1048110B/it active
- 1974-02-06 BG BG25712A patent/BG20755A3/xx unknown
- 1974-02-06 ES ES422953A patent/ES422953A1/es not_active Expired
- 1974-02-07 JP JP49015821A patent/JPS49109530A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49109530A (en)) | 1974-10-18 |
| CS177160B2 (en)) | 1977-07-29 |
| DD110746A5 (en)) | 1975-01-12 |
| SU581837A3 (ru) | 1977-11-25 |
| IL44098A (en) | 1977-10-31 |
| ZA74767B (en) | 1974-12-24 |
| ATA92474A (de) | 1976-12-15 |
| PL94680B1 (pl) | 1977-08-31 |
| GB1455471A (en) | 1976-11-10 |
| NL7401571A (en)) | 1974-08-09 |
| AU6505174A (en) | 1975-07-31 |
| BG20755A3 (en)) | 1975-12-20 |
| AT338554B (de) | 1977-09-12 |
| HU167576B (en)) | 1975-11-28 |
| FR2215899A1 (en)) | 1974-08-30 |
| DE2405183A1 (de) | 1974-08-08 |
| CH582470A5 (en)) | 1976-12-15 |
| IL44098A0 (en) | 1974-05-16 |
| IT1048110B (it) | 1980-11-20 |
| PH11121A (en) | 1977-10-27 |
| ES422953A1 (es) | 1977-01-01 |
| FR2215899B1 (en)) | 1976-06-25 |
| DD118617A5 (en)) | 1976-03-12 |
| BE810670A (fr) | 1974-08-06 |
| BR7400845D0 (pt) | 1974-11-26 |
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