CA1081701A - 3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables - Google Patents

3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables

Info

Publication number: CA1081701A
Authority: CA; Canada
Prior art keywords: delta; methylimino; thiadiazoline; benzyl; chloro
Prior art date: 1977-04-26
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

CA277,042A

Other languages

English (en)

Inventor

Norman A. Dahle

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.)

Gulf Oil Corp

Original Assignee

Gulf Oil Corp

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.)

1977-04-26

Filing date

1977-04-26

Publication date

1980-07-15

1977-04-26 Application filed by Gulf Oil Corp filed Critical Gulf Oil Corp

1977-04-26 Priority to CA277,042A priority Critical patent/CA1081701A/fr

1980-07-15 Application granted granted Critical

1980-07-15 Publication of CA1081701A publication Critical patent/CA1081701A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 22
230000008635 plant growth Effects 0.000 title description 2
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 19
241000196324 Embryophyta Species 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
150000003839 salts Chemical group 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 3
241000209140 Triticum Species 0.000 abstract description 6
235000021307 Triticum Nutrition 0.000 abstract description 6
235000013339 cereals Nutrition 0.000 abstract description 5
240000007594 Oryza sativa Species 0.000 abstract description 2
235000007164 Oryza sativa Nutrition 0.000 abstract description 2
235000009566 rice Nutrition 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 13
239000004009 herbicide Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
239000002198 insoluble material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000021536 Sugar beet Nutrition 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
208000014674 injury Diseases 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002689 soil Substances 0.000 description 3
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
BVPHNVDCIYWQPL-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-methyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(NC)=NN=C1C1=CC=CC(Cl)=C1 BVPHNVDCIYWQPL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
238000003828 vacuum filtration Methods 0.000 description 2
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical group CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
UYQPSKUPEXAQRJ-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylmethoxybenzene Chemical compound C1=CC(CCl)=CC=C1OCC1=CC=CC=C1 UYQPSKUPEXAQRJ-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
-1 4-methylbenzyl compound Chemical class 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
244000088415 Raphanus sativus Species 0.000 description 1
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
WWHUBDJBTAYJMC-UHFFFAOYSA-N n-methylthiadiazol-4-imine Chemical class CN=C1CSN=N1 WWHUBDJBTAYJMC-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920006327 polystyrene foam Polymers 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
208000037974 severe injury Diseases 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
VDZXAOBGHPKGCS-UHFFFAOYSA-M sodium;1,4-dioxane;hydroxide Chemical compound [OH-].[Na+].C1COCCO1 VDZXAOBGHPKGCS-UHFFFAOYSA-M 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA277,042A 1977-04-26 1977-04-26 3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables Expired CA1081701A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA277,042A CA1081701A (fr)	1977-04-26	1977-04-26	3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA277,042A CA1081701A (fr)	1977-04-26	1977-04-26	3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables

Publications (1)

Publication Number	Publication Date
CA1081701A true CA1081701A (fr)	1980-07-15

Family

ID=4108508

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA277,042A Expired CA1081701A (fr)	1977-04-26	1977-04-26	3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables

Country Status (1)

Country	Link
CA (1)	CA1081701A (fr)

1977
- 1977-04-26 CA CA277,042A patent/CA1081701A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-07-15	MKEX	Expiry

Publication	Publication Date	Title
KR850001951B1 (ko)	1985-12-31	N-아릴벤즈아미드 유도체의 제조방법
EP0020052B1 (fr)	1983-07-20	Nitrodiphényl éthers substitués, compositions herbicides les contenant, procédé pour leur préparation et leur utilisation pour combattre les mauvaises herbes
US3770754A (en)	1973-11-06	Certai 1,2,4-oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives
KR800000505B1 (ko)	1980-06-12	1-티아디아 졸리이미다 졸리딘온의 제조방법
SU963465A3 (ru)	1982-09-30	Способ получени гетероциклических фениловых эфиров и его варианты
CS211368B2 (en)	1982-02-26	Means with herbicide,growth regulating,fungicide effect
HU208226B (en)	1993-09-28	Herbicidal compositions comprising pyrrolidine-2,5-dione or 4,5,6,7-tetrahydroisoindole-1,3-dione derivatives as active ingredient and process for producing the active ingredient
CA1081701A (fr)	1980-07-15	3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines et lutte contre les plantes indesirables
US4098600A (en)	1978-07-04	Isocyanoacylamides
US4742072A (en)	1988-05-03	1-dimethylcarbamoyl-3-t-butyl-5-substituted-1H-1,2,4-triazoles
US4346225A (en)	1982-08-24	Herbicidal 2-methylamino thiadiazolines
US4020078A (en)	1977-04-26	3-Benzyl-2-methylimino-5-phenyl-delta-4-1,3,4-thiadiazolines
US4264502A (en)	1981-04-28	N-(arylthiocarbamoyl)-2-amino-1H-isoindole-1,3-(2H)diones and use as plant growth regulators
CA1146945A (fr)	1983-05-24	Regulateurs de croissance vegetale, a base de phenyliminothiadiazolines
JPS5934187B2 (ja)	1984-08-21	α↓−ハロアセトアミド化合物および除草剤
USRE29439E (en)	1977-10-11	Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives
US4104053A (en)	1978-08-01	3-Benzyl-2-methylimino-5-phenyl-Δ4 -1,3,4-thiadiazolines and method of combating undesired plant growth
KR910002672B1 (ko)	1991-05-03	페닐아세트아닐리드 유도체의 제조방법
CA1125766A (fr)	1982-06-15	Imides derives de l'acide 2-oxo-3-benzothiazoline acetique et de l'acide butyrique
US4330322A (en)	1982-05-18	N-(Arylthiocarbamoyl)-2-amino-1H-isoindole-1,3,-(2H) dione plant growth regulators
KR790001256B1 (ko)	1979-09-18	1, 2, 4-트리아졸리딘-3-온 유도체의 제조방법
US4292071A (en)	1981-09-29	Isothioureido isoindolediones and use as plant growth regulators
US4308052A (en)	1981-12-29	N-Substituted benzothiazolines substituted with thiol esters useful as herbicides and plant growth regulants
EP0019369B1 (fr)	1984-03-07	Isothiouréidoisoindolediones, procédé pour leur préparation et leur utilisation comme régulateurs de croissance des végétaux
GB2048246A (en)	1980-12-10	N-(arylthiocarbamoyl)-2-amino-1h-isoindole-1,3-(2h)diones and their use as plant growth regulators